Synthesis and biological evaluation of 2 (3-arylisoxazol-5-yl)methyl 6-fluoro-4-oxo-4H-chro3 mene-2-carboxylates as antioxidant and antimicrobial agents

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Kumaraswamy Battula
Sirassu Narsimha
Vasudeva Reddy Nagavelli
Mutheneni Srinivasa Rao

Abstract

A series of novel (3-arylisoxazol-5-yl)methyl 6-fluoro-4-oxo-4H-
-chromene-2-carboxylate derivatives (C1C12) were synthesized by the Cu(I)-
-catalyzed reaction of in situ generated nitrile oxides with prop-2-ynyl 6-flu­oro-4-oxo-4H-chromene-2-carboxylate in good yields and their antioxidant and antimicrobial activities were investigated. Among all the synthesized com­pounds, C1 (IC50: 16.43±0.57 µM) and C12 (IC50:15.98±0.72 µM) registered good antioxidant activity as compared to the standard drug trolox. Compounds C1, C3 and C6 registered very good inhibition against all the tested Gram-posi­tive and Gram-negative bacterial strains with MIC values ranging from 9.375 to 37.5 µg mL-1. Compounds C7C11 registered good inhibition against Bacil­lus subtilis and Staphylococcus aureus with MIC values ranging from 18.75 to 37.5 µg mL-1. Compounds C10 and C11 against Pseudomonas aeroginosa showed more prominent activity than the standard drug penicillin (MIC: 12.5 µg mL-1) with an MIC value of 9.375 µg mL-1 (≈1.33-fold more potent than penicillin). Compounds C7C9 registered good to moderate antifungal activity against the four tested fungal strains with MIC values ranging from 18.75 to 37.5 µg mL-1.

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How to Cite
[1]
K. Battula, S. Narsimha, V. R. Nagavelli, and M. Srinivasa Rao, “Synthesis and biological evaluation of 2 (3-arylisoxazol-5-yl)methyl 6-fluoro-4-oxo-4H-chro3 mene-2-carboxylates as antioxidant and antimicrobial agents”, J. Serb. Chem. Soc., vol. 82, no. 1, pp. 1–12, Feb. 2017.
Section
Organic Chemistry
Author Biographies

Kumaraswamy Battula, Department of Chemistry, Kakatiya University, Warangal-506009

Chemistry

Sirassu Narsimha, 1Department of Chemistry, Kakatiya University, Warangal-506009

Chemistry

Vasudeva Reddy Nagavelli, Kakatiya University, Warangal, Telangana-506009

Chemistry

Mutheneni Srinivasa Rao, Chemical Biology Laboratory, Indian Institute of Chemical Technology, Hyderabad- 500007

Biology

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