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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- Miyazaki Anna
- Faculty of Pharmaceutical Sciences, Kobe Gakuin University
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- Fujisawa Yutaka
- Faculty of Pharmaceutical Sciences, Kobe Gakuin University
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- Shiotani Kimitaka
- Faculty of Pharmaceutical Sciences, Kobe Gakuin University
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- Fujita Yoshio
- Faculty of Pharmaceutical Sciences, Kobe Gakuin University
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- Li Tingyou
- High Technology Research Center, Kobe Gakuin University
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- Tsuda Yuko
- Faculty of Pharmaceutical Sciences, Kobe Gakuin University High Technology Research Center, Kobe Gakuin University
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- Yokoi Toshio
- Faculty of Pharmaceutical Sciences, Kobe Gakuin University High Technology Research Center, Kobe Gakuin University
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- Bryant Sharon D.
- Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, U.S.A.
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- Lazarus Lawrence H.
- Medicinal Chemistry Group, Laboratory of Pharmacology and Chemistry, National Institute of Environmental Health Sciences, U.S.A.
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- Okada Yoshio
- Faculty of Pharmaceutical Sciences, Kobe Gakuin University High Technology Research Center, Kobe Gakuin University
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説明
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 by-product 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.
収録刊行物
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- CHEMICAL & PHARMACEUTICAL BULLETIN
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CHEMICAL & PHARMACEUTICAL BULLETIN 53 (9), 1152-1158, 2005
公益社団法人 日本薬学会
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詳細情報 詳細情報について
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- CRID
- 1390282679145677056
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- NII論文ID
- 110003666330
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- NII書誌ID
- AA00602100
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- ISSN
- 13475223
- 00092363
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- NDL書誌ID
- 7409204
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- PubMed
- 16141586
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDLサーチ
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- PubMed
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- 抄録ライセンスフラグ
- 使用不可