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| 1.
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Somei, Masanori ; Yamada, Fumio ; Yamazaki, Yoshihisa ; Shinkura, Akiko
概要:
We developed a novel synthesis of 2-aminoindan derivatives, having a 2-methyl-1-propenyl group at the 1-position and oxygen functional groups in the benzene ring, in 8 or 9 steps from vanillin.
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| 2.
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Yamada, Fumio ; Kawanishi, Atsuko ; Tomita, Akiko ; Somei, Masanori
概要:
1-Hydroxy-2,3-dimethylindole (1) has been prepared for the first time. Under atmospheric oxygen, 1 was converted rapidly into 3-hydroxy-2,3-dimethyl- 3H-indole N-oxide (2). The structure was deduced, based on its products obtained
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by the reaction with Ac2O in pyridine and confirmed by X-ray single crystallographic analysis.
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| 3.
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Somei, Masanori ; Hayashi, Hiroyuki ; Ohmoto, Shinobu
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Indigo was converted to 2,2′-bisindole by the direct reduction with zinc in ace
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tic acid and acetic anhydride under argon or hydrogen atmosphere. Reduction with tin and iron afforded 3-acetoxy-2,2′-bisindole predominantly. Useful building blocks such as 1-acetyl-2,3-dihydro-, 3-acetoxy-3′-acetyl-, and 3-acetoxy-1,3′-diacetyl-2,2′-bisindoles were also produced depending on metal and reaction conditions.
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| 4.
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Somei, Masanori ; Kodama, Atsushi
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 5.
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Yamada, Koji ; Somei, Masanori
概要:
Photoirradiation of 1-ethoxy-2-phenylindole in methanol and the reaction of 1-hydroxy-2-phenylindole with tosyl chloride
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produced 6-ethoxy- and 6-tosyloxy-2-phenylindoles, respectively, as minor products. The latter was derived to 6-ethoxy-2-phenylindole. The structure is determined by direct comparison of the spectral data with those of the authentic 4-, 5-, 6-, and 7-ethoxy-2-phenylindoles whose syntheses are reported in detail. © 2012 The Japan Institute of Heterocyclic Chemistry.
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| 6.
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Yamada, Fumio ; Fukui, Yoshikazu ; Iwaki, Takako ; Ogasawara, Sachiko ; Okigawa, Masaki ; Tanaka, Satomi ; Somei, Masanori
概要:
A simple and new method for the preparation of optically active methyl 3a-chloro-, 3a-bromo-, 3a-hydroxy-, and 3a-alkoxy
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-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylates has been developed. © 2006 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 7.
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Fukui, Yoshikazu ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />3-Substituted (3S,6S)-6-(1-hydroxyindol-3-ylmethyl)-2,5-piperazinediones are pr
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epared for the first time. They are shown to be suitable intermediates for the synthesis of 3,10b-disubstituted (3S,5aR,10bS,11as)-1,3,4,5a,6,10b,11, 11a-octahydro-2H-pyrazino[1',2': 1,5]pyrrolo[2,3-b]indole-1,4-dione derivatives.
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| 8.
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Somei, Masanori ; Kobayashi, Tetsuya
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 9.
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Yamada, Fumio ; Goto, Aya ; Hasegawa, Masakazu ; Kobayashi, Kensuke ; Somei, Masanori ; 山田, 文夫 ; 染井, 正徳
概要:
金沢大学医薬保健研究域薬学系<br />Various nucleophiles, such as indole, 1,2,3-trimethoxybenzene, anisole, phenol, and pyrrole, reacted
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with 1-hydroxy-Nb-trifluoroacetyltryptamine under the presence of mesyl chloride to give novel series of (3a,8acis)- 1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles having a substituent at the 3aposition. Their structures and by-products were strictly determined. © 2017 The Japan Institute of Heterocyclic Chemistry.<br />Embargo Period 12 months
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| 10.
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Somei, Masanori ; Hayashi, Hiroyuki ; Izumi, Tohru ; Ohmoto, Shinobu
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 11.
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Yamada, Koji ; Yamada, Fumio ; Shiraishi, Takei ; Tomioka, Saori ; Somei, Masanori
概要:
1-Methoxy-6-nitroindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-pos
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ition with various types of nucleophiles providing 2,3,6-trisubstituted indole derivatives. The reaction is applicable for the preparation of a novel pyrimido[1,2-a]indole derivative. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 12.
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Yamada, Fumio ; Fukui, Yoshikazu ; Iwaki, Takako ; Ogasawara, Sachiko ; Okigawa, Masaki ; Tanaka, Satomi ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A simple and new method for the preparation of optically active methyl 3a-chlor
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o-, 3a-bromo-, 3a-hydroxy-, and 3a-alkoxy-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indole-2-carboxylates has been developed. © 2006 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 13.
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Hayashi, Hiroyuki ; Ohmoto, Shinobu ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />The first simple total syntheses of 6-cyano-5-methoxy- (1a) and -12-methylindolo[2,3-a]carba
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zolc (1b) are attained from indigo (2) in only five and six steps, respectively. Preparations of 5-hydroxy- (13), 5-bromoindolo[2,3-a]carbazole (14), and a novel spiro compound (7) are also included.
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| 14.
