SYNTHESIS AND BIOLOGICAL EVALUATION OF INDOLE AND IMIDAZOLE DERIVATIVES

Abstract

2-Chloromethyl-JH-benzimidazole-5-carboxylic acid (1) was prepared. Compound 1 reacted with mercaptoacetic acid to yield S-alkylbenzimidazole derivative 2 which cyclized to form thiazinobenzimidazole derivative 3. New condensation products 4-9 were prepared by the reaction of compounds 2 & 3 with aromatic aldehydes. Esterification of compound 1 yielded compound 10 which reacted with mercaptoacetic acid to yield S-alkylbenzimidazole derivative 11 which reacted with aromatic aldehydes to yield condensation products 13-17. Thiazino-benzimidazole 12 was obtained by heating compound 11 in acetic anhydride. Compound 12 reacted with amines to form the amides 18-21. Reaction of compound 11 with amines followed by cyclization yielded compounds 22-36. Oxidation of compound 3 and reaction with amino acids produced compounds 37-40. New derivatives of 2,3-diphenyl-lH-indole-5-carbonyl chloride (42) were synthesized by the reaction of compound 42 with piperazine forming compound 43. Compound 43 reacted with different acid chlorides, esters and aryl sulfones to yield compounds 44-56. Compound 42 reacted with ethylene diamine forming compound 57 which reacted with different aromatic compounds yielding compounds 58-62. The antiviral activity of the compounds was tested against herpes simplex virus and hepatitis A virus.