チオセミカルバジド関連化合物の合成(第8報) : 5-メルカプトおよび5-アミノ-s-トリアゾロ[3,4-b][1,3,4]チアジアゾール類について

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In order to obtain compounds with hypoglycemic activity, 5-mercapto- (II) and 5-amino-s-triazolo [3,4-b] [1,3,4]-thiadiazoles (VIII) were synthesized by the application of carbon disulfide and cyanogen bromide to 2-hydrazino-1,3,4-thiadiazoles (I : R=CH_3,C_2H_5,iso-C_3H_7,C_6H_5). By the application of methyl iodide and cyanogen bromide to the 5-mercapto compounds, in the presence of alkali, 5-methylmercapto compound (III : R'=CH_3) and 5-thiocyano compound (III : R'=CN) were prepared. Oxidative chlorination of the 5-mercapto compound using chlorine gave 5-chlorosulfonyl compound which was aminated to 5-sulfamoyl compound (V). Screening of 5-sulfamoyl (V), 5-mercapto (II), and 5-thiocyano-2-isopropyl-s-triazolo [3,4-b] [1,3,4]-thiadiazole (III'R=iso-C_3H_7 was carried out using alloxan-diabetes mice and 5-sulfamoyl and 5-mercapto compounds were found to have stronger activity than BZ-55 used as control.
1967-02-25