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Kaneko, Chikara ; Fujii, Harue ; Kawai, Shinji ; Hashiba, Kazuhiko ; Karasawa, Yoshio ; Wakai, Masue ; Hayashi, Reiko ; Somei, Masanori
概要:
Irradiation (≥300 nm) of methyl 2-phenyl-3, 1-benzoxazepine-5-carboxylate in an alcohol afforded the Z-isomer of methyl
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3-alkoxy-2-(2-benzamidophenyl)-acrylate as the major addition product. In contrast, thermal reaction of the oxazepine with a primary alcohol in the presence of triethylamine led to the exclusive formation of the corresponding E-isomer. The same kinds of Michael addition products were also obtained stereoselectively from 3, 1-benzoxazepines having an acetyl group at the 5-position under these conditions. The interrelation between the stereoisomers obtained from the oxazepine and an alcohol under these two conditions was established by photochemical equilibration, and the stereochemistry of the two isomers was determined by proton magnetic resonance spectroscopy. An explanation is proposed for the observed stereoselectivities in the two kinds (photochemical and thermal) of reactions.
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| 15.
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Kaneko, Chikara ; Naito, Toshihiko ; Hashiba, Marimi ; Fujii, Harue ; Somei, Masanori
概要:
Two alkaloids, 1-methyl-4-(3-methylbut-2-enyloxy)-2-quinolone (revenine : IIc) and 4-methoxy-1-methyl-2-quinolone (IIa), were synthesized by means of a photochemical rearrangement reaction of the corresponding
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4-alkoxy-2-methylquinoline 1-oxide (Ic and Ia), which were conveniently prepared from 4-chloro-2-methylquinoline 1-oxide (XVII), which in turn is readily obtainable from 2-methylquinoline 1-oxide via the 4-nitrated compound (XVIII). The mechanism of the photo-rearrangement reaction of 4-alkoxy-2-methylquinoline 1-oxides (Ia-d) in methanol is discussed.
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| 16.
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Yamada, Koji ; Tanaka, Yoshio ; Somei, Masanori
概要:
Nb-Acyl- and Nb-acyl-1-hydroxytryptamines are found to be novel and structurally simple (α2-blocker for the treatment of erectile dysfunction. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 17.
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Hayashi, Hiroyuki ; Suzuki, Yoshiaki ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Starting from indigo, simple synthetic methods for 6-cyano-5-methoxy- 12-methyl
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indolo[2,3-a]carbazole and novel 6-aminoindolo[2,3-a]thiazolo-[5,4- c]carbazoles are achieved using only conventional reagents.
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| 18.
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Sato, Masako ; Suzuki, Yoshiaki ; Yamada, Fumio ; Somei, Masanori
概要:
Various derivatives of (6R (*),6aR (*))-6-chloro-6a-hydroxy-5, 6,6a,12-tetrahydroindolo[2,3-a]carbazole-5-one (8) and 6-
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cyano-5- hydroxyindolo[2,3-a]-carbazole (9) are prepared. Preparations of (6R (*),6aR (*),11aR (*))-6-chloro-11a-cyano-6a-hydroxy- (11) and 12-substituted 6-(Z)-aminomethylidene-5,6,6a, 11,11a,12-hexahydroindolo[2,3-a] carbazole-5-ones (15) are also reported. © 2010 The Japan Institute of Heterocyclic Chemistry Received.
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| 19.
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Somei, Masanori ; Yamada, Fumio ; Kato, Jun ; Suzuki, Yoshiaki ; Ueda, Yoshinori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Their Diels-Alder reaction produced 11-alkyl-, 11-allyl-, and 11-β-glycosylindo
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lo[2,3-a]carbazoles. Formation of a novel 6,7-dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine derivative is also reported.
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| 20.
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Iwaki, Takako ; Yamada, Fumio ; Funaki, Shiho ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Three methods have been newly developed for the synthesis of 1,2,3,3a,8,8a-hexa
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hydropyrrolo[2,3-b]indoles. Employing them, 3a-chloro-, 3a-bromo-, 3a-hydroxy-, and various 3a-alkoxy-1,2,3,3a,8,8a-hexahydropyrrolo[2, 3-b]indoles are now readily available.
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| 21.
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Somei, Masanori ; Ohnishi, Hiroyuki
概要:
The first synthesis of (±)-paniculidine B is achieved from 2-nitrotoluene in seven steps with an overall yield of 16%.
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| 22.
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Somei, Masanori ; Nakajou, Masahiro ; Teramoto, Tsuyoshi ; Tanimoto, Asuka ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A simple synthetic route was established for 3-acetyl-1-methoxyindole, which wa
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s found to undergo nucleophilic substitution reactions selectively at the 2-position. Applying the reaction, novel 2-substituted methyl 2,3- dihydro-1-methyl-3-oxo-5H-pyrido[4,3-b]indole-4-carboxylates were prepared.
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| 23.
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Chikara, Kaneko ; Momose, Yu ; Maeda, Tsuyoshi ; Naito, Toshihiko ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 24.
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Yamada, Koji ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />Nucleophiles react with 1-methoxy-3-(2-nitrovinyl)indole (3) at the 2-position regioselectiv
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ely in a dipolar aprotic solvent (DMF or HMPA), while in THF they undergo Michael addition to the β-carbon of nitrovinyl side chain. Depending on bases employed, the resultant Michael addition products (6d, 10, and 11) are found to undergo interesting cyclizations to give novel 3-substituted 1-methoxyindoles (7, 9, and 12).
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| 25.
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Somei, Masanori ; Noguchi, Koichi ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Hydroxyyohimbine was prepared for the first time. Its skeletal rearrangement
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reaction either directly into 2-oxindole or into 3-oxindole derivatives by a series of reaction is reported. 1-Hydroxyyohimbine and some of its derivatives showed potent α2 blocking activity.
