1017-06-7

Usage

Uses

Used in Pharmaceutical Research:
4,5-Dihydro-6-(4-methoxyphenyl)pyridazin-3(2H)-one is used as a research compound for exploring its potential pharmacological and biological activities. Its unique structural properties make it a promising candidate for drug development, particularly in the discovery of new therapeutic agents.
Used in Drug Development:
In the pharmaceutical industry, 4,5-Dihydro-6-(4-methoxyphenyl)pyridazin-3(2H)-one is used as a lead compound for the development of novel drugs. Its potential therapeutic effects and structural characteristics allow researchers to investigate its efficacy in treating various diseases and conditions, contributing to the advancement of medical treatments.

InChI:InChI=1/C11H12N2O2/c1-15-9-4-2-8(3-5-9)10-6-7-11(14)13-12-10/h2-5H,6-7H2,1H3,(H,13,14)

Upstream product

• 38102-67-9 4-(3-methoxy-phenyl)-4-oxo-butyric acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 1010800-67-5 tert-butyl 4-(4-methoxyphenyl)-4-oxobutanoate 
• 100-66-3 methoxybenzene 
• 5447-74-5 methyl 3-(4-methoxybenzoyl)propionate 
• 60112-44-9 5-(4-methoxyphenyl)furan-2(3H)-one 
• 3153-44-4 4-(4-methoxy-phenyl)-4-oxo-butyric acid 

Downstream Products

• 142731-44-0 [3-(4-Methoxy-phenyl)-6-oxo-5,6-dihydro-4H-pyridazin-1-yl]-acetic acid methyl ester 
• 76617-83-9 6-(4-Methoxy-phenyl)-6-phenyl-tetrahydro-pyridazin-3-one 
• 2166-33-8 6-(4-methoxyphenyl)-2H-pyridazin-3-one 
• 74190-69-5 3-(4-methoxyphenyl)-1,4,5,6-tetrahydropyridazine 
• 282090-13-5 3-[6-(4-methoxyphenyl)-3(2H)-pyridazinon-2-yl]propanenitrile 
• 129904-89-8 [6-(4-methoxyphenyl)-3(2H)-pyridazinon-2-yl]acetic acid 
• 282090-12-4 3-[6-(4-methoxyphenyl)-3(2H)-pyridazinon-2-yl]propanoic acid 
• 133342-12-8 ethyl [6-(4-methoxyphenyl)-3(2H)-pyridazinon-2-yl]acetate 

Relevant academic research and scientific papers

Synthesis, anti-convulsant activity and molecular docking study of novel thiazole pyridazinone hybrid analogues

Pyridazinone analogues have been known to be potential candidates for anticonvulsant agents. We have identified several pyridazinone-based anticonvulsant agents. As a continuation to our previous research, a series of hybrid pyridazinone-thiazole connected through amide linkage were designed and synthesized. Among these, compound SP-5F demonstrated significant anticonvulsant activity with median effective dose of 24.38 mg/kg (MES) and 88.23 mg/kg (scPTz). Results of GABA estimation showed a marked increase in the GABA level when compared with control. Molecular docking studies at the active site of GABA receptor, further confirmed the GABA modulatory effects of SP-5F.

Design, Synthesis, and Pharmacological Screening of Pyridazinone Hybrids as Anticonvulsant Agents

A series of new hybrid benzimidazole containing pyridazinones derivatives were designed and synthesized in accordance with the pharmacophoric requirements essential for the anticonvulsant activity. The synthesized compounds were evaluated for anticonvulsant activity on mice by the gold standard maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure models. Among the compounds tested, SS-4F showed significant anticonvulsant activity in both the screens with ED50 values of 25.10 and 85.33 mg/kg in the MES and scPTZ screens, respectively. Compound SS-4F emerged as safer and effective anticonvulsant due to its several-fold higher protective indices. Further, the gamma-aminobutyric acid (GABA) estimation result showed a marked increase in the GABA level (1.7-fold) as compared to the control, which was further confirmed by good binding properties with the GABAA receptor.

PRODUCING METHOD OF NITROGEN-CONTAINING ORGANIC COMPOUND

A hydrazine-carbon dioxide-binding compound or hydrazine derivatives 2 carbonyl group react with a compound having one or more nitrogen-containing organic for preparing the compounds of relates to method.

