Synthesis, antifungal activity and docking study of 2-amino-4H-benzochromene-3-carbonitrile derivatives.

Pathogenic fungi are associated with diseases ranging from simple dermatosis to life-threatening infections, particularly in immunocompromised patients. During the past two decades, resistance to established antifungal drugs has increased dramatically and has made it crucial to identify novel antimicrobial compounds. Here, we selected 12 new compounds of 2-amino-4 H -benzochromene-3-carbonitrile drivetives ( C1-C12 ) for synthesis by using nano-TiCl 4 .SiO 2 as efficient and green catalyst, then nine of synthetic compounds were evaluated against different species of fungi, positive gram and negative gram of bacteria. Standard and clinical strains of antibiotics sensitive and resistant fungi and bacteria were cultured in appropriate media. Biological activity of the 2-amino-4 H -benzochromene-3-carbonitrile derivatives against fungi and bacteries were estimated by the broth micro-dilution method as recommended by clinical and laboratory standard institute (CLSI). In addition minimal fangicidal and bactericial concenteration of the compounds were also determined. Considering our results showed that compound 2-amino-4-(4-methyl benzoate)-4 H -benzo[ f ]chromen-3-carbonitrile ( C9 ) had the most antifungal activity against Aspergillus clavatus, Candida glabarata, Candida dubliniensis, Candida albicans and Candida tropicalis at concentrations ranging from 8 to ≤128 μg/mL. Also compounds 2-amino-4-(3,4-dimethoxyphenyl)-4 H -benzo[ f ]chromen-3-carbonitrile ( C4 ) and 2-amino-4-(4-isopropylphenyl)-4 H -benzo[ f ]chromen-3-carbonitrile ( C3 ) had significant inhibitory activities against Epidermophyton floccosum following 2-amino-4-(4-methylbenzoate)-4 H -benzo[ f ]chromen-3-carbonitrile ( C9 ), respectively. Docking simulation was performed to insert compounds C3 , C4 and C9 in to CYP51 active site to determine the probable binding model. [ABSTRACT FROM AUTHOR]