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| 26.
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Kawasaki, Toshiya ; Kodama, Atsushi ; Nishida, Tokiko ; Shimizu, Kazuhisa ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 27.
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Somei, Masanori ; Matsubara, Mari ; Natsume, Mitsutaka
概要:
Pyridazino[2, 3-a]indole derivatives, such as (3a-c), (5a), (6a), (10), (12a-b), (13), (14), (19), (20), and (21) were prepared from 1-aminoindoles. as-Triazino[1, 6-a]indole derivatives, such as (17) and (18) were also prepared.
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| 28.
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Nakai, Yu-ya ; Goto, Aya ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Syntheses of N-2-(1-hydroxyindol-3-yl)ethyl-1-hydroxyindole-3-acetamide (3a) an
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d -indole-3-acetamide (4a) are reported. They undergo nucleophilic substitution reaction at the 1-position upon reaction with indole in 85% formic acid to give new type compounds, N-2-[1-(indol-3-yl)indol-3-yl]ethylindole-3-acetamide (13), N-2-(indol-3-yl)ethyl-(14), and N-2-[1-(indol-3-yl)indol-3-yl]ethyl-1-(indol-3-yl)indole-3-acetamide (15).
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| 29.
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Hasegawa, Masakazu ; Nagahama, Yoshiyuki ; Kobayashi, Kensuke ; Hayashi, Masumi ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Formations of 6-mesyloxytryptamines and 1-substituted 3a-(4- chlorobutoxy)-1,2,
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3,3a,8,8a-hexahydropyrrolo[2,3-b]indoles were newly found in the reactions of Nb-substituted 1-hydroxytryptamines with mesyl chloride in THF. The latter compounds suggest that the intermediate indol-3-yl cations can trap THF and cleave the ether bond..
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| 30.
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Yamada, Fumio ; Goto, Aya ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A simple and convenient synthetic methodology for 3a-(indol-3-yl)- 1,2,3,3a,8,8
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a-hexahydropyrrolo[2,3-b]indole, the core structure of leptosins D-F is developed by applying nucleophilic substitution reaction of 1- hydroxytryptamines.
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| 31.
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Somei, Masanori ; Yamada, Fumio ; Izumi, Tomoyuki ; Nakajou, Masahiro
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Methoxy-3-(2-nitrovinyl)indole (4) functions as an electrophile and reacted w
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ith various nucleophiles regioselectively at the 2-position. Employing allyl alkoxides as nucleophiles, a novel synthetic method of pyrrolo[2,3-b]indoles has been elaborated. Utilizing the method, the synthesis of (±)-debromofIustramine B (10b) was achieved.
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| 32.
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Yamada, Koji ; Izumi, Tomoyuki ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Methoxy-3-(2-nitrovinyl)indole (1a) functions as an electrophile and reacts w
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ith various nucleophiles. In THF, nucleophiles undergo conjugate addition to the β-carbon of the nitroviyyl side chain of 1a, regioselectively. The resultant Michael addition products (4d and 8) cyclize to novel 3-substituted 1-methoxyindoles (5 and 7) depending on reaction conditions and a plausible mechanism is discussed. In dipolar aprotic solvent (DMF), nucleophiles react with 1a at the 2-position predominantly with concomitant liberation of the 1-methoxy group giving 2-substituted indoles. © 2005 The Japan Institute of Heterocyclic Chemistry.
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| 33.
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Yamada, Koji ; Tanaka, Yoshio ; Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />Nb-Acyl- and Nb-acyl-1-hydroxytryptamines are found to be novel and structurally simpl
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e (α2-blocker for the treatment of erectile dysfunction. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 34.
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Somei, Masanori ; Yamada, Fumio ; Yamamura, Gaku
概要:
A simple synthetic method for 5H-pyrido[4, 3-b]indole (γ-carboline) derivatives having a methoxycarbonyl group at the 4-
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position was developed based on 1-hydroxyindole chemistry. By applying the method, various 3-substituted metyl 5H-pyrido[4, 3-b]indole-4-carboxylates and 2-substituted methyl 2, 3-dihydro-3-oxo-5H-pyrido[4, 3-b]indole-4-carboxylates were prepared.
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| 35.
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Somei, Masanori ; Kawasaki, Toshiya ; Ohta, Toshiharu
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 36.
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Somei, Masanori ; Sayama, Shinsuke ; Naka, Katsumi ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 37.
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Somei, Masanori ; Sato, Haruhiko ; Komura, Naoko ; Kaneko, Chikara
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 38.
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Somei, Masanori ; Funamoto, Tetsuo ; Ohta, Toshiharu
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 39.
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Somei, Masanori ; Noguchi, Koichi ; Yoshino, Katsumasa ; Mori, Koichiro ; Asada, Mamiko ; Yamada, Fumio ; Tanaka, Yoshio ; Shigenobu, Koki ; Koike, Katsuo
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 40.
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Somei, Masanori ; Kawasaki, Toshiya
概要:
The first total synthesis of bipolaramide was achieved in 47% overall yield from (2S__-)-2, 3-dihydroindole-2-carboxylic acid in three steps, utilizing thallium chemistry. Some derivatives, with dihalogeno or dialkenyl substituents at the 4
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and 11 positions of (6aS__--cis)-6a, 7, 13a, 14-tetrahydropyrazino[1, 2-a : 4, 5-a']diindole-6, 13-dione have also prepared
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| 41.
