A new nonsteroidal analgesic-antiinflammatory agent. Synthesis and activity of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone and related compounds.

doi:10.1021/JM00187A013

Paper

A new nonsteroidal analgesic-antiinflammatory agent. Synthesis and activity of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone and related compounds.

Published 1979 · M. Takaya, M. Sato, K. Terashima

Journal of medicinal chemistry

Q1 SJR score

57

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0

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Abstract

In order to examine analgesic and antinflammatory activities, various 2-alkyl- or 2-alkenyl-4-alkoxy-5-(substituted amino)-3(2H)-pyridazinones were prepared. Among the compounds prepared, 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone (8) was evaluated to be the most attractive compound as an analgesic-antiinflammatory agent. Compound 8 was shown to be more potent in analgesic and antiinflammatory activities and less potent in toxicity than aminopyrine and phenylbutazone. Some pyridazinone derivatives in which possible active sites of 8 are eliminated and altered were prepared, and their activities were evaluated by means of analogous assays. On the basis of available data, the structure-activity relationship in a series of 4-alkoxy-2-substituted-5-(substituted amino)-3(2H)-pyridazinones was also discussed.

In Vitro Study

Study Snapshot

4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone (8) is a promising nonsteroidal analgesic-antiinflammatory agent with more potent analgesic and antiinflammatory properties and less toxicity than aminopyrine and phenylbutazone.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

A new nonsteroidal analgesic-antiinflammatory agent. Synthesis and activity of 4-ethoxy-2-methyl-5-morpholino-3(2H)-pyridazinone and related compounds.

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References

Citations

I2-DMSO Promoted Deaminative Coupling Reactions of Glycine Esters: Access to 5-(Methylthio)pyridazin-3(2H)-ones.

I2-DMSO-promoted deaminative coupling of glycine esters with methyl ketones and hydrazine hydrate in DMSO effectively synthesizes 5-(methylthio)pyridazin-3(2H)-one derivatives in good yields.

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This study developed an enantioselective three-component reaction for the synthesis of tetrahydropyridazinones using chiral,-unsaturated acylammonium salts, malonates, and azodicarboxylates

New insights on the arylpiperazinylalkyl pyridazinone ET1 as potent antinociceptive and anti-inflammatory agent.

ET1 is a potent analgesic and anti-inflammatory agent, potentially suitable for clinical applications in various inflammatory-based diseases.

New pyridazine derivatives as selective COX-2 inhibitors and potential anti-inflammatory agents; design, synthesis and biological evaluation.

New pyridazine derivatives show high COX-2 inhibitory activity and potential anti-inflammatory properties, with a superior gastrointestinal safety profile compared to celecoxib and indomethacin.

Synthesis and Biological Evaluation of (E)-N’-Benzylidene-7-methyl-2-propyl-1H-benzo[d] imidazole-5-carbohydrazides as Antioxidant, Anti-inflammatory and Analgesic agents

(E)-N'-Benzylidene-7-methyl-2-propyl-1H-benzo[d]imidazole-5-carbohydrazides show potential as antioxidant, anti-inflammatory, and analgesic agents, with molecular docking studies supporting their binding to COX

A One-Pot Biginelli Synthesis and Characterization of Novel Dihydropyrimidinone Derivatives Containing Piperazine/Morpholine Moiety

This study presents a simple and efficient method for synthesizing novel dihydropyrimidinone derivatives containing piperazine/morpholine moiety in a good yield.

Study on the 4-ethoxy-2-methyl-5-(4-morpholinyl)-3(2H)-pyridazinone using FT-IR, 1H and 13C NMR, UV-vis spectroscopy, and DFT/HSEH1PBE method

The vibrational frequencies and maximum electronic absorption wavelengths of emarfazone are in good agreement with each other, indicating that the molecular structure and electronic absorption parameters are accurate.

Synthesis of 2-substituted-4-aryl-6-phenylpyridazin-3(2H)-ones as potential anti-inflammatory and analgesic agents with cardioprotective and ulcerogenic sparing effects

4-(4-methoxyphenyl)-2-(2-(4-phenylpiperazin-1-yl)-2-oxoethyl)-6-phenylpyridazin-3(2H)-one (17) is an ideal anti-inflammatory agent with COX-2 select

Utilization of Cyanoacetohydrazide and Oxadiazolyl Acetonitrile in the Synthesis of Some New Cytotoxic Heterocyclic Compounds

Cyanoacetohydrazide and oxadiazolyl acetonitrile derivatives show promising cytotoxic activity against various human tumor cell lines and antioxidant properties.