Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines

A new class of spiro pyrrolidines, dispiro[oxindole-cyclohexanone]pyrrolidines,(1) dispiro[oxindole-tetrahydronaphthalen-1-one]pyrrolidines,(2) dispiro[oxindole-arylidene-cyclohexanone]pyrrolidines,(3) dispiro[oxindole-hexabydro-indazole]pyrrolidines,(3) and spiro[butenolide]pyrrolidines,(4) have been screened for their antibacterial and antifungal activity against ten human pathogenic bacteria and four dermatophytic fungi. They were found to have antimicrobial and antifungal activity compounds against various pathogens except Bacillus subtilis. The spiro pyrrolidinines were synthesized by the regioselective 1,3-dipolar cycloaddition reaction of azomethine ylides generated either from isatin and sarcosine or from aziridine. The azomethine ylide so generated reacted with various dipolarophiles such as 2-arylidene-cyclohexanones, 2-arylidene-tetrahydronapthalen-1-ones, 2,6-bis(arylmethylidene)cyclohexanones and 3-arylidene-5-phenyl- butenolides. (C) 2002 Elsevier Science Ltd. All rights reserved.