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Somei, Masanori ; Iwaki, Takako ; Yamada, Fumio ; Tanaka, Yoshio ; Shigenobu, Koki ; Koike, Katsuo ; Suzuki, Nobuo ; Hattori, Atsuhiko
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />According to the definition of the ideal synthetic method, an example aimed at
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the leads for an α2 blocker, an inhibitor of platelet aggregation, and an anti-osteoporosis agent is established starting from tryptamine. The originality rate, the intellectual property, and the application potential factors of the method are 71, 54, and 100, respectively. The method employs only conventional reagents and reaction conditions without using any protecting groups.{A figure is presented}. © 2006 The Japan Institute of Heterocyclic Chemistry
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| 42.
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Somei, Masanori ; Noguchi, Koichi ; Yamagami, Ryutaro ; Kawada, Yumiko ; Yamada, Koji ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Novel 9-hydroxy-β-carboline derivatives were produced for the first time. A nov
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el rearrangement reaction of 1, 2, 3, 4-tetrahydro-9-hydroxy-β-carbolines was discovered to give 3, 3-disubstituted oxindoles, which was successfully applied to the total synthesis of (±)-coerulescine.
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| 43.
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Somei, Masanori ; Yamada, Fumio ; Suzuki, Yoshiaki ; Ohmoto, Shinobu ; Hayashi, Hiroyuki
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />For evaluating the effectiveness of organic synthesis, both intellectual property factor (IP
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F) and application potential factor (APF) are proposed. As a representative example, a highly effective synthetic method with IPF value of 53.8 and APF value of 100 has been established starting from indigo directing toward an antibiotic, 6-cyano-5-methoxy-12-methylindolo[2,3-a]carbazole, using only conventional reagents without using any protecting groups. © 2004 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 44.
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Somei, Masanori ; Oshikiri, Naoki ; Hasegawa, Masakazu ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A unique synthetic method for melatonin was established through biologically pr
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omising synthetic intermediates. 1-Hydroxymelatonin was prepared as crystals for the first time. It reacted with 85% formic acid to give (±)-3a,3a'-bispyrrolo[2,3-b]indole compound, whose structure was unequivocally determined by X-Ray crystallographic analysis
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| 45.
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Somei, Masanori ; Saida, Yoshihiro ; Funamoto, Tetsuo ; Ohta, Toshiharu
概要:
A simple four-step synthetic method for 7-iodo-, 7-bromo-and 7-chloroindole was established with high overall yield starting from 2, 3-dihydroindole. Several 7-substituted indoles carrying a carbon side chain and 7-methoxyindole were also
…
synthesized.
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| 46.
論文 |
論文
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Somei, Masanori ; Kawasaki, Toshiya
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />The first and simple total synthesis of bipolaramide was achieved in 31 % overa
…
ll yield from (2S)-2,3-dihydroindole-2-carboxylic acid in three (or two) steps. Derivatives of bipolaramide having halogen, alkenyl, nitro, or azido substitueras were also prepared.
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| 47.
論文 |
論文
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Kaneko, Chikara ; Naito, Toshihiko ; Momose, Yu ; Shimomura, Naoyuki ; Ohashi, Tetsuo ; Somei, Masanori
概要:
Cyclopentane ring annelation methods for 2-pyridone derivatives are provided by cyclobutane ring expansion of 1, 2-dihydrocyclobuta [c] pyridin-3 (4H)-ones having an appropriate function at the l-position. Since the latter compounds are
…
readily accessible from 4-alkoxy-2-pyridones via our two-step procedure (Kaneko-Naito method), the methods seem to have wide applicability for the synthesis of cyclopenta [c] pyridines.
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| 48.
論文 |
論文
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Somei, Masanori ; Karasawa, Yoshio ; Shoda, Toshiya ; Kaneko, Chikara
概要:
A convenient synthesis of 5-substituted isocoumarin derivatives, such as 5-nitroisocoumarin (2), 5-aminoisocoumarin (8), 3, 4-dihydro-3-methoxy-5-nitroisocoumarin (3), and 5-amino-3,
…
4-dihydro-3-methoxyisocoumarin (10), from 2-methyl-3-nitrobenzoic acid (1) is reported. Several synthetic routes to methyl indole-4-carboxylate (9) from methyl 2-methyl-3-nitrobenzoate (4) directly or via these isocoumarins (8 and 10) are also presented.
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| 49.
論文 |
論文
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Yoshino, Katsumasa ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />X-Ray analyses of 1-hydroxyyohimbine derivatives clearly show the deviation of the N(1
…
)-O bond from the indole molecular plane. This phenomenon supports our working hypothesis "bishomoallylic conjugation". The deviation is responsible for the unprecedented nucleophilic substitution reaction in 1-hydroxyindole chemistry and effected the synthesis of novel 7β-heteroarylyohimbine and 4aα-heteroaryl-1,2,3,4-tetrahydro-β-carboline derivatives from the corresponding 1-hydroxyindole derivatives. © 2008 The Japan Institute of Heterocyclic Chemistry All rights reserved.
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| 50.
論文 |
論文
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Yamada, Fumio ; Shinmyo, Daisuke ; Nakajou, Masahiro ; Somei, Masanori
概要:
1-Methoxyindole-3-carbaldehyde is proved to be a versatile electrophile and reacts regioselectively at the 2-position wi
…
th various types of nucleophiles providing 2-substituted indole-3-carbaldehydes. © 2012 The Japan Institute of Heterocyclic Chemistry.
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| 51.
