2-aryl-5-benzoxazolealkanoic acid derivatives with notable antiinflammatory activity.

Abstract

The synthesis and antiinflammatory activity of 5-substituted 2-arylbenzoxazoles are described. Initial screening on carrageenin-induced rat paw edema showed that alpha-methylacetic substitution in the 5 position was preferable to substitutions with the equivalent esters, amides, alcohols, amines or tetrazoles. Halogen substitution in the aryl ring led to the most active compounds which were 2-(4-chlorophenyl)-alpha-methyl-5-benzoxazoleacetic acid (14) and 2-(4-fluorophenyl)-alpha-methyl-5-benzoxazoleacetic acid (29). These compounds were three to five times more active than phenylbutazone as assessed from ED30 values determined on rat paw edema 5 hr after single oral doses.

• Authors: D W Dunwell, D Evans, T A Hicks
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 18 Issue 1 Pg. 53-8 (Jan 1975) ISSN: 0022-2623 [Print] United States
• PMID: 1109576 (Publication Type: Journal Article)

Chemical References

• Anti-Inflammatory Agents
• Carboxylic Acids
• Oxazoles
• Carrageenan

Topics

• Animals
• Anti-Inflammatory Agents (chemical synthesis, therapeutic use, toxicity)
• Carboxylic Acids (chemical synthesis, therapeutic use, toxicity)
• Carrageenan
• Edema (chemically induced, drug therapy)
• Female
• Lethal Dose 50
• Oxazoles (chemical synthesis, therapeutic use, toxicity)
• Plethysmography
• Rats