Studies on the Mechanism of 1,2-Dihydropyrazin-2-one Ring Formation from Dipeptidyl Chloromethyl Ketone and Its Chemical Properties : Immediate Deamination during Catalytic Hydrogenation

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概要

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• 1,2-Dihydropyrazin-2-one derivatives, which have two aminoalkyl groups at the positions 3 and 6, were found to be efficient tools for the construction of potent, selective and long-acting opioid mimetics. During the course of preparation, we found that the catalytic hydrogenation of 3,6-bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one to remove the benzyloxycarbonyl groups resulted in a side reaction. By MS and NMR studies and by preparation of additional 1,2-dihydropyrazin-2-one derivatives, the structure of the byproduct was identified as 3-aminomethyl-5,6-dimethyl-1,2-dihydropyrazin-2-one. Preparation of additional compounds substituted with deuterium provided us with sufficient information to confirm the structure of the product and to support a cyclization mechanism in its formation.

• 公益社団法人日本薬学会の論文
• 2005-09-01

著者

• 津田 喜典

  金沢大学薬学部

• TSUDA Yuko

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• MIYAZAKI Anna

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• OKADA Yoshio

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• Yokoi T

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Tsuda Yuko

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University:cooperative Research Center Of Life Scienc

• Lazarus L

  Medicinal Chemistry Group Lpc National Institute Of Environmental Health Sciences

• Tsuda Y

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Tsuda Yuko

  Faculty Of Pharmaceutical Science Kobe Gakuin University

• Miyazaki A

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Miyazaki Anna

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Okada Yoshio

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• 津田 喜典

  金沢大

• YOKOI Toshio

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• LI Tingyou

  High technology Research Center, Kobe Gakuin University

• LAZARUS Lawrence

  Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environme

• SHIOTANI Kimitaka

  The Graduate School of Food and Medicinal Sciences, Kobe Gakuin University

• YOKOI Toshio

  The Graduate School of Food and Medicinal Sciences, Kobe Gakuin University

• BRYANT Sharon

  Medicinal Chemistry Group, LPC, National Institute of Environmental Health Sciences

• FUJISAWA Yutaka

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• SHIOTANI Kimitaka

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• FUJITA Yoshio

  Faculty of Pharmaceutical Sciences, Kobe Gakuin University

• Okada Y

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Bryant Sharon

  Medicinal Chemistry Group Lpc National Institute Of Environmental Health Sciences

• Li Tingyou

  The Graduate School Of Food And Medicinal Sciences And Faculty Of Pharmaceutical Sciences Kobe Gakui

• Li Tingyou

  High Technology Research Center Kobe Gakuin University

• Yokoi T

  Kobe‐gakuin Univ. Hyogo Jpn

• Fujisawa Yutaka

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Fujita Yoshio

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Okada Yoshihito

  Department Of Pharmacognosy And Phytochemistry Meiji College Of Pharmacy

• Yamamoto T

  R&d Laboratories Nippon Organon K.k.

• Lazarus Lawrence

  Medicinal Chemistry Group Lpc National Institute Of Environmental Health Sciences

• Yokoi Toshio

  Faculty Of Pharmaceutical Sciences And High-technology Research Center Kobe-gakuin University

• Ogino Yoshio

  The Third Department Of Internal Medicine Yeikyo University School Of Medicine

• Tsuda Y

  Faculty Of Pharmaceutical Sciences And High Technology Research Center Kobe Gakuin University

• Shiotani Kimitaka

  The Graduate School Of Food And Medicinal Sciences Kobe Gakuin University

• Shiotani Kimitaka

  Faculty Of Pharmaceutical Sciences Kobe Gakuin University

• Ogino Y

  Teikyo Univ. School Of Medicine Chiba

• Fujita Yoshio

  Faculty Of Engneering Kyoto University.

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