Synthesis of 2,3‐Dihydro Flavone Coumarins as a Class of Potent Antifungal and Anti‐inflammatory Agents

An efficient, mild and environmentally benign method has been developed for the synthesis of 2,3‐dihydroflavonecoumarins. The reaction of 2‐hydroxyacetophenones 2 with 4‐formylcoumarin 3 using anhydrous potassium carbonate as a mild base. All the synthesized compounds were evaluated for their antifu...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2018-03, Vol.3 (12), p.3451-3458
Main Authors: Shaikh, Farzanabi, Shastri, Samundeeswari, Chougala, Bahubali M., Holiyachi, Megharaja, Shastri, Lokesh A., Joshi, Shrinivas D., Sunagar, Vinay A.
Format: Article
Language:English
Subjects:
2,3-dihydroflavonecoumarins
Anti-inflammatory
Antifungal
Molecular docking
Mycobacterium tuberculosis
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Summary:An efficient, mild and environmentally benign method has been developed for the synthesis of 2,3‐dihydroflavonecoumarins. The reaction of 2‐hydroxyacetophenones 2 with 4‐formylcoumarin 3 using anhydrous potassium carbonate as a mild base. All the synthesized compounds were evaluated for their antifungal activity against Candida albicans, Aspergillus flavus and Aspergillus niger fungal strains by broth dilution method. The tested compounds have exhibited promising in vitro potency with low MIC values rangs from 0.4 to 3.12 μg/mL. The in vitro anti‐inflammatory potency of synthesized compounds by gelatin zymography is comparable to tetracycline and is found to be excellent against Matrix metalloproteinase (MMP‐2). Molecular docking study was performed for all the synthesized compounds with binding site of Cytochrome P450 14 alpha‐sterol demethylase (CYP51) from Mycobacterium tuberculosis in complex with fluconazole PDB (1EA1) and results obtained are quite promising. An efficient, mild and environmentally benign method has been developed for the synthesis of 2,3‐dihydroflavonecoumarins. The reaction of 2‐hydroxyacetophenone with 4‐formylcoumarin using anhydrous potassium carbonate as a mild base. All the synthesized compounds were evaluated for their antifungal activity against C. albicans, A. flavus and A. niger fungal strains. The in vitro anti‐inflammatory potency of synthesized compounds against MMP‐2 has shown excellent results. Molecular docking study was performed for all the synthesized compounds and results obtained were quite promising.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201800120