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Hoshikawa, Takaya ; Tanji, Kei ; Matsuo, Jun-ichi ; Ishibashi, Hiroyuki
概要:
Intramolecular [2+2] cycloaddition of γ,δ-unsaturated ketenes derived from hex-5-enoyl chloride derivatives gave bicyclo[2.1.1]hexan-5-ones with complete regioselectivity. © 2012 The Pharmaceutical Society of Japan.
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| 2.
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Nakano, Takeo ; Soeta, Takahiro ; Endo, Kohei ; Inomata, Katsuhiko ; Ukaji, Yutaka
概要:
The sequential 1,4-elimination reaction of (E)-4-alkoxy-2-butenyl benzoates and [1,2]-Wittig rearrangement gave (2Z,4E)-
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2,4-pentadien-1-ols stereoselectively. Z-Selective formation of intermediary vinyl ethers, whose stereochemistry was well elucidated by the "syn-effect", was achieved by treatment of the 2-butenyl benzoates with KOH in the presence of Pd catalyst. The subsequent [1,2]-Wittg rearrangement by use of n-BuLi proceeded with retention of the stereochemistry of the intermediary vinyl ethers. © 2013 American Chemical Society.
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| 3.
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Higuchi, Akihiro ; Erina Oonishi ; Kawakita, Tetsuya ; Tsubota, Kazuo ; 樋口, 明弘
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金沢大学先端科学・社会共創推進機構<br />Purpose: 2-hydroxy estradiol (2-OHE2) is a catechol derivative of 17β -Estradiol (E2) and it is s
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ynthesized from E2 catalyzed by cytochrome P4501A1. Previous studies reported that 2-OHE2 is a physiologic antioxidant in lipoproteins, liver microsomes, and the brain. Catechol derivatives show an anti-inflammatory effect through the inhibition of prostaglandin endoperoxide synthase (PGS) activity. Corneal erosion caused by dry eye is related to an increase in oxidative stress and inflammation in ocular surface cells. We investigated the therapeutic effects of 2-OHE2 on corneal damage caused by dry eye. Methods: Steroidal radical scavenging activity was confirmed through the electron spin resonance (ESR) method. PGS activity was measured using the COX Fluorescent Activity Assay Kit. To evaluate the effect of 2-OHE2 on the treatment for dry eye, 2-OHE2 was applied as an eye drop experiment using dry eye model rats. Results: 2-OHE2 scavenged tyrosyl radical and possibly suppressed oxidative stress in corneal epithelial cells. In addition, 2-OHE2 inhibited PGS activity, and 2-OHE2 is probably a competitive inhibitor of PGS. Corneal PGS activity was upregulated in the dry eye group. Therefore, 2-OHE2 eye drops improved corneal erosion in dry eye model rats. Conclusions: 2-OHE2 is a candidate for the treatment of dry eye through the suppression of inflammation and oxidative stress in the cornea. © 2016 Molecular Vision.
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| 4.
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Nakata, Shunji ; Kato, Takashi ; Ozaki, Shinya ; Kawae, Takeshi ; Morimoto, Akiharu
概要:
Thin film Al2O3/Al-rich Al2O 3/SiO2 structures were fabricated on p-Si substrates. Radio-frequency magnetron co-sputteri
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ng was used to form Al-rich Al 2O3 thin film as the charge-trapping layer of nonvolatile Al2O3 memory. Capacitance-voltage measurements showed a large hysteresis due to charge trapping in the Al-rich Al2O 3 layer. The charge trap density was estimated to be 42.7 × 1018 cm- 3, which is the largest value ever reported for an Al-rich Al2O3 layer; it is six times larger than that of a conventional metal-nitride-oxide-silicon memory. Thermal annealing was found to reduce the leakage current of the Al2O3 blocking layer, thereby providing this structure with better data retention at room temperature than an as-deposited one. In addition, the annealed structure was found to exhibit good data retention even at 100 C. © 2013 Elsevier B.V. All rights reserved.
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| 5.
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Matsuo, Jun-ichi ; Okuno, Ryosuke ; Takeuchi, Kosuke ; Kawano, Mizuki ; Ishibashi, Hiroyuki
概要:
金沢大学医薬保健研究域薬学系<br />Optimized reaction conditions for the preparation of various 2-monosubstituted 3-ethoxycyclobutanone
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s are described. 2-Monoalkyl 3-ethoxycyclobutanones were efficiently prepared by the reaction of the corresponding carboxylic acid chlorides and an excess amount of ethyl vinyl ether in the presence of diisopropylethylamine at 90 °C in a sealed tube. 2-Monoaryl 3-ethoxycyclobutanones were prepared by using 2,6-lutidine as a base in the above-mentioned procedure. © 2010 Published by Elsevier Ltd. All rights reserved.
