Antimicrobial, antioxidant, cytotoxic and molecular docking properties of N-benzyl-2,2,2-trifluoroacetamide

被引:14
作者
Balachandran, C. [1 ]
Kumar, P. Saravana [1 ]
Arun, Y. [2 ]
Duraipandiyan, V. [3 ]
Sundaram, R. Lakshmi [4 ]
Vijayakumar, A. [5 ]
Balakrishna, K. [1 ]
Ignacimuthu, S. [1 ]
Al-Dhabi, N. A. [3 ]
Perumal, P. T. [2 ]
机构
[1] Loyola Coll, Div Microbiol & Canc Biol, Entomol Res Inst, Madras 600034, Tamil Nadu, India
[2] CSIR Cent Leather Res Inst, Div Organ Chem, Madras 600020, Tamil Nadu, India
[3] King Saud Univ, Coll Sci, Addriyah Chair Environm Studies, Dept Bot & Microbiol, Riyadh 11451, Saudi Arabia
[4] Sri Ramachandra Univ, Cent Res Facil, Madras 600116, Tamil Nadu, India
[5] Loyola Coll, Dept Chem, Madras 600034, Tamil Nadu, India
关键词
Antimicrobial; Antioxidant; Cytotoxic; Molecular docking; N-Benzyl-2,2,2-trifluoroacetamide; FUTURE ANTIFUNGAL THERAPY; AGENTS; TARGETS;
D O I
10.1007/s13204-014-0307-4
中图分类号
TB3 [工程材料学];
学科分类号
0805 ; 080502 ;
摘要
N-Benzyl-2,2,2-trifluoroacetamide was obtained by acylation of benzylamine with trifluoroacetic anhydride using Friedel-Crafts acylation method. The synthesised compound was confirmed by spectroscopic and crystallo-graphic techniques. N-Benzyl-2,2,2-trifluoroacetamide was assessed for its antimicrobial, antioxidant, cytotoxic and molecular docking properties. It showed good antifungal activity against tested fungi and moderate antibacterial activity. The minimum inhibitory concentration values of N-benzyl-2,2,2-trifluoroacetamide against fungi were 15.62 mu g/mL against A. flavus, 31.25 mu g/mL against B. Cinerea and 62.5 mu g/mL against T. mentagrophytes, Scopulariopsis sp., C. albicans and M. pachydermatis. N-Benzyl-2,2,2-trifluoroacetamide showed 78.97 +/- 2.24 of antioxidant activity at 1,000 mu g/mL. Cupric ion reducing antioxidant capacity of N-benzyl-2,2,2-trifluoroacetamide was dependent on the concentration. Ferric reducing antioxidant power assay of N-benzyl-2,2,2-trifluoroacetamide showed (1.352 +/- 0.04 mM Fe(II)/g) twofold higher value compared to the standard. N-Benzyl-2,2,2-trifluoroacetamide showed 75.3 % cytotoxic activity at the dose of 200 mu g/mL with IC50 (54.7 %) value of 100 mu g/mL. N-Benzyl-2,2,2-trifluoroacetamide was subjected to molecular docking studies for the inhibition AmpC beta-lactamase, Glucosamine-6-Phosphate Synthase and lanosterol 14 alpha-demethylase (CYP51) enzymes which are targets for antibacterial and antifungal drugs. Docking studies of N-benzyl-2,2,2-trifluoroacetamide showed low docking energy. N-Benzyl-2,2,2-trifluoroacetamide can be evaluated further for drug development.
引用
收藏
页码:207 / 216
页数:10
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