Synthesis and antimicrobial activity of a number of pyrroloindole derivatives

A method for the predominant synthesis of linear pyrroloindoles was developed, based on the attachment of the pyrrole ring to indoline and including diazo coupling of 5-and 6-aminoindolines followed by reduction, condensation with pyruvic acid ethyl ester, and indolization of the resulting 5-and 6-indolinylhydrazines. The in vitro antimicrobial, tuberculostatic, and antifungal activities of a number of 3H,6H-pyrrolo[3,2-e]indole, 1H,7H-pyrrolo[3,2-f]indole, and 1H,5H-pyrrolo[3,2-f]indole derivatives were studied. 1-(p-Chlorophenylazo)-3H,6H-pyrrolo[3,2-e]indole (XIX) and 3,5-di(p-chlorophenylazo)-1H,7H-pyrrolo[3,2-f]indole (XXIII) had high, 1-(p-nitrophenylazo)-3H,6H-pyrrolo[3,2-e]indole (XX) had moderate, and 2,7-diethoxycarbonyl3H,6H-pyrrolo[3,2-e]indole (XVIII) had weak tuberculostatic activity. 3,5-p-Chlorophenylazo)-1H,7H-pyrrolo[3,2-f]indole (XXIII) had high activity against Gram-negative bacteria.