Efficient and simple synthesis of novel 1, 2, 3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity. Issue 22 (16th November 2020)

• Record Type: Journal Article
• Authors: Adardour, Mohamed; Boutafda, Aziz; Hdoufane, Ismail; Aghraz, Abdellah; Hafidi, Mohamed; Zaballos-García, Elena; Cherqaoui, Driss; Baouid, Abdesselam
• Is Part Of: Synthetic communications. Volume 50:Issue 22(2020)
• Page Start: 3490
• Page End: 3506
• Publication Date: 2020-11-16
• Subjects: Antimicrobial activity -- chemoselective -- molecular docking -- propargyl-benzimidazolone -- regioselective; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2020.1803913
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: In this study, a novel series of 1, 2, 3-triazolyl-benzimidazolone derivatives have been synthesized by click reaction of azides with benzimidazolones 2a–b . The latter compounds were prepared with excellent yields (85–97%), the structures of products were determined by spectral analysis. Then, the X-rays crystallographic analysis of compound 7a revealed the self-assembling properties. The new heterocycles were evaluated for their in vitro antimicrobial activities against Gram-positive and Gram-negative bacteria and against fungi strains. The most tested synthesized compounds showed potent antibacterial and antifungal activities against all tested strains. The compound 6c was found to be the most active, particularly, against Aspergillus niger and Penicillium sp. with the same MIC and MBC of 0.0625 mg/mL. Furthermore, in silico molecular docking studies stipulated a sign of a good correlation between experimental activity and calculated binding affinity. According to the docking results, compound 6d showed minimum binding energy and can be considered as a good antimicrobial agent. Graphical Abstract: