Reaction of 3-Phenylglycidic Esters. IV. Reaction of Methyl 3-(4-Methoxyphenyl) glycidate with 2-Nitrophenol and Synthesis of 1,5-Benzoxazepine Derivatives

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概要

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• The reaction of methyl trans-3-(4-methoxyphenyl) glycidate (1) with 2-nitrophenol was investigated under various conditions. Generally, the reaction proceeded predominantly by cis-opening of the oxirane ring of 1 to give the threo-nitro ester (7). Selective trans-opening of 1 was observed only in the reaction with sodium 2-nitrophenoxide to give the erythro-nitro ester (8). Some 1,5-benzoxazepine derivatives (16-19), 1-oxa analogues of diltiazem, were synthesized from 7 and 8 for pharmacological evaluation. Compound 18a showed the highest vasodilating activity in this series, but it was less active and more toxic than racemic diltiazem.

• 1985-02-25

著者

• 井上 博純

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd, .

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 渡辺 章重

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 近田 美紀彦

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 長尾 拓

  Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 渡辺 章重

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 橋山 富樹

  Organic Chemistry Research Laboratory

• 長尾 拓

  Department Of Toxicology And Pharmacology Faculty Of Pharmaceutical Sciences University Of Tokyo

• 村田 栄

  Biological Research Laboratory

• 村田 栄

  Pharmacological Research Laboratory Tanabe Seiyaku Co. Ltd.

• 橋山 富樹

  Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 井上 博純

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd .

• 近田 美紀彦

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 橋山 富樹

  Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.

• Hashiyama Tomiki

  Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.

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