Document Detail

Syntheses of new tetrasubstituted thiophenes as novel anti-inflammatory agents.
MedLine Citation:
PMID:  17336429     Owner:  NLM     Status:  MEDLINE    
A series of new tetrasubstituted thiophenes (4a-4i, 5a-5i and 6a-6f) have been synthesized as novel anti-inflammatory agents and were evaluated for their anti-inflammatory activity in carrageenin-induced rat hind paw oedema model at the doses of 10, 20 and 40mg/kg body weight. Among ester series, the best compound 4c showed 71% protection at 10mg/kg, 72% at 20mg/kg, and 76% at 40mg/kg to inflamed paw; while in acid series 5a showed 79% protection at 10mg/kg, 80% at 20mg/kg, and 70% at 40mg/kg, and 5c showed 72% protection at 10mg/kg, 75% at 20mg/kg, and 69% at 40mg/kg, to inflamed paw. In case of oxime series 6a-6f, the anti-inflammatory activities of the candidates were found to be poor as compared to acid and ester series. It was found on the basis of SAR studies of target compounds, that the presence of OCH(3) at R(2) position and H, OCH(3) at R(1) are one of the requirements for eliciting comparable anti-inflammatory activity in both tetrasubstituted thiophenes' ester and acid series. Compounds 4a-4i, 5a-5i were investigated for their analgesic activity in acetic acid induced writhing response model at 10mg/kg dose. Among the ester series compound 4e showed maximum protection of 60%, while 4a, 4b, and 4i exhibited 55%, 45%, and 43% protection, respectively. The result showed that presence of H, Cl at R(1) and OCH(3), CH(3) at R(2) in tetrasubstituted thiophene ester series enhances their analgesic activity. The candidates of acid series 5a-5i showed poor analgesic activity as compared to the standard drug ibuprofen. Compounds 4a-4i, 5a-5i were evaluated for their in vitro antioxidant nitric oxide radical scavenging assay. Among the ester series 4a showed maximum in vitro nitric oxide radical scavenging activity having IC(50) value 30.08microg/ml while in acid series 5a has IC(50) value 25.20microg/ml. The results showed that the presence of R(1)=H, R(2)=OCH(3) and R(1)=R(2)=OCH(3) enhances nitric oxide radical scavenging property in tetrasubstituted thiophenes' acid series.
Khurshid I Molvi; Kamala K Vasu; Swapnil G Yerande; Vasudevan Sudarsanam; Navedul Haque
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Publication Detail:
Type:  Journal Article     Date:  2007-01-24
Journal Detail:
Title:  European journal of medicinal chemistry     Volume:  42     ISSN:  0223-5234     ISO Abbreviation:  Eur J Med Chem     Publication Date:  2007 Aug 
Date Detail:
Created Date:  2007-07-27     Completed Date:  2007-11-06     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0420510     Medline TA:  Eur J Med Chem     Country:  France    
Other Details:
Languages:  eng     Pagination:  1049-58     Citation Subset:  IM    
School of Pharmacy, Faculty of Medical Sciences, Jimma University, P.O. Box 378, Jimma, Oromia, Ethiopia.
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MeSH Terms
Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
Disease Models, Animal
Dose-Response Relationship, Drug
Edema / chemically induced,  drug therapy
Structure-Activity Relationship
Thiophenes / chemical synthesis*
Reg. No./Substance:
0/Anti-Inflammatory Agents, Non-Steroidal; 0/Thiophenes

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