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Synthesis, antimicrobial, anticancer evaluation and QSAR studies of 6-methyl-4-[1-(2-substituted-phenylamino-acetyl)-1H-indol-3-yl]-2-oxo/thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl esters.
MedLine Citation:
PMID:  22154835     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A series of 6-methyl-4-[1-(2-substituted-phenylamino-acetyl)-1H-indol-3-yl]-2-oxo/thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl esters (1-16) were synthesized and evaluated in vitro for their antimicrobial and anticancer potential. 6-Methyl-4-{1-[2-(4-nitro-phenylamino)-acetyl]-1H-indol-3-yl}-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (15, pMIC(ec) = 2.50 μM/mL) was found to be almost equipotent to the standard drug, norfloxacin (pMIC(ec) = 2.61 μM/mL) against Escherichiacoli and emerged as most potent antimicrobial agent (pMIC(am) = 1.84 μM/mL). 4-{1-[2-(2-Chloro-4-nitro-phenylamino)-acetyl]-1H-indol-3-yl}-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (4, IC(50) = 5 μg/mL) was more potent than the standard drug 5-fluorouracil (IC(50) = 6 μg/mL) against HCT-116 a colon cancer cell line, and emerged as the most potent anticancer agent. The QSAR studies demonstrated the importance of topological parameter, Balaban index (J) followed by lipophillic parameter, log P in describing the antimicrobial activity of the synthesized compounds.
Authors:
Sandeep Kumar Sharma; Pradeep Kumar; Balasubramanian Narasimhan; Kalavathy Ramasamy; Vasudevan Mani; Rakesh Kumar Mishra; Abu Bakar Abdul Majeed
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-11-22
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  -     ISSN:  1768-3254     ISO Abbreviation:  -     Publication Date:  2011 Nov 
Date Detail:
Created Date:  2011-12-13     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Copyright Information:
Copyright © 2011 Elsevier Masson SAS. All rights reserved.
Affiliation:
Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak 124001, India.
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