Novel Antiinflammatory Analgesics: 3-(2-/4-Pyridylethyl)-Benzoxazolinone and Oxazolo[4,5-β]pyridin-2-one Derivatives

Abstract

Twenty‐two new 3‐[2‐(2‐and/or 4‐pyridyl)ethyl]benzoxazolinone and oxazolo[4,5‐b]pyridin‐2‐one derivatives have been synthesized by reacting 2‐and/or 4‐vinylpyridine and appropriate benzoxazolinones and oxazolo[4,5‐b]pyridine‐2‐one. Their chemical structures have been proven by IR, 1H‐NMR, 13C‐NMR, mass spectroscopy, and elemental analysis. The analgesic activities of these compounds were investigated by a modified Koster′s Test. Test results revealed that, at 100 mg/kg dose level, most of the compounds showed significant analgesic activities when compared to aspirin. Therefore the compounds were screened for their antiinflammatory activities using the carrageenan hind paw edema test. Compounds 1, 7, 10, 11, 12, 13, 15, 18, 20, 21 were found more active than indomethacine. In gastric ulceration studies gastrointestinal bleeding was not observed at 100 mg/kg dose level in compounds 1 and 2.

A QSAR Study for Analgesic and Anti‐inflammatory Activities of 5‐/6‐Acyl‐3‐alkyl‐2‐Benzoxazolinone Derivatives

“…2‐Benzoxazolinone scaffold has been popular as having a diverse number of pharmacological activities such as analgesic and anti‐inflammatory . Numerous significant benzoxazolinone derivatives have been found to have analgesic and anti‐inflammatory activity comparable to or higher than that of indomethacin which is used as a medication to reduce pain, fever and swelling from inflammation . In our previous paper, we reported the design, the synthesis, and the pharmacological evaluation of novel 5‐/6‐acyl‐3‐(4‐substituted‐1‐piperazinylmethyl)‐2‐benzoxazolinone derivatives as A and AI agents .…”

Synthesis of Some New Mannich Bases of 6-Acyl-5-Chloro-2-Benzoxazolinones : Bazi Yeni̇ Mannich Bazi 6-Açi̇l-5-Kloro-2-Benzoksazolinonlarin Sentezleri̇

“…Because of this, it is important to find a useful starting substance such as acyl derivatives of benzoxazolinone and it is clear that choosing such a compound is the key step for a medicinal chemist. In our laboratory, some derivatives of 2-benzoxazolinone series have been designed, synthesized and evaluated in the search for new non-steroidal antiinflammatory agents (5)(6)(7)(8)(9). A considerable number of the prepared compounds have shown analgesic-antiinflammatory activity comparable to or higher than that of indomethacine.…”

Synthesis of Novel Oxazolo[4,5‐b]pyridine‐2‐one based 1,2,3‐triazoles as Glycogen Synthase Kinase‐3β Inhibitors with Anti‐inflammatory Potential

“…In continuation to the work performed by our group on benzoxazolinone and 2‐mercaptobenzoxazole‐based 1,2,3‐triazole conjugates as anti‐inflammatory compounds , we extended our studies to oxazolo[4,5‐b]pyridine‐2‐one moiety, the bio‐isostere of benzoxazolinone and 2‐mercaptobenzoxazole. Oxazolopyridinones have been reported to be pharmaceutically important as anti‐nociceptive, anti‐inflammatory, anti‐malarial, and Met kinase inhibitors . Recently, oxazolo‐pyridines have also been reported as potent GSK‐3 β inhibitors .…”