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Computer Aided Discovery of Potential Anti-Inflammatory (S)-Naproxen Analogs as COX-2 Inhibitors.
MedLine Citation:
PMID:  22946530     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
A series of substituted 2-(6-methoxynapthalen-2-yl) propanoic acid (naproxen) analogs were synthesized. (S)-naproxen (1) was treated with thionyl chloride to yield acid chloride (2) which was then reacted with different heterocyclic moieties and aryl acids to yield the (S)-naproxen analogs (3a-k). All the compounds were screened for anti-inflammatory activity using in vivo rat paw oedema model and most of the active ones were investigated for their ulcerogenic potential. In silico studies (molecular modeling and docking) were carried out to recognize the hypothetical binding motif of the title compounds with the cyclooxygenase isoenzymes (COX-1 and COX-2) employing Maestro (Version 9.1, Schrodinger, LLC.) software. 2-(1-(2(2-methoxynaphthalen-6-yl)propanoyl)-1H-indol-2-yl) acetic acid (3k) was found to be the most active compound amongst the series with inhibition of paw edema volume by 62.1%, in silico sitemap score of -0.40kcal/mol and ulcerogenic index as least as 1.19.
Authors:
N M Raghavendra; K Ramakrishna; V Sirisha; P Divya; A Venkateswara Rao
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-8-29
Journal Detail:
Title:  Medicinal chemistry (Shariqah (United Arab Emirates))     Volume:  -     ISSN:  1875-6638     ISO Abbreviation:  Med Chem     Publication Date:  2012 Aug 
Date Detail:
Created Date:  2012-9-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101240303     Medline TA:  Med Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Pharmaceutical Chemistry, Gokaraju Rangaraju College of Pharmacy, Osmania University, Hyderabad 500 090, Andhra Pradesh, India. nmraghava@yahoo.in.
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