Synthesis, antimicrobial and antifungal activity of a new class of spiro pyrrolidines.
A new class of spiro pyrrolidines, dispiro[oxindole-cyclohexanone]pyrrolidines, dispiro[oxindole-tetrahydronaphthalen-1-one]pyrrolidines, dispiro[oxindole-arylidene-cyclohexanone]pyrrolidines, dispiro[oxindole-hexahydro-indazole]pyrrolidines, and spiro[butenolide]pyrrolidines, 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.
Raj
A Amal
AA
Department of Organic Chemistry, Center for Advanced Studies in Botany, University of Madras, Guindy Campus, Chennai, India 600 025.
Raghunathan
R
R
SrideviKumari
M R
MR
Raman
N
N
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D003883:Arthrodermataceae / Q000187:drug effects; D003500:Cyclization; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D011759:Pyrrolidines; D013141:Spiro Compounds