Synthesis, Antimicrobial and Antifungal Activity of a New Class of Spiro pyrrolidines

• Published in: Bioorganic & medicinal chemistry 2003-02, Vol.11 (3), p.407-419
• Main Authors: Raj, A.Amal, Raghunathan, R, SrideviKumari, M.R, Raman, N
• Format: Article
• Language: English
• Subjects: Anti-Bacterial Agents; Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - pharmacology; Arthrodermataceae - drug effects; Biological and medical sciences; Cyclization; Gram-Negative Bacteria - drug effects; Humans; Medical sciences; Microbial Sensitivity Tests; Pharmacology. Drug treatments; Pyrrolidines - chemical synthesis; Pyrrolidines - pharmacology; Spiro Compounds - chemical synthesis; Spiro Compounds - pharmacology; Staphylococcus aureus - drug effects; Stereoisomerism; Structure-Activity Relationship
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/S0968-0896(02)00439-X

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-hexahydro-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. Graphic