SYNTHESIS, CHARACTERISATION & ANTIFUNGAL ACTIVITY OF QUINOXALINE 2, 3-DIONE DERIVATIVES
Keywords:
Quinoxaline 2,3-Dione, Antimicrobial activity, Anti-fungal activity, Schiff bases reactionsAbstract
A novel series of 15 new quinoxaline 2,3 dione derivatives containing a 4-thiazolidinone(T1-T5), 2-azetidinone(A1-A5),and Imidazolinones (I1-I5) nucleus. Imidazole is a planer five-membered heterocyclic ring system with three carbon and two nitrogen atoms in 1 and 3 positions. Oxo imidazoline, which is also known as imidazolinones is reported to exhibit a wide variety of therapeutic activities such as sedative, hypnotic, CNS depressant etc. The synthesis by reacting N’-substituted arylidene/heteroarylidene Quinoxaline 2,3 dione with thioglycollic acid in the presence of dry benzene, with chloroacetyl chloride in the presence of triethylamine and with 4-benzylidene-2-methyloxazole-5-one in the presence of pyridine respectively. All the title compounds were tested for their antibacterial activity against gram-positive (staphylococcus aureus, staphylococcus epidermidis, Bacillus cereus and pseudomonas aereginosa) and gram-negative (Escherichia coli and klebsiella pneumonia) bacteria, fungal activity against (Aspergillus Niger and Aspergillus fumigates) at a concentration of 100,200?g/ml. The compounds with chloro, hydroxyl and nitro substitution in the three derivatives showed better activity when compared to bromo and fluoro substitution. The synthesize compounds like thiazolidinones, azetidinones and imidazolinones derivatives of quinoxaline 2,3 dione from Schiff base as intermediate. The compounds T1-T5 are Thiazolidinones, compounds A1-A5 are azetidinones and compounds I1-I5 are imidazolinones. Antibacterial activity of synthesized compounds was tested against both gram positive and gram negative bacteria and the standard drug used for the study was ciprofloxacin. The chloro, fluro and bromo substitution in three derivatives showed significant antifungal activity when compared to standard. The hydroxy, nitro groups showed mild activity when compared to standard.
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