402617-95-2Relevant academic research and scientific papers
Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles
Patel, Pallav D.,Patel, Maulik R.,Kocsis, Bela,Kocsis, Erika,Graham, Steven M.,Warren, Andrew R.,Nicholson, Stacia M.,Billack, Blase,Fronczek, Frank R.,Talele, Tanaji T.
experimental part, p. 2214 - 2222 (2010/09/08)
In an effort to find inhibitors that are effective against both Candida and Aspergillus spp., a series of 5(6)-(un)substituted benzotriazole analogs, represented by compounds 3a-3h and 3b′-3f′, were prepared using a crystalline oxirane intermediate 1 previously synthesized in our laboratory. All the compounds were evaluated for inhibitory activity against various species of Candida and Aspergillus. Compounds 3b′ (5,6-dimethylbenzotriazol-2-yl derivative), 3d (5-chlorobenzotriazol-1-yl derivative) and 3e′ (6-methylbenzotriazol-1-yl derivative) exhibited potent antifungal activity, with the MICs for Candida spp. and Aspergillus niger, ranging from 1.6 μg/mL to 25 μg/mL and 12.5 μg/mL to 25 μg/mL, respectively. The present work describes the design, synthesis, regioisomer characterization (through COSY and NOESY 2D-NMR spectroscopy and single molecule X-ray crystallography), antifungal evaluation, molecular docking, and structure-activity relationships of the various 5(6)-(un)substituted benzotriazole analogs.
