The Medicinal Chemistry of Some Steroidal Indoxylidene Carboxylic Acids and Derivatives

Abstract

3 r3-hydroxy- 5-androsten-17 -one (1) condensed .in alkaline conditions with 2-nitnobenzaldelwde to give a steroidal indoxylidene carboxylic acid~, which 1 on refluxing in acetic anhydride gave a 3,3 - diacetyl deri vat i ve (.QL. Reduction of (5) with sodium bcrohydride in ethanol gave the indole(ll which was cyclised to the lactam@l by refluxing in acetic anhydride. 3r3 - hydroxyandrostan-17- one 0V gave the steroidal' indoxylidene carboxylic acidOO)on treatment with 2-nitrobenzaldehyde in alkaline conditions. Compound (10) cyclised to the Lact.am (11) on heating with acetic anhydride and was also reduced to the indole (12) by sodium borohydride in ethanol. Compound (12) was cyclised to the lactam~3) on refluxing in acetic anhydride.