Efficient synthesis, anticonvulsant and muscle relaxant activities of new 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6-phenyl-4,5-dihydropyridazin-3(2H) -one derivatives

A series of 2-(2-(3-(4-chlorophenyl)-6-oxo-5,6-dihydropyridazin-1(4H)yl) acetyl)hydrazine carbothioamide and 2-((5-amino-1,3,4-thiadiazol-2-yl)methyl)-6- (4-chlorophenyl)-4,5-dihydropyridazin-3(2H)-one derivatives were synthesized, characterized, and evaluated for anticonvulsant activity and muscle relaxant activity. The synthesized compounds 5d (82.75 %) and 5e (85.44 %) showed promising anticonvulsant activity by protection against tonic hind limb extensor phase in maximal electroshock model (MES) at (50 mg/kg) compared to standard drug phenytoin and also compounds 5d (82.75 %), and 5e (85.44 %) showed significant anticonvulsant activity by protection against pentylenetetrazole- induced generalized convulsions in pentylenetetrazole model (PTZ) at (100 mg/kg) compared to standard drug diazepam. On the other hand, compound 5e showed significant muscle relaxant activity (84.57 %) by rotarod and traction test model comparing with diazepam as a standard drug.

Design, synthesis and antihypertensive screening of novel pyridazine substituted s-triazin-2-imine/one/thione derivatives

Some new 7-substituted-phenyl-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-imine/one/thione derivatives were synthesized by a sequence of reactions starting from appropriate aryl hydrocarbons. The final compounds were screened for antihypertensive activities by non-invasive method using Tail Cuff method. All the test compounds showed significant antihypertensive activity; 7-(biphenyl-4-yl)-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-imine (4p) exhibited antihypertensive activity more than the reference standard drugs.

Solid-state and solvent-free synthesis of azines, pyrazoles, and pyridazinones using solid hydrazine

Azines, pyrazoles, and pyridazinones were isolated as the sole products in high yields (>97%) by grinding solid hydrazine (H3N +NHCO2-) with di-carbonyl compounds or by their reaction in the absence of solvent. Neither catalysts nor additives were needed to promote the reactions. The solid-state and solvent-free reactions proceeded under ambient conditions and did not produce any wastes other than water and carbon dioxide. They are operationally easy, environmentally safe, and readily scalable, allowing for highly selective synthesis of compounds containing the hydrazine motif. Copyright

Phosphodiesterase inhibitors. Part 5: Hybrid PDE3/4 inhibitors as dual bronchorelaxant/anti-inflammatory agents for inhaled administration

(-)-6-(7-Methoxy-2-(trifluoromethyl)pyrazolo[1,5-a]pyridin-4-yl) -5-methyl-4,5-dihydropyridazin-3(2H)-one (KCA-1490) exhibits moderate dual PDE3/4-inhibitory activity and promises as a combined bronchodilatory/anti- inflammatory agent. N-alkylation of the pyridazinone ring markedly enhances potency against PDE4 but suppresses PDE3 inhibition. Addition of a 6-aryl-4,5-dihydropyridazin-3(2H)-one extension to the N-alkyl group facilitates both enhancement of PDE4-inhibitory activity and restoration of potent PDE3 inhibition. Both dihydropyridazinone rings, in the core and extension, can be replaced by achiral 4,4-dimethylpyrazolone subunits and the core pyrazolopyridine by isosteric bicyclic heteroaromatics. In combination, these modifications afford potent dual PDE3/4 inhibitors that suppress histamine-induced bronchoconstriction in vivo and exhibit promising anti-inflammatory activity via intratracheal administration.

Further studies on 2-arylacetamide pyridazin-3(2H)-ones: Design, synthesis and evaluation of 4,6-disubstituted analogs as formyl peptide receptors (FPRs) agonists

Formyl peptide receptors (FPRs) play an essential role in the regulation of endogenous inflammation and immunity. In the present studies, a large series of pyridazin-3(2H)-one derivatives bearing an arylacetamide chain at position 2 was synthesized and te

Design, synthesis and antihypertensive screening of novel pyridazine substituted s-triazin-2-imine/one/thione derivatives

Some new 7-substituted-phenyl-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3, 5]triazin-2-imine/one/thione derivatives were synthesized by a sequence of reactions starting from appropriate aryl hydrocarbons. The final compounds were screened for antihypertensive activities by non-invasive method using Tail Cuff method. All the test compounds showed significant antihypertensive activity; 7-(biphenyl-4-yl)-3,4,8,9-tetrahydro-2H-pyridazino[1,6-a][1,3,5]triazin-2-imine (4p) exhibited antihypertensive activity more than the reference standard drugs.

Iodine-mediated facile dehydrogenation of dihydropyridazin-3(2H)one

A new protocol for the dehydrogenation of dihydropyridazin-3(2H)-one has been carried out by catalytic amount of iodine in dimethyl sulphoxide in good yield with easy workup.