SYNTHESIS OF 7-SUBSTITUTED-2,3-DIPHENYL­ INDOLE DERIVATIVES OF EXPECTED BIOLOGICAL ACTIVITY

Abstract

Indoles are known to possess a great variety of pharmacological properties, therefore our first goal in this thesis was to synthesize new indole derivatives and to introduce new rings and side chains of expected pharmacological activity to the indole moiety. Besides, our second aim was to test the cytotoxic activity of the new compounds.

Synthesis of ?-Substituted 2,3-Diphenylindole Derivatives of Expected Biological Activity [Schemes 1-4]

2,3-Diphenyl-1H-indole-7-carbonyl chloride (2) was prepared by treating 2,3-diphenyl-1H-indole-7-carboxylic acid (1) with thionyl chloride.

The reaction of 2 with ammonia yielded 2,3-diphenyl-1H-indole-7- carboxamide (3) which was cyclized to 5,6-diphenyl-1H-pyrrolo[3,2,1- ij]-quinazoline-1,3-2H-dione (4), to 6,7-diphenyl-2,3-dihydro-[1,4]di­ azepino[6,7,1-hi]indole-1,4-dione (5) using ethyl chloroformate, ethyl chloroacetate or chloroacetyl chloride. 4-Imino-1,2-diphenyl-4,5- dihydropyrrolo[3,2,1-ij]quinolin-6-one (6) was obtained from (2) and acetonitrile , respectively. Ethanolysis of compound 6 yielded 3-(2,3-diphenyl-lH-indol-7- yl)-3-oxo-propionimidic acid ethyl ester (7) which was condensed with ethylenediamine and phenylenediamine to afford 7-(2,3-diphenyl-1H­ indol-7-yl)-2,3,4,6-tetrahydro[l,4]diazepin-5-ylideneamine (8) and 4- (2,3-diphenyl-1H-indol-7-yl)-1,3-dihydrobenzo[b][I,4]diazepin-2- ylideneimine (9).