Chiral β-arylalkyl-1H-1,2,4-triazoles as demethylase inhibitors: Biological evaluation and its stereoselective interaction with sterol 14α-demethylase from Penicillium digitatum

• Published in: Pesticide biochemistry and physiology Vol. 99; no. 2; pp. 189 - 193
• Main Authors: Cao, Xiufang, Chen, Changshui, Lu, Wenchang, Ke, Shaoyoung
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier 01.02.2011
• Subjects: antifungal properties; azoles; Biological and medical sciences; cultured cells; Fundamental and applied biological sciences. Psychology; Fungal plant pathogens; pathogens; Penicillium digitatum; Phytopathology. Animal pests. Plant and forest protection; Evaluation; Plant pathogen; Nitrogen heterocycle; Interaction; Pesticides; Binding constant; Penicillium digitatum; P. digitatum; Organic nitrogen compounds; Molecular docking; Fungi; Stereoselectivity; Chirality; Chiral triazole; Triazole derivatives; Mould; Inhibitor; Fungi Imperfecti; Inhibition; Molecular domain; Organic compounds; Inhibitory activity
• ISSN: 0048-3575; 1095-9939
• DOI: 10.1016/j.pestbp.2010.12.003

A series of chiral β-arylalkyl-1H-1,2,4-triazole derivatives were prepared and both their in vitro antifungal activities against Penicillium digitatum and binding activity toward CYP51 protein of P. digitatum (PdCYP51) were tested. In general, the in vitro inhibitory activities of R- and S-enantiomers were in good agreement with the corresponding binding activities in cultured cells. Furthermore, the preliminary molecular docking modeling of representative compounds are described to provide more insight into their stereoselective interaction, as well as further rationalize the observations of the activities of chiral azoles as demethylase inhibitors for defense against postharvest pathogens.