論文 |
論文
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Suzuki, Nobuo ; Somei, Masanori ; Kitamura, Keiichiro ; Reiter, Russel J. ; Hattori, Atsuhiko
概要:
金沢大学環日本海域環境研究センター生物多様性研究部門<br />The teleost scale is a calcified tissue that contains osteoclasts, osteoblasts, and bone
…
matrix, all of which are similar to those found in mammalian membrane bone. Using the goldfish scale, we recently developed a new in vitro assay system and previously demonstrated that melatonin suppressed both osteoclastic and osteoblastic activities in this assay system. In mammals, 2-bromomelatonin possesses a higher affinity for the melatonin receptor than does melatonin. Using a newly developed synthetic method, we synthesized 2-bromomelatonin, 2,4,6-tribromomelatonin and novel bromomelatonin derivatives (1-allyl-2,4,6-tribromomelatonin, 1-propargyl-2,4,6-tribromomelatonin, 1-benzyl-2,4,6-tribromomelatonin, and 2,4,6,7-tetrabromomelatonin) and then examined the effects of these chemicals on osteoclasts and osteoblasts. All bromomelatonin derivatives, as well as melatonin, had an inhibitory action on osteoclasts. In particular, 1-benzyl-2,4,6-tribromomelatonin (benzyl-tribromomelatonin) possessed a stronger activity than melatonin. At an in vitro concentration of 10-10 m, benzyl-tribromomelatonin still suppressed osteoclastic activity after 6 hr of incubation. In reference to osteoblasts, all bromomelatonin derivatives had a stimulatory action, although melatonin inhibited osteoblastic activity. In addition, estrogen receptor mRNA expression (an osteoblastic marker) was increased in benzyl-tribromomelatonin (10-7 m)-treated scales. Taken together, the present results strongly suggest that these novel melatonin derivatives have significant potential for use as beneficial drug for bone diseases such as osteoporosis. © 2007 The Authors. 全文公開200904
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| 52.
論文 |
論文
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Ohta, Toshiharu ; Yamato, Yoshinori ; Tahira, Hiroko ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 53.
論文 |
論文
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Yamada, Fumio ; Saida, Yoshihiro ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 54.
論文 |
論文
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Yamada, Fumio ; Kobayashi, Kensuke ; Shimizu, Aya ; Aoki, Naokatsu ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 55.
論文 |
論文
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Yamada, Fumio ; Fukui, Yoshikazu ; Shinmyo, Daisuke ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 56.
論文 |
論文
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Hamabuchi, Shin ; Hamada, Hirokazu ; Hironaka, Akiko ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 57.
論文 |
論文
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Somei, Masanori ; Ohnishi, Hiroyuki ; Shoken, Yuka
概要:
The first syntheses of 1-methoxy analogs of ergot alkaloids, (±)-1-methoxy-6, 7-secoagroclavine and (±)1-methoxy-6-nor-6, 7-secoagroclavine, were achieved with good overall yield in only nine steps from 2-nitrotoluene.
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| 58.
論文 |
論文
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Yamada, Koji ; Yamada, Fumio ; Shiraishi, Takei ; Tomioka, Saori ; Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授
|
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| 59.
論文 |
論文
|
Hayashi, Toshikatsu ; Nakai, Yu-ya ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A novel synthetic method is discovered for 3-hydroxy-3H-indole-3-ethanamines an
…
d -3H-indole-3-acetamides having either a 4-morpholinyl or 1-pyrrolidinyl group at the 2-position by reacting the corresponding 1-hydroxyindoles with enamines in the presence of tosyl or mesyl chloride. A plausible mechanism is proposed.
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| 60.
論文 |
論文
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Somei, Masanori ; Kawasaki, Toshiya ; Shimizu, Kazuhisa ; Fukui, Yoshikazu ; Ohta, Toshiharu
概要:
Methyl 1-hydroxyindole-3-acetate, (±)-2-acetoamino-3-(10hydroxyindol-3-yl)propanol, N__-b-acetyl-1-hydroxytryptamine, (±
…
)- and (S__-)-(+)-N__-b-acetyl-1-hydroxytryptophan methyl ester, which are needed for inspecting our hypothesis regarding the metabolism of tryptophan, were prepared for the first time. The structural proof of (±)-N__-b-acetyl-1-hydroxytryptophan methyl ester by X-ray crysatllographic analysis is also reported.
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| 61.
論文 |
論文
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Kaneko, Chikara ; Fujii, Harue ; Kawai, Shinji ; Yamamoto, Atsushi ; Hashiba, Kazuhiko ; Kimata, Toshihiko ; Hayashi, Reiko ; Somei, Masanori
概要:
A novel photochemical ring-contraction reaction of 5-unsubstituted 3, 1-benzoxazepines and their 5-halogeno or carboxyl
…
derivatives to yield 3-formylindoles in an aprotic solvent is reported. This ring contraction was successfully extended to oxazepines having an alkoxycarbonyl function at the 5-position to give the indoles having this function at the 3-position. Though most of the oxazepines underwent the ring-contraction reaction only on irradiation at 254 nm, 5-carboxy derivatives or their esters afforded the ring-contraction products even at ≥ 300 nm. The intermediacy of 3H-indole species in these photochemical ring-contraction reactions was demonstrated by the isolation of methyl 3-acetyl-2-phenyl-3H-indole-3-carboxylate during the photolysis of methyl 4-methyl-2-phenyl-3, 1-benzoxazepine-5-carboxylate. It was found that this 3H-indole afforded methyl 6-and 4-acetyl-2-phenyl-indole-3-carboxylates upon further irradiation. The mechanism of this acetyl migration is discussed based on the result of the photochemical acetyl migration of methyl 1-acetyl-2-phenylindole-3-carboxylate.
