Cellulose‐Supported CuI‐Nanoparticles‐Mediated Green Synthesis of Trifluoromethylbenzoate‐Linked Triazoles for Pharmacological & DFT study

• Published in: ChemistrySelect (Weinheim) 2019-01, Vol.4 (2), p.759-764
• Main Authors: Deswal, Sonal, Tittal, Ram Kumar, Yadav, Pinki, Lal, Kashmiri, Vikas D., Ghule, Kumar, Nikhil
• Format: Article
• Language: English
• Subjects: Antifungal; Antimicrobial; Cell-CuI-NPs; DFT study; Trifluoromethylbenzoate
• ISSN: 2365-6549; 2365-6549
• DOI: 10.1002/slct.201803099

A green heterogeneous catalyst cellulose‐supported CuI‐nanoparticles employed for efficient synthesis of 4‐trifluoromethylbenzoate‐linked triazole in high yield from 4‐trifluoromethyl‐benzoic acid prop‐2‐ynyl ester and aryl/benzyl azide under aqueous condition. All triazoles were successfully characterized by IR, 1H‐NMR, 13C‐NMR, HRMS and finally supported by X‐ray crystallographic structure of 4‐trifluoromethyl‐benzoic acid 1‐phenyl‐1H‐[1,2,3]triazol‐4‐ylmethyl ester. Antibacterial study revealed that triazoles substituted by 4‐NO2 and 4‐Cl group to the benzyl and benzene ring displayed good to comparable activity as compare to commonly used drug ciprofloxacin. Likewise, triazoles substituted with a 4‐NO2 group on benzyl ring, unsubstituted aryl and 4‐F substituted aryl showed better antifungal activity when compared with commonly used antifungal drug fluconazole. Further, the computational study by DFT (B3PW91) level with 6–311G(d,p) basis set studied chemical reactivities, chemical hardness and molecular stability of triazole by frontier molecular orbital and molecular electrostatic potential study. The DFT results were in good agreement with pharmacological studies. Noble antifungal and antimicrobial active new 4‐trifluoromethylbenzoate linked triazoles were synthesized in environment friendly green reaction condition using Cell‐CuI‐NPs as heterogeneous catalyst in water in high yield. All triazoles were characterized by IR, 1H‐NMR, 13C‐NMR, HRMS and finally supported by single crystal structure of 5 a. Antifungal and antibacterial activities of these synthesized new triazole molecules are very much comparable to commonly used antifungal and antibacterial drug Fluconazole and Ciprofloxacin, respectively. The pharmacological study results are in good agreement with DFT results by frontier molecular orbital and molecular electrostatic potential study.