Facile synthesis of non-steroidal anti-inflammatory active bisbenzamide-containing compounds

A variety of N, N′-bis{2-[1,2-ethanediylbis(oxy-2,1-phenylene)]-1-(substituted carbonyl)ethenyl}benzamides 7a– c, 9a– d were synthesized via nucleophilic attack of either primary 8 or secondary amines 6 on bisoxazol-5(4 H)-one 5. The latter was obtained through the reaction of 2,2′-[1,2-ethanediylbi...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2006-12, Vol.14 (24), p.8527-8532
Main Authors: Girgis, Adel S., Ellithey, Mohey
Format: Article
Language:English
Subjects:
Animals
Anti-inflammatory
Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis
Anti-Inflammatory Agents, Non-Steroidal - chemistry
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Benzamides - chemical synthesis
Benzamides - chemistry
Benzamides - pharmacology
Biological and medical sciences
Bisbenzaldehydes
Bisbenzamides
Bisoxazol-5(4 H)-ones
Bones, joints and connective tissue. Antiinflammatory agents
Carrageenan - toxicity
Edema - chemically induced
Edema - pathology
Edema - prevention & control
Female
Foot
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Rats
Rats, Wistar
Structure-Activity Relationship
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Summary:A variety of N, N′-bis{2-[1,2-ethanediylbis(oxy-2,1-phenylene)]-1-(substituted carbonyl)ethenyl}benzamides 7a– c, 9a– d were synthesized via nucleophilic attack of either primary 8 or secondary amines 6 on bisoxazol-5(4 H)-one 5. The latter was obtained through the reaction of 2,2′-[1,2-ethanediylbis(oxy)]bisbenzaldehyde ( 4) with hippuric acid in acetic anhydride in the presence of anhydrous sodium acetate. The anti-inflammatory properties of the prepared compounds were screened using carrageenan-induced paw oedema in rats. Many of the prepared bisbenzamide-containing compounds show considerable in vivo anti-inflammatory activity, especially 7b which reveals remarkable pharmacological properties comparable with ketoprofen (which was used as a reference standard) at successive time intervals (1, 2, 3, 4 and 24 h).
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2006.08.032