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| 62.
論文 |
論文
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Somei, Masanori ; Yamada, Yoshikazu ; Kitagawa, Keiichi ; Sugaya, Katsuko ; Tomita, Yayoi ; Yamada, Fumio ; Nakagawa, Kyoko
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />2-Amino-4-(1-methylindol-3-yl)thiazole (11c) has a characteristic nucleophilic
…
nature at the 5-position and add to the 4-position of acetylpyridinium acetate (13) producing 2-acetylamino-5-(1-acetyl-1,4-dihydropyridin-4-yl)-4-(1-methylindol-3-yl) thiazole (1c). Its structure was established by X-ray single crystallographic analysis. Applying the results, simple syntheses of the related tris- (1a-b and 2-8) and tetrakis-linked heterocycles (9) were achieved.
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| 63.
論文 |
論文
|
Iwaki, Takako ; Fujita, Yasuaki ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-(β-D-Xylopyranosyl)- (2a), 1-(β-D-glucopyranosyl)- (2b), 1-(β-D-galactopyrano
…
syl)- (2c), and 1-(α-D-arabinopyranosyl)melatonins (3b) are prepared as water-soluble melatonins starting from melatonin.
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| 64.
論文 |
論文
|
Yamada, Koji ; Kawasaki, Toshiya ; Fujita, Tomomi ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Nucleophilic substitution reaction of 1-methoxy-6-nitroindole (1) was examined.
…
In the reaction with sodium methoxide or sodium cyanide as a nucleophile, 2- and 3-methoxy-6-nitroindoles, and 7-cyano-6-nitroindole were obtained, respectively. A novel methylene homologation at the 3-position was found in the reaction of 1 with sodium methyl sulfide or potassium salt of diethyl malonate to give 3-methylthiomethytyl-6-nitroindole and its 2-methylthio derivative, and diethyl 2-(6-nitroindol-3-yl)methylmalonate, respectively. Possible reaction mechanism is discussed.
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| 65.
論文 |
論文
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Yamada, Koji ; Teranishi, Sakiko ; Miyashita, Ayako ; Ishikura, Minoru ; Somei, Masanori
概要:
Utilizing novel Nb-substituted serotonins, 5-and/or 6-substituted 3,4,5,6-tetrahydro-7-hydroxy-1H-azepino[5,4,3-cd]indol
…
e derivatives are produced simply by treating serotonins with aldehydes under basic conditions. Synthesis of 2,2a,3,4,5,6-hexahydro-7-hydroxy-1H-azepino[5,4,3-cd]indole-2-one derivatives is also reported. © 2011 The Japan Institute of Heterocyclic Chemistry.
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| 66.
論文 |
論文
|
Suzuki, Nobuo ; Somei, Masanori ; Seki, Azusa ; Reiter, Russel J. ; Hattori, Atsuhiko
概要:
金沢大学環日本海域環境研究センター生物多様性研究部門<br />Several reports indicate that melatonin is involved in the regulation of bone metabolism
…
. To examine the direct effect of melatonin on osteoclasts and osteoblasts, we developed an in vitro assay using fish scales that contain osteoclasts, osteoblasts, and bone matrix, all of which are similar to those found in mammalian membrane bone. Using the assay, we demonstrated that melatonin suppressed osteoclastic and osteoblastic activities. These findings are in agreement with the reports from in vivo studies in mice and rats. In an attempt to develop molecules that increase bone mass, novel bromomelatonin derivatives were synthesized, and the effects of these chemicals on osteoclasts and osteoblasts using the scale assay were examined. As a result, novel bromomelatonin derivatives with the ability to possibly increase bone formation were identified. In scale osteoclasts, particularly, 1-benzyl-2,4,6- tribromomelatonin had a more potent activity than melatonin. In reference to osteoblasts, this agent (10-9-10-6m) significantly activated osteoblasts. The effect of 1-benzyl-2,4,6-tribromomelatonin on bone formation was confirmed in ovariectomized rats. Thus, the oral administration of 1-benzyl-2,4,6-tribromomelatonin augmented the total bone mineral density of the femoral metaphysis of ovariectomized rats. The stress-strain index of the diaphysis in 1-benzyl-2,4,6-tribromomelatonin-treated rats significantly increased in comparison with that in ovariectomized rats. In rats fed a low-calcium diet, the total bone mineral density of the femoral metaphysis significantly increased following the oral administration of 1-benzyl-2,4,6-tribromomelatonin. These studies identified a melatonin derivative that may have potential use in the treatment of bone diseases, such as osteoporosis. © 2008 The Authors.
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| 67.
論文 |
論文
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Somei, Masanori ; Makita, Yoshihiko ; Yamada, Fumio
概要:
The simple total synthesis of the ergot alkaloids, (±)-norchanoclavine-I, (±)-chanoclavine-I, (±)-isochanoclavine-I, and
…
(±)-agroclavine was achieved by a practical and common synthesis method. A new regio-selective oxidation of the Z-methyl group of the isoprenyl system with selenium dioxide is described.
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| 68.
論文 |
論文
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Somei, Masanori ; Yamada, Fumio
概要:
A novel reductive amino-cyclization method for the synthesis of azacycloalkanes is developed. Its versatility is proved
…
by the total syntheses of (±)-aurantioclavine (1), an ergot alkaloid, and (±)-lophocerine (2), a cactus alkaloid, as examples of azepane and piperidine skeletons, respectively. © 2007 The Japan Institute of Heterocyclic Chemistry.
