Cyclic Guanidines. V. Synthesis of Hypoglycemic 2,2- and 3,3-Diphenylimidazo [1,2-a] [1,3]-diazacycloalkane Derivatives
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概要
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Synthesis of 2,2- and 3,3-diphenylimidazo [1,2-a] [1,3] diazacycloalkane derivatives (4) and (5) was attempted. The cyclization of 2-(ω-chloroalkylimino)-4,4-diphenylimidazolidines (3) was not advantageous because it gave a mixture of 4 and 5 in low yield. 5,5-Diphenylhydantoin (6) was alkylated at the N_3 or O_2 position and successive reduction of the remained carbonyl group of the products resulted in success. The 3-N-alkylated compounds (14) prepared from 6 selectively gave 4. The 2-O-ethyl derivative (19) afforded 2-(ω-chloroalkylimino) derivatives (21). Heating 21 gave 2-oxo-bicyclic guanidines (22), and treatment of 21 with sodium hydride yielded 3-oxo-bicyclic guanidines (17) in good yield, respectively. Sodium bis (2-methoxyethoxy) aluminum hydride reduction of 17 and 22,having a carbonyl group in the molecule, gave 4 and 5,respectively. Under the same conditions, N-methyl-2-oxo- or 3-oxo-bicyclic guanidines (18) and (28) gave partially reduced products. The bicyclic guanidines (4) and (5) showed potent hypoglycemic activity.
- 社団法人日本薬学会の論文
- 1979-04-25
著者
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今野 常生
Research Institute Daiichi Seiyaku Co. Ltd.
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東 邦雄
Drug Delivery System Institute Ltd.
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東 邦雄
Research Institute, Daiichi Seiyaku Co., Ltd.,
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小笹山 瑛
Research Institute, Daiichi Seiyaku Co., Ltd.
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石川 文義
Research Institute, Daiichi Seiyaku Co., Ltd.
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石川 文義
Research Institute Daiichi Seiyaku Co. Ltd.
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小笹山 瑛
第一製薬
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小笹山 瑛
Research Institute Daiichi Seiyaku Co. Ltd.
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