Reactions of 3-Phenylglycidic Esters. V. Reaction of Methyl 3-(4-Methoxyphenyl) glycidate with 2-Nitroaniline and Synthesis of 1,5-Benzodiazepine Derivatives
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概要
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Stereochemical aspects of the oxirane-ring opening of methyl trans-3-(4-methoxyphenyl)-glycidate (1) with 2-nitroaniline (5) were investigated. ZnI_2 showed good catalytic activity in this reaction, giving the cis-opening product (6a) predominantly. On the other hand, the reaction on the surface of silica gel proceeded predominantly by trans-opening. Silica gel had rather little effect on the reaction of 1 with 2-nitrothiophenol or 2-nitrophenol. Some 1,5-benzodiazepine derivatives (18-21), 1-aza analogues of diltiazem, were synthesized from 6a, b for pharmacological evaluation. Some oxidative epimerization of 9a, b was observed during cyclization in boiling xylene in the presence of air. The cerebral vasodilating activity of 21a, the most potent compound in this series, was about 0.5 that of racemic diltiazem. The structure-activity relationships are discussed.
- 1985-06-25
著者
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井上 博純
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd, .
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武田 幹男
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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長尾 拓
Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.
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長尾 拓
Biological Research Laboratory:tanabe Seiyaku Co. Ltd. :(present Adress)department Of Toxicology And
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村田 栄
Pharmacological Research Laboratory Tanabe Seiyaku Co. Ltd.
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橋山 富樹
Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd.,
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武田 幹男
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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井上 博純
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd .
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橋山 富樹
Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.
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Hashiyama Tomiki
Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.
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