Synthesis of novel 4-hydroxycoumarin derivatives: evaluation of antimicrobial, antioxidant activities and its molecular docking studies

被引:14
作者
Govindhan, M. [1 ,2 ]
Subramanian, K. [1 ]
Rao, K. Chennakesava [3 ]
Easwaramoorthi, K. [4 ]
Senthilkumar, P. [2 ]
Perumal, P. T. [3 ]
机构
[1] Anna Univ, Dept Chem, Chennai 600020, TN, India
[2] Orchid Chem & Pharmaceut Ltd, R&D Ctr, Drug Discovery Res, Chennai 600119, TN, India
[3] Cent Leather Res Inst, CSIR, Div Organ Chem, Chennai 600020, TN, India
[4] Loyola Coll, Dept Chem, Chennai 600034, TN, India
关键词
4-Hydroxycoumarin derivatives; Antimicrobial; Total antioxidant; E. coli DNA gyrase B subunit; Molecular docking; BIOLOGICAL EVALUATION; SIMPLE COUMARINS;
D O I
10.1007/s00044-015-1448-z
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of novel 4-hydroxycoumarin derivatives 4a-n were synthesized by treating 2-(2-oxo-2H-chromen-4-yloxy)acetic acid 3 with various amines. Acid 3 was obtained from the hydrolysis of corresponding ester 2 which was prepared from 4-hydroxycoumarin 1 and ethyl bromoacetate. All synthesized compounds 4a-n were characterized using spectral techniques. The synthesized compounds 4a-n were evaluated for their antimicrobial and total antioxidant activity using in vitro well diffusion method and phosphomolybdenum method, respectively. Amongst all the compounds, 4c has shown potential antimicrobial and antioxidant activity against the standard. All compounds have exhibited good binding energies from -4.46 to -5.70 kcal/mol against 24-kDa DNA gyrase B fragment from E. coli (PDB ID-1KZN) in molecular docking study and amongst them 4c has shown maximum binding energy.
引用
收藏
页码:4181 / 4190
页数:10
相关论文
共 29 条
[1]   Synthesis and biological evaluation of some new coumarin derivatives [J].
Al-Haiza, MA ;
Mostafa, MS ;
El-Kady, MY .
MOLECULES, 2003, 8 (02) :275-286
[2]  
Aliyu AB, 2013, ACTA POL PHARM, V70, P115
[3]   Plasmid encoded antibiotic resistance: acquisition and transfer of antibiotic resistance genes in bacteria [J].
Bennett, P. M. .
BRITISH JOURNAL OF PHARMACOLOGY, 2008, 153 :S347-S357
[4]   Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity [J].
Borges, F ;
Roleira, F ;
Milhazes, N ;
Santana, L ;
Uriarte, E .
CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) :887-916
[5]   Synthesis, X-ray characterization and biological evaluation of some new 2-(4-methy-2-oxo-2H-chromen-7yloxy) acetamide derivatives [J].
Diwakar, Bhagavathula S. ;
Govindh, B. ;
Sastry, Y. Nagendra ;
Kaladhar, D. S. V. G. K. ;
Murthy, Y. L. N. .
MEDICINAL CHEMISTRY RESEARCH, 2015, 24 (04) :1546-1557
[6]   THE PHARMACOLOGY, METABOLISM, ANALYSIS, AND APPLICATIONS OF COUMARIN AND COUMARIN-RELATED COMPOUNDS [J].
EGAN, D ;
OKENNEDY, R ;
MORAN, E ;
COX, D ;
PROSSER, E ;
THORNES, RD .
DRUG METABOLISM REVIEWS, 1990, 22 (05) :503-529
[7]   Flavonoids, coumarins, and cinnamic acids as antioxidants in a micellar system. Structure-activity relationship [J].
Foti, M ;
Piattelli, M ;
Baratta, MT ;
Ruberto, G .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1996, 44 (02) :497-501
[8]  
Georgia M, 2009, EUR J MED CHEM, V44, P3020
[9]   Synthesis, structure, antimicrobial and antioxidant investigations of dicoumarol and related compounds [J].
Hamdi, Naceur ;
Puerta, M. Carmen ;
Valerga, Pedro .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (11) :2541-2548
[10]  
Indu Singh Indu Singh, 2010, International Journal of ChemTech Research, V2, P1745