Synthesis and biological activity of the metabolites of (3,4-bis(4-methoxyphenyl)-5-isoxazolyl)acetic acid.

Yamawaki, Ichiro; Ogawa, Kazuo

doi:10.1248/cpb.36.3142

Cited by 11 publications

(8 citation statements)

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“…Writhing test. [15] Groups of mice (n = 8) were treated p.o. with a solution of 6, 7, 9 g, or 9 s-9 w at a dose of 10 or 30 mg kg À1 , or with solvent (1 % ethanol and 0.5 % CMC in distilled water) at a volume of 10 mL kg À1 of animal.…”

Section: -Amino-2-ethoxy-n-(2-trifluoromethylphenyl)benzamide (9 W)mentioning

confidence: 99%

“…[19] Although 5 exhibits only a weak analgesic effect, [20] 3 and 4 are potent analgesics. [14][15][16][17][18] In view of the molecular similarity of these COX-1 inhibitors, it was suggested that it might be possible to obtain analgesic activity using a different scaffold. To further examine this idea, we developed a new COX-1 inhibitor, TFAP (7), [21] whose mo-lecular structure is clearly distinct from those of the above COX-1 inhibitors.…”

Section: Introductionmentioning

confidence: 99%

“…Known COX‐1 inhibitors include mofezolac ( 3 ),14, 15 FR122047 ( 4 )16–18 and SC‐560 ( 5 ) 19. Although 5 exhibits only a weak analgesic effect,20 3 and 4 are potent analgesics 14–18.…”

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of Novel Cyclooxygenase‐1 Inhibitors as Analgesics: 5‐Amino‐2‐ethoxy‐N‐(substituted‐phenyl)benzamides

et al. 2011

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We previously found that N-(4-aminophenyl)-4-trifluoromethylbenzamide (TFAP), a COX-1 inhibitor, exhibits an analgesic effect without causing gastric damage. Unfortunately, TFAP causes reddish purple coloration of urine, and its analgesic effect is less potent than that of indomethacin. Herein we describe our study focusing on the development of 4- and 5-amino-2-alkoxy-N-phenylbenzamide scaffolds, designed on the basis of the structures of TFAP and parsalmide, another known COX-1 inhibitory analgesic agent. 5-Amino-2-ethoxy-N-(2- or 3-substituted phenyl)benzamide derivatives exhibited analgesic activity in a murine acetic acid induced writhing test. Among these compounds, 5-amino-2-ethoxy-N-(2-methoxyphenyl)benzamide (9 v) possesses potent COX-1 inhibitory and analgesic activities, similar to those of indomethacin. In addition, 5-amino-2-ethoxy-N-(3-trifluoromethylphenyl)benzamide (9 g) showed a more potent analgesic effect than indomethacin or 9 v without causing apparent gastric damage or coloration of urine, although its COX-1 inhibitory activity was weaker than that of indomethacin or 9 v. Thus, 9 g and 9 v appear to be promising candidates for analgesic agents and are attractive lead compounds for further development of COX-1 inhibitors.

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Section: -Amino-2-ethoxy-n-(2-trifluoromethylphenyl)benzamide (9 W)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design and Synthesis of Novel Cyclooxygenase‐1 Inhibitors as Analgesics: 5‐Amino‐2‐ethoxy‐N‐(substituted‐phenyl)benzamides

et al. 2011

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“…There are only a few currently available COX‐1 inhibitors, including SC‐560 ( 1 ),13 mofezolac ( 2 ),14–16 and FR122047 ( 3 )17, 18 (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Effect of the oral absorption of benzenesulfonanilide-type cyclooxygenase-1 inhibitors on analgesic action and gastric ulcer formation

Zheng

Oda

Harada

et al. 2008

Journal of Pharmaceutical Sciences

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“…The isoxazoles belong to an important structural group found in a variety of anticonvulsants [8], antivirals [9], and analgesics [10]. Many papers have been published describing the synthesis of isoxazole derivatives [11].…”

mentioning

confidence: 99%

Synthesis of 1,2,5,6‐/1,2,3,6‐tetrahydropyridinyl‐tetrahydro‐cyclopentaisoxazole derivatives

Ahn¹,

Park²,

Lee³

et al. 2003

Journal of Heterocyclic Chem

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Synthesis and biological activity of the metabolites of (3,4-bis(4-methoxyphenyl)-5-isoxazolyl)acetic acid.

Cited by 11 publications

References 0 publications

Design and Synthesis of Novel Cyclooxygenase‐1 Inhibitors as Analgesics: 5‐Amino‐2‐ethoxy‐N‐(substituted‐phenyl)benzamides

Design and Synthesis of Novel Cyclooxygenase‐1 Inhibitors as Analgesics: 5‐Amino‐2‐ethoxy‐N‐(substituted‐phenyl)benzamides

Effect of the oral absorption of benzenesulfonanilide-type cyclooxygenase-1 inhibitors on analgesic action and gastric ulcer formation

Synthesis of 1,2,5,6‐/1,2,3,6‐tetrahydropyridinyl‐tetrahydro‐cyclopentaisoxazole derivatives

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