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| 69.
論文 |
論文
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Yamada, Koji ; Yamada, Fumio ; Shiraishi, Takei ; Tomioka, Saori ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Methoxy-6-nitroindole-3-carbaldehyde is proved to be a versatile substrate fo
…
r the nucleophilic substitution reactions providing 2,3,6-trisubstituted indole derivatives. Preparation of a novel pyrimido[1,2-a]indole derivative is also reported.
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| 70.
論文 |
論文
|
Somei, Masanori ; Inoue, Satomi ; Tokutake, Shoichi ; Yamada, Fumio ; Kaneko, Chikara
概要:
Various 1-hydroxyindoles carrying a nitro, methoxycarbonyl, or benzyloxy group at the 4 position were prepared by the co
…
ntrolled reduction of 6-substituted trans-β-dimethylamino-2-nitrostyrenes with either aqueous titanium (III) chloride or zinc in aqueous ammonium chloride. The stability of 4-substituted 1-hydroxyindoles decreased in the following order : 4-nitro-»4-methoxycarbonyl->4-benzyloxy-1-hydroxyindole. This result clearly indicates that an electron-withdrawing group at the 4-position can stabilize the 1-hydroxyindole structure. It was also found that 4-hydroxy-and 4-benzyloxy-indole were readily accessible by the reduction of 6-benzyloxy-2-nitrophenyl acetaldehyde. A unique route to 4-or 7-aminoindole from cinnoline is also described.
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| 71.
論文 |
論文
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Somei, Masanori ; Sayama, Shinsuke ; Naka, Katsumi ; Shinmoto, Kotaro ; Yamada, Fumio
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />Abstract - Various new 2-substituted indole-3-carbaldehydes are prepared. Structurally
…
related alkaloids, vulcanine and borreline, are synthesized as well. Among the compounds, 2-haloindole-3-carbaldehydes are found to be potent promoters of plant's root growth. Its successful preliminary application is reported for making Gobi desert in Inner Mongolia full of plant. © 2007 The Japan Institute of Heterocyclic Chemistry.
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| 72.
論文 |
論文
|
Yamada, Koji ; Yamada, Fumio ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />1-Hydroxytryptamine derivatives undergo nucleophilic substitution reaction on the indole nit
…
rogen (Na) as a general reaction by the treatment with acid, providing a novel synthetic method for 1-aryltryptamines. Depending on the structures of nucleophiles, 5- and 7-substituted tryptamines can also be produced in addition to the 1-aryltryptamines.<br />An easy approach to 7-substituted 4,5-dihydro-7H-pyrano[3,4-c]-isoxazole derivatives (3a-b and 6a-d) is described by the reaction of 2-aryl substituted 1-nitro-3-oxa-6-heptynes (2, 5a and 5b) with n-BuLi, followed by treatment with acetic anhydride.
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| 73.
論文 |
論文
|
Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />This review summarizes our hypotheses, syntheses, physical and chemical propert
…
ies, and chemical reactions of 1-hydroxyindoles. Syntheses of natural products having 1-methoxyindole nucleus and 1-methoxy derivatives of indole alkaloids are also included. Application of the chemistry of 1-hydroxyindoles to the syntheses of biologically active substances, syntheses of tryptophan- 4,5-diones and their reactions, and biological evaluation of 1-hydroxyindoles are reviewed.
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| 74.
論文 |
論文
|
Somei, Masanori ; Hamamoto, Shoichi ; Nakagawa, Kyoko ; Yamada, Fumio ; Ohta, Toshiharu
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部
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| 75.
論文 |
論文
|
Somei, Masanori ; Tokutake, Shoichi ; Kaneko, Chikara
概要:
The first syntheses of 6, 6a, 7, 8, 9, 9a-hexahydro-and 6, 6a, 9, 9a-tetrahydro-2H-isoindolo [4, 5, 6-cd] indoles are described. The preparation of 1, 3, 4, 5-tetrahydrobenz [cd] indole derivatives is also included.
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| 76.
論文 |
論文
|
Somei, Masanori
概要:
Various derivatives of indole-3-carbaldehyde are found to be root regulators and they are named SOMRE compounds. Since s
…
ome of them are potent root promoters and make roots three times longer than usual, their possibilities for increasing food production, combating yellow sand and desertification in Gobi desert, China, were examined. All preliminary experiments are thus far working well. For greening desert and stopping the global warming, it is vital importance to sow seeds to vast area of sand dune all at once. We are now on the stage to scatter seeds, pretreated with SOMRE, to sand dune by airplane. © The Japan Institute of Heterocyclic Chemistry.
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| 77.
論文 |
論文
|
Somei, Masanori ; Yamada, Fumio ; Kurauchi, Takashi ; Nagahama, Yoshiyuki ; Hasegawa, Masakazu ; Yamada, Koji ; Teranishi, Sakiko ; Sato, Haruhiko ; Kaneko, Chikara
概要:
Application of regioselective nucleophilic substitution reactions of 1-hydroxytryptamines to novel and simple syntheses of serotonin (1a), N-methylserotonin (1b), bufotenine (1c), 5-methoxy-N-methyltryptamine (2a),
…
bufobutanoic acid (3a), N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine (4), and lespedamine (5) are described. Effective syntheses of 5-benzyloxytryptamine and 1-methoxy-2-oxindoles are also reported.
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| 78.
