Synthesis and pharmacological evaluation of N-substituted 4,6-diaryl-3-pyridazinones as Analgesic, antiinflammatory and antipyretic agents.

Rubat, Catherine; Coudert, Pascal; Tronche, P; Bastide, J.; Bastide, P; Privat, Alain

doi:10.1248/cpb.37.2832

Cited by 29 publications

(9 citation statements)

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“…A large number of pyridazinone derivatives were reported to exhibit insecticidal [1][2][3][4][5], herbicidal [2,6], antiallergenic [7], antihypertensive [8], analgesic [9], anti-inflammatory [10], and bacteriocidal activities [11]. This prompted us to synthesize a new series of heterocyclic pyridazinone derivatives through the reaction of 4-(p-bromophenyl) or 4-(p-methylphenyl)-4-oxo-2-butenoic acid 1a,b [12] with benzylamine in dry benzene and yielded the addition products 2a,b.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new pyridazin‐3‐one derivatives and their utility in heterocyclic synthesis

El-Mobayed

Hussein

Mohlhel³

2010

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Synthesis of new heterocyclic compounds containing the pyridazinone moiety, which have a valuable biological activities, has been achieved through the nucleophilic addition of benzylamine to 4-(p-substituted phenyl)-4-oxo-2-butenoic acid 1a,b, followed by cyclocondensation of the adducts 2a,b to the corresponding pyridazin-3-one derivatives 3a,b. The behavior of the latter compounds toward different nucleophilic and electrophilic reagents was investigated. The structures of the newly synthesized compounds were elucidated by elemental analysis and spectroscopic data.

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Section: Introductionmentioning

confidence: 99%

Synthesis of some new pyridazin‐3‐one derivatives and their utility in heterocyclic synthesis

El-Mobayed

Hussein

Mohlhel³

2010

Journal of Heterocyclic Chem

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“…The presence of an 4-(fluorophenyl)-piperazine group in position 6 increases the analgesic activity. It was reported that fluorophenylpiperazine and trifloromethylphenylpiperazine moiety on the amine part of these compounds have positive influences on their antinociceptive activity [11,12,16,18]. A moderate activity was generally shown by all remaining compounds.…”

Section: Pharmacology (Tables 2 and 3)mentioning

confidence: 97%

“…Our experience in the pyridazinone field [5][6][7][8], together with the observation that some pyridazine derivatives such as emorfazone [9], on the market in Japan, and pyridazinones bearing an alkylpiperazinyl alkyl moiety [10][11][12][13][14][15][16][17][18], show interesting antinociceptive activity. Their activity mechanism is not related to effects on prostaglandins or opioid system.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Analgesic and Anti-inflammatory Activity of Ethyl (6-Substituted-3(2H)-pyridazinone-2-yl)acetate Derivatives

Dündar

Gökçe

Küpeli

et al. 2011

Arzneimittelforschung

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A number of 6-substituted-3(2H)-pyridazinones and the corresponding methyl (6-substituted-3(2H)-pyridazinone-2-yl)acetate derivatives carrying the arylpiperazinyl structure present in potent antinociceptive agents reported in the literature were synthesized. As part of a programme a series of diverse arylpiperazine derivatives of ethyl (6-substituted-3(2H)-pyridazinone-2-yl)acetate were prepared and tested for their in vivo analgesic and anti-inflammatory activity by using p-benzoquinone-induced writhing test and carrageenan-induced hind paw edema model, respectively. Side effects of the compounds were examined on gastric mucosa. None of the compounds showed gastric ulcerogenic effect compared with reference non-steroidal anti-inflammatory drugs (NSAIDs). On the basis of available data, the structure-activity relationship in the series of ethyl (6-substituted-3(2H)-pyridazinone-2-yl)acetate derivatives was also discussed. When compared to parent 6-substituted-3(2H)-pyridazinones, the new ester derivatives, for example ethyl (6-4-[(2-fluoro)phenyl]piperazine-3(2H)-pyridazinone-2-yl)acetate exhibited better analgesic and anti-inflammatory activity and a lower ulcerogenic effect.

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“…) . Furthermore, various 3(2 H )‐pyridazinone derivatives have been reported as analgesic and anti‐inflammatory agents with low ulcerogenic effect . Structure activity relationship (SAR) studies employing pyridazinone system revealed that N ‐substitution was required for good in vitro COX‐2 inhibitory activity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some Novel 2,6‐Disubstituted Pyridazin‐3(2H)‐one Derivatives as Analgesic, Anti‐Inflammatory, and Non‐Ulcerogenic Agents

Ibrahim

Loksha

Elshihawy

et al. 2017

Archiv der Pharmazie

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Some novel 2,6-disubstituted pyridazine-3(2H)-one derivatives were synthesized and evaluated for in vitro cyclooxygenase-2 (COX-2) inhibitory efficacy. Compounds 2-{[3-(2-methylphenoxy)-6-oxopyridazin-1(6H)-yl]methyl}-1H-isoindole-1,3(2H)-dione (5a), 2-propyl-6-(o-tolyloxy)pyridazin-3(2H)-one (6a), and 2-benzyl-6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridazin-3(2H)-one (16a) showed the most potent COX-2 inhibitory activity with IC values of 0.19, 0.11, and 0.24 μM, respectively. The synthesized compounds with the highest COX-2 selectivity indices were evaluated for their anti-inflammatory, analgesic, and ulcerogenic activities. Compounds 6a and 16a demonstrated the most potent and consistent anti-inflammatory activity over the synthesized compounds, which was significantly higher than that of celecoxib in the carrageenin rat paw edema model and with milder ulcer scoring than that of indomethacin in the ulcerogenicity screening.

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Synthesis and pharmacological evaluation of N-substituted 4,6-diaryl-3-pyridazinones as Analgesic, antiinflammatory and antipyretic agents.

Cited by 29 publications

References 1 publication

Synthesis of some new pyridazin‐3‐one derivatives and their utility in heterocyclic synthesis

Synthesis of some new pyridazin‐3‐one derivatives and their utility in heterocyclic synthesis

Synthesis and Analgesic and Anti-inflammatory Activity of Ethyl (6-Substituted-3(2H)-pyridazinone-2-yl)acetate Derivatives

Synthesis of Some Novel 2,6‐Disubstituted Pyridazin‐3(2H)‐one Derivatives as Analgesic, Anti‐Inflammatory, and Non‐Ulcerogenic Agents

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