Studies on chemotherapeutics. VIII. On the antimicrobial activity and syntheses of diphenylamino derivatives (author's transl)

Abstract

1) Sodium 2-chloro-5-nitrobenzenesulfonate was reacted with the corresponding anilines in water, sealed in a tube, and 4-substituted 4-nitrodiphenylamine sulfonates (I-VI) were obtained. These salts were hydrolyzed with hydrochloric acid to the corresponding 4'-substituted 4-nitrodiphenylamines (VII-XI), and they were reduced with stannous chloride and hydrochloric acid to the 4'-substituted 4-aminodiphenylamines (XII-XVI). 2) Sodium alkoxides of 4-hydroxy-4-nitrodiphenylamine were reacted with the corresponding alkyl halogenides in ethanol and the 4'-alkoxy-4-nitrodiphenylamines (XVII and XVIII) so formed were reduced with zinc and ammonium chloride to the 4'-alkoxy-4-aminodiphenylamines (XIX and XX). The N-ethl-4-methyl-4'-amino-diphenylamine (XXII) was obtained by the reduction of N-ethyl-4-methyl-4'-nitro-diphenylamine (XXI) with zinc and ammonium chloride. 3) The compounds XXIII to LII were obtained by the reaction of haloacetyl chloride with the corresponding amino compounds in acetic acid. The iodo compounds (LIII to LXII) were obtained by the reaction of the corresponding chloroacetylamino compounds with potassium iodide in acetone. 4) Antibacterial activity of these compounds were examined and XXXVI, XXXVII, XLII, XLVI, and LX showed a strong antibacterial activity.