論文 |
論文
|
Yamada, Fumio ; Goto, Aya ; Peng, Wu ; Hayashi, Toshikatsu ; Saga, Yoshitomo ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A novel nucleophilic substitution reaction at the 1-position of indole nucleus
…
was discovered by reacting 1-hydroxytryptamine and -tryptophan derivatives with indoles in 85% formic acid yielding 1-(indol-3-yl)indoles. Their structures were determined by X-Ray crystallographic analysis and chemical correlations. An SN2 mechanism on the indole nitrogen (1-position) is proposed.
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|
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| 79.
論文 |
論文
|
Yamada, Koji ; Kanbayashi, Yukiko ; Tomioka, Saori ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Syntheses of wasabi phytoalexin analogs, such as 6-bromo-5-iodo, 2-bromo-5-iodo
…
, 6-nitro, 5-chloroacetyl, and 6-chloroacetyl congeners, are reported. An interesting effect of the 1-methoxy group on the regioselectivity of electrophilic substitution reactions on indole nucleus is observed.
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| 80.
論文 |
論文
|
Somei, Masanori ; Tanimoto, Asuka ; Orita, Hitomi ; Yamada, Fumio ; Ohta, Toshiharu
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A simple synthetic method for methyl 1-methoxyindole-3-carboxylate, a phytoalex
…
in isolated from Wasabia japonica, syn. Eutrema wasabi, and its 5-iodo derivative is reported. They underwent nucleophilic substitution reactions selectively at the 2-position.
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|
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| 81.
論文 |
論文
|
Somei, Masanori ; Morikawa, Harunobu ; Yamada, Koji ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-Hydroxytryptamines (6a-f) having (E)-3-phenyl-, (E)-3-(4-hydroxyphenyl)-, (E)
…
-3-(4-hydroxy-3-methoxyphenyl)propenoyl, octanoyl, hexadecanoyl, and docosanoyl group as a Nb-substituent are prepared for the first time. Preparations of serotonins (2a-c, e) from the corresponding 1-hydroxytryptamines (6a-c, e) are also reported. A novel homologation on the 3-substituent of 1-hydroxytryptamines is discovered upon treatment with diazomethane in chloroform or dichloromethane.
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|
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| 82.
論文 |
論文
|
Yamada, Fumio ; Hayashi, Toshikatsu ; Yamada, Koji ; Somei, Masanori
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A lithium hydroxide promoted glucosidation of 1-hydroxyindoles with 2, 3, 4, 6-
…
tetra-0-acetyl-α-D-glucopyranosyl bromide is newly developed. Applying this method, the first and simple syntheses of novel indol-1-yl glucosides were achieved.
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|
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| 83.
論文 |
論文
|
Somei, Masanori ; Yamada, Fumio
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />A lithium hydroxide promoted simple glycosylation of 4-hydroxyindole-3- acetoni
…
trile with 2,3,4, 6-tetra-O-acetyl-a-D-glucopyranosyl bromide was developed. Utilizing the method, the first and five steps total synthesis of cappariloside A was achieved from indole-3-carbaldehyde in 41% overall yield.
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| 84.
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Somei, Masanori ; Yamada, Fumio ; Hayashi, Toshikatsu ; Goto, Aya ; Saga, Yoshitomo
概要:
金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />1-(Indol-3-yl)indoles are obtained in excellent to good yields by the reaction
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of 1-hydroxyindoles with indole in 85% formic acid. Their structures are determined by X-Ray crystallographic analysis and chemical correlations. The unprecidented SN2 mechanism on the indole nitrogen is proposed.
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| 85.
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Yamada, Fumio ; Yamada, Koji ; Takeda, Hikari ; Somei, Masanori
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金沢大学大学院自然科学研究科生理活性物質科学<br />金沢大学薬学部<br />Preparations of 5-nitroindol-1-yl (5a), 6-nitroindol-1-yl (5b), and 1,2,3-benzo
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triazol-1-yl 1-methoxyindole-3-carboxylates (9) are reported. These are active esters and proved to be useful intermediates for the preparations of ester and amide analogs of methyl 1-methoxyindole-3-carboxylate, a wasabi phytoalexin.
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| 86.
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Yamada, Fumio ; Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />A novel reductive amino-cyclization method for the synthesis of azacycloalkanes is dev
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eloped. Its versatility is proved by the total syntheses of (±)-aurantioclavine (1), an ergot alkaloid, and (±)-lophocerine (2), a cactus alkaloid, as examples of azepane and piperidine skeletons, respectively. © 2007 The Japan Institute of Heterocyclic Chemistry.
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| 87.
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Somei, Masanori
概要:
金沢大学医薬保健研究域薬学系<br />金沢大学名誉教授<br />This review reports how the author has been realizing his synthetic philosophy and fiv
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e dreams as his life work. The philosophy consists of such three elements as originality rate, intellectual property factor, and application potential factor. On the basis of these elements, an ideal and an efficient synthesis are defined. In the study for the total synthesis of ergot alkaloids, the first concrete example of an approximately ideal synthesis was demonstrated. Further examples are shown relying on the chemistry of 1-hydroxyindoles. A lot of intellectual properties created by the author are successfully condensed to provide promising lead compounds meeting for the respective dreams of developing five drugs 1) for making desert green and food increase in production, 2) for cardiovascular system disease, 3) for dementia, 4) for lifestyle-related disease (osteoporosis, etc.), and 5) for cancer and virus. With potent promoters of plant's root growth in hand, the first dream is going now successfully. Preliminary experiments combating desertification at Gobi desert in Inner Mongolia are reported in detail, aiming for preventing global warming. © 2008 The Japan Institute of Heterocyclic Chemistry.
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