New N-phenylacetamide-incorporated 1,2,3-triazoles: [Et3NH][OAc]-mediated efficient synthesis and biological evaluation

被引:40
作者
Akolkar, Satish V. [1 ]
Nagargoje, Amol A. [1 ]
Krishna, Vagolu S. [2 ]
Sriram, Dharmarajan [2 ]
Sangshetti, Jaiprakash N. [3 ]
Damale, Manoj [4 ]
Shingate, Bapurao B. [1 ]
机构
[1] Dr Babasaheb Ambedkar Marathwada Univ, Dept Chem, Aurangabad 431004, Maharashtra, India
[2] Birla Inst Technol & Sci, Dept Pharm, Hyderabad Campus, Hyderabad 500078, India
[3] YB Chavan Coll Pharm, Dept Pharmaceut Chem, Dr Rafiq Zakaria Campus, Aurangabad 431001, Maharashtra, India
[4] Srinath Coll Pharm, Dept Pharmaceut Chem, Aurangabad 431136, MS, India
关键词
ANTITUBERCULAR AGENTS SYNTHESIS; AZIDE-ALKYNE CYCLOADDITION; ONE-POT SYNTHESIS; CLICK CHEMISTRY; IONIC LIQUIDS; TRIAZOLE DERIVATIVES; ANTIFUNGAL ACTIVITY; MOLECULAR DOCKING; FACILE SYNTHESIS; 1,4-DISUBSTITUTED 1,2,3-TRIAZOLES;
D O I
10.1039/c9ra03425k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A facile, highly efficient, and greener method for the synthesis of new 1,4-disubstituted-1,2,3-triazoles was conducted using [Et3NH][OAc] as a medium by the implementation of ultrasound irradiation via click chemistry, affording excellent yields. The present synthetic method exhibited numerous advantages such as mild reaction conditions, excellent product yields, minimal chemical waste, operational simplicity, shorter reaction time, and a wide range of substrate scope. The synthesized compounds were further evaluated for in vitro antifungal activity against five fungal strains, and some of the compounds displayed equivalent or greater potency than the standard drug. A molecular docking study against the modelled three-dimensional structure of cytochrome P450 lanosterol 14 alpha-demethylase was also performed to understand the binding affinity and binding interactions of the enzyme. Furthermore, the synthesized compounds were evaluated for DPPH radical scavenging activity and antitubercular activity against Mycobacterium tuberculosis H37Rv strain.
引用
收藏
页码:22080 / 22091
页数:12
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