著者

佐々木 正 兼松 顕 大瀬 誠子

出版者

公益社団法人 日本薬学会

雑誌

YAKUGAKU ZASSHI (ISSN:00316903)

巻号頁・発行日

vol.84, no.10, pp.977-983, 1964-10-25 (Released:2010-02-19)

参考文献数

22

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Some diphenyl derivatives were visualized, imitating the A and C rings in the morphine skeleton with the C ring substituted with a phenyl group, as shown in Table I. On the assumption that the angle of A and C rings is necessary for these compounds to show analgesic action by their contact with the cells in the action site, examinations were made for the syntheses of 9-substituted 9, 10-dihydrophenanthrene and 5-substituted 9, 10-dihydro-5H-dibenzo [a, b] cycloheptene.1) 9, 10-Dihydro-9-phenanthrenecarboxylic acid (IV) was obtained in a good yield by the reduction of 9-phenanthrenecarboxylic acid (X) with sodium amalgam. Curtius reaction of the azide of IV afforded ethyl 9, 10-dihydro-9-phenanthrenecarbamate (XIV) but this substance was extremely labile and underwent decomposition on being left at room temperature to form phenanthrene. The acid amide compounds (XVII and XVIII) of IV were stable.2) Reaction of 5-amino-10, 11-dihydro-5H-dibenzo [a, b] cycloheptene (XXII) with methyl iodide in the presence of alkali gave 5-dimethylamino compound (XXIII). Amination of 10-bromo compound (XXV) was attempted in order to obtain 10-dimethylamino compound but the product was found to be 5H-dibenzo [a, b] cyclohepten-5-one (XXVI).