Design and synthesis of two indol-steroid derivatives

In this study two new indol-steroid derivatives were synthesized. The first stage involves the synthesis of 17-(2-amino-thiazol-5-yl)- 10,13-dimethyl-1,2-6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-one (3) by the reaction of progesterone with thiourea using I2 as catalyst. The second stage was achieved by reaction of a brucine derivative with the compound 3 to form the compound N-(2,3-dimethoxystrychnidin-10-ylenamino)-N'-[10,13-dimethyl-17(2-amino-thiazol-5-yl)-1,2,6,7,8,9,10,11,12,13,14,15,16,17- tetradecahydro-cyclopenta-[a]phenanthren-3-ylidene]-ethane-1,2-diamine using boric acid as catalyst. The third stage was achieved by reaction of compound 3 with brucine to form 10,13-dimethyl-17-[2-(2,3-dimethoxy-strychnidin-10-ylideneamino)-thiazol-5-yl]- 1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-onausing boric acid as catalyst. The structure of compounds obtained was confirmed by spectrometry data.