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| 6.
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Matsuo, Junichi ; Okuno, Ryosuke ; Takeuchi, Kosuke ; Kawano, Mizuki ; Ishibashi, Hiroyuki
概要:
金沢大学医薬保健研究域薬学系<br />Optimized reaction conditions for the preparation of various 2-monosubstituted 3-ethoxycyclobutanone
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s are described. 2-Monoalkyl 3-ethoxycyclobutanones were efficiently prepared by the reaction of the corresponding carboxylic acid chlorides and an excess amount of ethyl vinyl ether in the presence of diisopropylethylamine at 90 °C in a sealed tube. 2-Monoaryl 3-ethoxycyclobutanones were prepared by using 2,6-lutidine as a base in the above-mentioned procedure. © 2010 Elsevier Ltd. All rights reserved.
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| 7.
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Okado, Ryohei ; Nowaki, Aya ; Matsuo, Jun-ichi ; Ishibashi, Hiroyuki
概要:
A catalytic amount of tin(IV) chloride catalyzed formal [4+2] cycloaddition reaction of di-tert-butyl 2-ethoxycyclobutane-1,1-carboxylate with ketones or aldehydes to give diethyl 6-ethoxydihydro-2H-pyran-3,3(4H)-dicarboxylates,
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whereas two equivalents of trimethylsilyl triflate promoted tandem [4+2] cycloaddition and lactonization to afford 3-oxo-2,6-dioxabicyclo[2.2.2]octane-4-carboxylate esters.
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| 8.
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Yokota, Shinichi ; Higashi, Eriko ; Fukami, Tatsuki ; Yokoi, Tsuyoshi ; Nakajima, Miki
概要:
金沢大学医薬保健研究域薬学系<br />Human CYP2A6 is responsible for the metabolism of nicotine and coumarin as well as the metabolic act
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ivation of tobacco-related nitrosamines. Earlier studies revealed that CYP2A6 activity was increased by dietary cadmium or cruciferous vegetables, but the underlying mechanisms remain to be clarified. In the present study, we investigated the possibility that Nrf2 might be involved in the regulation of CYP2A6. Real-time RT-PCR analysis revealed that the CYP2A6 mRNA level in human hepatocytes was significantly (P < 0.01, 1.4-fold) induced by 10 μM sulforaphane (SFN), a typical activator of Nrf2. A computer-based search identified three putative antioxidant response elements (AREs) in the 5′-flanking region of the CYP2A6 gene at positions -1212, -2444, and -3441, termed ARE1, ARE2, and ARE3, respectively. Electrophoretic mobility shift assays demonstrated that Nrf2 bound only to ARE1. Luciferase assays using HepG2 cells revealed that the overexpression of Nrf2 significantly increased the reporter activities of the constructs containing a 30-bp fragment that included ARE1. However, the activity of the construct containing the intact 5′-flanking region (-1 to -1395) including ARE1 was not increased by the overexpression of Nrf2. In contrast, when the reporter construct was injected into mice via the tail vein, the reporter activity in the liver was significantly (P < 0.05, 1.9-fold) increased by SFN (1 mg/head) administration. In conclusion, we found that human CYP2A6 is regulated via Nrf2, suggesting that CYP2A6 is induced under oxidative stress. © 2010 Elsevier Inc. All rights reserved.
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| 10.
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Miyamoto, Yoshiaki ; Wada, Norihiro ; Soeta, Takahiro ; Fujinami, Shuhei ; Inomata, Katsuhiko ; Ukaji, Yutaka
概要:
The stereoselective direct transformation of N-(propargylic)hydroxylamines into cis-2-acylaziridines was achieved by the
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combined use of AgBF4 and CuCl. Copper salts were found to promote the transformation of the intermediary 4-isoxazolines into 2-acylaziridines and both 3-aryl- and 3-alkyl-substituted 2-acylaziridines could be prepared by using this method. Furthermore, subsequent 1,3-dipolar cycloaddition of azomethine ylides that were generated in situ from the intermediary 2-acylaziridines with maleimides was achieved in a stereoselective one-pot procedure to afford the corresponding 2-acylpyrrolidines, which consisted of an octahydropyrrolo[3,4-c]pyrrole skeleton. Love the way ylide: The transformation of N-(propargylic) hydroxylamines into cis-2-acylaziridines and subsequent 1,3-dipolar cycloaddition of the in situ generated azomethine ylides with maleimides stereoselectively afforded 2-acylpyrrolidines. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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