Anti-nociceptive and anti-inflammatory activity of some (2-benzoxazolone-3-yl and 2-benzothiazolone-3-yl) acetic acid derivatives

Dogruer, Deniz S.; Ünlü, Serdar; Şahi̇n, Mustafa; Yqilada, Erdem

doi:10.1016/s0014-827x(97)00017-7

Cited by 70 publications

(37 citation statements)

References 6 publications

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“…Our research group has been interested for some time in studying the effect of substituting selected aromatic rings in current NSAIDs with alternative heteroaromatic moieties such as 2-oxo-3H-benzoxazole, 2-oxo-3H-benzothiazole and 3(2H)-pyridazinone [11][12][13][14][15]. We are particularly interested in whether the biological activity of the derivatives can be preserved by isosteric replacement of a key aromatic ring.With this purpose and based on the fact that heteroaryl acetic acid derivatives bear potential analgesic and anti-inflammatory activities, we have previously studied the 2-oxo-3H-benzoxazole alkanoic acid derivatives and found that 6-or 7-acyl-2-oxo-3H-benzoxazole alkanoic acids had potent analgesic and anti-inflammatory activities [16,17].…”

Section: Introductionmentioning

confidence: 99%

Investigations of New Pyridazinone Derivatives for the Synthesis of Potent Analgesic and Anti‐Inflammatory Compounds with Cyclooxygenase Inhibitory Activity

Ökçelik

Ünlü

Banoğlu

et al. 2003

Archiv der Pharmazie

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In this study we describe the synthesis of two novel 4-phenyl-and 4-(2-chlorophenyl)-6-(5-chloro-2-oxo-3H-benzoxazol-7-yl)-3(2H)-pyridazinone derivatives (compounds 8a and b) and their testing as inhibitors of cyclooxygenases (COX-1 and COX-2). Both compounds inhibited COX-1 (by 59 % and 61 % for compounds 8a and 8b respectively and COX-2 (by 37 % and 28 % for compounds 8a and 8b respectively) at a concentration of 10 microM. Furthermore, we tested the analgesic and anti-inflammatory activities of the synthesized compounds in vivo by using the p-benzoquinone-induced writhing test and the carrageenan-induced hind paw edema model, respectively. Compounds 8a and 8b showed potent analgesic and anti-inflammatory activities without causing gastric lesions in the tested animals.

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Section: Introductionmentioning

confidence: 99%

Investigations of New Pyridazinone Derivatives for the Synthesis of Potent Analgesic and Anti‐Inflammatory Compounds with Cyclooxygenase Inhibitory Activity

Ökçelik

Ünlü

Banoğlu

et al. 2003

Archiv der Pharmazie

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“…It is well known that heteroaryl acetic acid derivatives have analgesic properties.With this purpose, some studies have focused on 2-benzoxazolinone alkanoic acid derivatives to develop potent and safer NSAIDs without gastric side effects [7][8][9]. It has been demonstrated that 6-acyl function attached to the benzene portion of benzoxazolinone ring is favorable for analgesic activity in these derivatives and it has been shown that (6-acyl-2-benzoxazolinone-3-yl)alkanoic acid derivatives possessed potent analgesic and anti-inflammatory activities with reduced gastric toxicity [7].…”

Section: Introductionmentioning

confidence: 99%

Amide Derivatives of [5-Chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic Acids as Potential Analgesic and Anti-Inflammatory Compounds

Banoğlu

Ökçelik

Küpeli

et al. 2003

Arch. Pharm. Pharm. Med. Chem.

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In this study, we have explored the prevention of gastric side effects such as gastric lesions and bleeding while maintaining the high analgesic and anti-inflammatory activities by the derivatization of the carboxylate moiety into amides in [5-chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic acids. We have tested the analgesic and anti-inflammatory activities of the synthesized compounds in vivo by using p-benzoquinone-induced writhing test and carrageenan-induced hind paw edema model, respectively. Compounds 3a, 3d, 3e, 3j and 3k potent analgesic and anti-inflammatory activities without gastric lesions in the tested animals. Therefore, conversion of the carboxylate moiety into certain amide derivatives generated potent analgesic and anti-inflammatory compounds while eliminating the gastrointestinal side effects. Cyclooxygenase (COX)-selectivity of the active compounds was also investigated by using in vitro human whole blood assay. Compounds 3a, 3e, 3h and 3k selective inhibition of COX-2 to some extent although the inhibitory activity was not very potent.

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“…We previously reported that N-[2-(4-methylpyridinyl)]-2-[2(3H)-benzazolone-3-yl]acetamide and 4-[2-(6-benzoyl-2-benzoxazolone-3-yl)acetyl]morpholine had significant antinociceptive activity in comparison with the others compounds synthesized [7,8] . In addition, we found that 3-[3-(4-phenylpiperazine-1-yl)propyl)]-2(3H)-benzothiazolone was more active as antinociceptive than the other synthesized compounds [9] .…”

Section: Introductionmentioning

confidence: 99%

Studies on Some 3(2H)-Pyridazinone Derivatives with Antinociceptive Activity

Dogruer¹,

Şahi̇n²,

Ünlü³

et al. 2000

Arch. Pharm. Pharm. Med. Chem.

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Anti-nociceptive and anti-inflammatory activity of some (2-benzoxazolone-3-yl and 2-benzothiazolone-3-yl) acetic acid derivatives

Cited by 70 publications

References 6 publications

Investigations of New Pyridazinone Derivatives for the Synthesis of Potent Analgesic and Anti‐Inflammatory Compounds with Cyclooxygenase Inhibitory Activity

Investigations of New Pyridazinone Derivatives for the Synthesis of Potent Analgesic and Anti‐Inflammatory Compounds with Cyclooxygenase Inhibitory Activity

Amide Derivatives of [5-Chloro-6-(2-chloro/fluorobenzoyl)-2-benzoxazolinone-3-yl]acetic Acids as Potential Analgesic and Anti-Inflammatory Compounds

Studies on Some 3(2H)-Pyridazinone Derivatives with Antinociceptive Activity

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