2(3H)-furanones and 2(3H)-pyrrolones: synthesis and antimycobacterial evaluation.
A series of 3-arylidene-5-(substituted phenyl)-2(3H)-furanones (3-10) and their nitrogen analogues, 3-arylidene-5-(substituted phenyl)-1-benzyl-2(3H)-pyrrolone (11-14), and 3-arylidene-5-(substituted phenyl)-2(3H)-pyrrolones (15-21) were synthesized. All the compounds were screened for their antimycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv (ATCC 27294) in BACTEC medium using the Microplate Alamar Blue Assay (MABA). Among the synthesized compounds, compound 19, 3-(4-chlorobenzylidene)-5-(4-methylphenyl)-2(3H)-pyrrolone, emerged as a lead compound having the highest activity against Mycobacterium tuberculosis. The antimycobacterial activity was found to improve upon replacement of oxygen of furanone ring with nitrogen atom (pyrrolones), however, substitution with benzylamine moiety (1-benzylpyrrolones) markedly decreases the activity.
Husain
Asif
A
Faculty of Pharmacy, Jamia Hamdard University, Department of Pharmaceutical Chemistry, Hamdard Nagar, New Delhi-110062, India. drasifhusain@yahoo.com
Alam
Mohammed Mumtaz
MM
Hasan
Syed Misbahul
SM
Yar
Mohammed Shahar
MS
D000995:Antitubercular Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008970:Molecular Weight; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D010078:Oxazines; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology*; D014966:Xanthenes
D000995:Antitubercular Agents; D005663:Furans; D010078:Oxazines; D011758:Pyrroles; D014966:Xanthenes; C005843:resazurin