Synthesis and anti-inflammatory activity of novel (substituted)benzylidene acetone oxime ether derivatives: Molecular modeling study

Herein, we report the design, synthesis, and pharmacological properties of a series of substituted benzylidene acetone oxime ether derivatives from the corresponding oxime derivatives. All the newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carragee...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2010-04, Vol.45 (4), p.1403-1414
Main Authors: El-Gamal, Mohammed I., Bayomi, Said M., El-Ashry, Saadia M., Said, Shehta A., Abdel-Aziz, Alaa A.-M., Abdel-Aziz, Naglaa I.
Format: Article
Language:English
Subjects:
Animals
Anti-inflammatory activity
Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Benzylidene acetone oxime ether derivatives
Biological and medical sciences
Bones, joints and connective tissue. Antiinflammatory agents
Butanones - chemical synthesis
Butanones - chemistry
Butanones - pharmacology
Ethers
Hydrogen Bonding
Magnetic Resonance Spectroscopy
Medical sciences
Models, Molecular
Molecular modeling study
Oximes - chemistry
Pharmacology. Drug treatments
Rats
Spectrophotometry, Infrared
Thermodynamics
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Summary:Herein, we report the design, synthesis, and pharmacological properties of a series of substituted benzylidene acetone oxime ether derivatives from the corresponding oxime derivatives. All the newly synthesized compounds were investigated in vivo for their anti-inflammatory activities using carrageenin-induced rat paw oedema model. Among the compounds examined, compounds 5b and 7a showed the highest activity, nearly equivalent to that of the standard drug diclofenac sodium. Hence, they were screened for their analgesic activities using acetic acid-induced writhing model in mice and also, their ulcerogenic effects were studied. Compound 7a was found to possess significant anti-inflammatory and analgesic activities with negligible ulcerogenic effect. Docking study of the synthesized compound 7a into the active site of COX-1 and COX-2 revealed a similar binding mode to SC-558, a selective COX-2 inhibitor. Compound 7a was found to possess anti-inflammatory activity with negligible ulcerogenic effect and similar binding mode to SC-558, a selective COX-2 inhibitor. [Display omitted]
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2009.12.041