2-(phenyl)-4H-chromen-4-ones: Green synthesis, characterization, in vitro antifungal evaluation and molecular docking approach toward Aspergillus fumigatus

Abstract

An effective and greener method for the synthesis of 2-(phenyl)-4H-chromen-4-ones has been developed by reacting 2-hydroxychalcones and tert-butyl hydroperoxide (TBHP) in the presence of a base via ultrasonic irradiation. Ultrasonic irradiation is used to replace conventional energy sources in synthesis. In terms of energy conservation and waste reduction, ultrasonic irradiations are increasingly being used as eco-friendly, green, and clean solutions in organic processes. Antifungal activity of all the synthesized compounds was evaluated against three fungi strains. Compound 4d showed the highest activity against A. fumigatus, R. stolonifer and M. mucedo with the values of 20 ​± ​0.47 ​mm, 19 ​± ​0.46 ​mm and 22 ​± ​0.49 ​mm respectively. Compound 4d also showed highest moldock score and formed H-bond with active amino acids. Compounds bearing lipophilic electron withdrawing groups showed more potent activity compared to compounds having electron donating groups.

Keywords

• Chalcones
• 2-(phenyl)-4H-chromen-4-ones
• Antifungal activity
• Molecular docking
• Chitinase