Design and Synthesis of Some Substituted 1H-Pyrazolyl-oxazolidines or 1H-Pyrazolyl-thiazolidines as Anti-inflammatory-Antimicrobial Agents

✍ Scribed by Adnan A. Bekhit; Hesham T. Y. Fahmy

• Publisher: John Wiley and Sons
• Year: 2003
• Tongue: English
• Weight: 181 KB
• Volume: 336
• Category: Article
• ISSN: 0365-6233
• DOI: 10.1002/ardp.200390007

✦ Synopsis

Abstract

Four series of 1 H‐pyrazole derivatives have been synthesized. The first series was synthesized starting with the reaction of 3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐1 H‐pyrazole‐4‐carboxaldehyde 1 with L‐serine, L‐cysteine, or L‐penicillamine, followed by N‐protection using (Boc)~2~O to provide compounds 2. The latter compounds could be N‐deprotected by 4N HCl/dioxane to afford the second series 3 orreactedwith NH~4~OH in the presence of DCC/HOBt to give the corresponding amides 4 followed by N‐deprotection giving rise to compounds 5. The newly synthesized compounds were evaluated for their anti‐inflammatory‐antimicrobial activities. In addition, the ulcerogenic and acute toxicity profiles were determined. Compound 5b (2__RS__, 4__R__)‐2‐[3‐(5‐bromo‐2‐thienyl)‐1‐phenyl‐1__H__‐pyrazol‐4‐yl]‐5‐methylthiazolidine‐4‐carboxamide, proved to be the most active anti‐inflammatory‐antimicrobial agent in the present study with a good safety margine and no ulcerogenic effect.