Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity

被引：16

作者：

Adardour, Mohamed ^{[1
]}

Boutafda, Aziz ^{[2
]}

Hdoufane, Ismail ^{[1
]}

Aghraz, Abdellah ^{[3
]}

Hafidi, Mohamed ^{[2
,4
]}

Zaballos-Garcia, Elena ^{[5
]}

Cherqaoui, Driss ^{[1
]}

Baouid, Abdesselam ^{[1
]}

机构：

[1] Univ Cadi Ayyad, Fac Sci Semlalia, Dept Chem, Lab Mol Chem, Marrakech 40001, Morocco

[2] Univ Cadi Ayyad, Fac Sci Semlalia, Dept Biol, Lab Ecol & Environm,MARK Herbarium, Marrakech, Morocco

[3] Univ Cadi Ayyad, Fac Sci Semlalia, URAC35 Assoc Unit, Lab Biotechnol Protect & Valorizat Plant Resource, Marrakech, Morocco

[4] Mohamed VI Polytech Univ UM6P, Benguerir, Morocco

[5] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia, Spain

来源：

SYNTHETIC COMMUNICATIONS | 2020年 / 50卷 / 22期

关键词：

Antimicrobial activity; chemoselective; molecular docking; propargyl-benzimidazolone; regioselective; 1,3-DIPOLAR CYCLOADDITION; BIOLOGICAL EVALUATION; DERIVATIVES; ANTIOXIDANT; DESIGN; ANTIBACTERIAL; AZIDES;

D O I：

10.1080/00397911.2020.1803913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, a novel series of 1,2,3-triazolyl-benzimidazolone derivatives have been synthesized by click reaction of azides with benzimidazolones2a-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 compound7arevealed the self-assembling properties. The new heterocycles were evaluated for theirin vitroantimicrobial 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 compound6cwas found to be the most active, particularly, againstAspergillus nigerandPenicilliumsp. with the same MIC and MBC of 0.0625 mg/mL. Furthermore,in silicomolecular docking studies stipulated a sign of a good correlation between experimental activity and calculated binding affinity. According to the docking results, compound6dshowed minimum binding energy and can be considered as a good antimicrobial agent.

引用

页码：3490 / 3506

页数：17

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[21] Surfactant Protein-C Chromatin-Bound Green Fluorescence Protein Reporter Mice Reveal Heterogeneity of Surfactant Protein C-Expressing Lung Cells [J].