2166-33-8

Usage

Uses

Used in Pharmaceutical Industry:
p-Anisylpyridazone is used as a key intermediate in the synthesis of Gabazine, a GABA-A receptor antagonist, for its application in treating neurological disorders and as an adjunct in anesthesia.
Additionally, p-Anisylpyridazone is utilized in the production of several analgesic pharmaceuticals, contributing to the development of pain-relief medications and enhancing their efficacy in managing various types of pain.

Upstream product

• 298-12-4 Glyoxilic acid 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 862816-15-7 4-(4-methoxy)phenyl-2-hydroxy-4-oxobutyric acid ethyl ester 
• 1316302-31-4 ethyl 2-benzoyl-4-(4-methoxyphenyl)-4-oxobut-2-enoate 
• 1017-06-7 6-(4-Methoxyphenyl)-4,5-dihydro-2H-pyridazin-3-one 
• 1010800-67-5 tert-butyl 4-(4-methoxyphenyl)-4-oxobutanoate 
• 3153-44-4 4-(4-methoxy-phenyl)-4-oxo-butyric acid 

Downstream Products

• 133342-12-8 ethyl [6-(4-methoxyphenyl)-3(2H)-pyridazinon-2-yl]acetate 
• 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 

Relevant academic research and scientific papers

Novel pyridazinone derivatives as butyrylcholinesterase inhibitors

In the current study, forty-four new [3-(2/3/4-methoxyphenyl)-6-oxopyridazin-1(6H)-yl]methyl carbamate derivatives were synthesized and evaluated for their ability to inhibit electric eel acetylcholinesterase (EeAChE) and equine butyrylcholinesterase (eqB

Copper-mediated rapid and facile oxidative dehydrogenation of dihydrobenzocarbazoles

Rapid method for the oxidative dehydrogenation of dihydrobenzocarbazoles has been introduced by using bench scale and commercially available reagent; copper chloride, in excellent yield with easy workup. The scope of the reaction has been studied with broad range of substitutes.

Rhodium(III)-Catalyzed Alkynylation of 4-Arylphthalazin-1(2H)-one Scaffolds via C-H Bond Activation

Selective C–H bond alkynylation toward modular access to material and pharmaceutical molecules is of great desire in modern organic synthesis. Disclosed herein is rhodium(III)-catalyzed selective C–H bond mono-/bialkynylation of 4-aryl phthalazin-1(2H)-one was developed. The silver salt AgSbF6 are demonstrated to play a vital role in promoting the bialkynylation reactions. The present alkynylation strategy is simple, efficient, and features high functional group tolerance and broad substrate scope under an air atmosphere. Additionally, 6-aryl pyridazin-3(2H)-one scaffold is amenable to the selective monoalkynylation and sequential bialkynylation, respectively.

Synthesis and Bioevaluation of 3,6-Diaryl-[1,2,4]triazolo[4,3-b] Pyridazines as Antitubulin Agents

A series of 3,6-diaryl-[1,2,4]triazolo[4,3-b]pyridazines were designed as a class of vinylogous CA-4 analogues. The easily isomerized (Z,E)-butadiene linker of vinylogous CA-4 was replaced by a rigid [1,2,4]triazolo[4,3-b]pyridazine scaffold. Twenty-one target compounds were synthesized and exhibited moderate to potent antiproliferative activity. The compound 4q with a 3-amino-4-methoxyphenyl moiety as the B-ring, comparable to CA-4 (IC50 = 0.009-0.012 μM), displayed the highly active antiproliferative activity against SGC-7901, A549, and HT-1080 cell lines with IC50 values of 0.014, 0.008, and 0.012 μM, respectively. Tubulin polymerization experiments indicated that 4q effectively inhibited tubulin polymerization, and immunostaining assay revealed that 4q significantly disrupted tubulin microtubule dynamics. Moreover, cell cycle studies revealed that compound 4q dramatically arrested cell cycle progression at G2/M phase in A549 cells. Molecular modeling studies showed that 4q could bind to the colchicine binding site on microtubules.

Synthesis of some new 2,6-disubstituted-3(2H)-pyridazinone derivatives and investigation of their analgesic, anti-inflammatory and antimicrobial activities

In this study, 12 new 3(2H)-pyridazinone derivatives carrying 4-substituted phenylpiperazinylethyl moiety on lactam nitrogen were synthesized and their chemical structures were confirmed by 1H-NMR, mass, and elemental analysis. Analgesic and anti-inflammatory activities of the synthesized compounds were evaluated in mice. Among the synthesized compounds, compound 9c showed the best analgesic and anti-inflammatory activities without causing any gastric effect in stomachs of tested animals. In addition, the synthesized compounds were screened for their antibacterial and antifungal activities against some pathogenic strains.

Synthesis of some new 3(2H)-pyridazinone derivatives and evaluation of their analgesic-anti-inflammatory and antimicrobial activities

In this study, 15 new 3(2H)-pyridazinone derivatives carrying N'-(4-substitutedphenylmethylidene)acetohydrazide moiety on lactam nitrogen were synthesized and their chemical structures were confirmed by 1H-NMR, mass, and elemental analysis. Analgesic and anti-inflammatory activities of the synthesized compounds were evaluated in mice. Among the synthesized compounds, compound 11e exhibited the best analgesic and anti-inflammatory activities, without causing any gastric effect in stomachs of tested animals. Additionally, the synthesized compounds were screened for their antibacterial and antifungal activities against some pathogenic strains.

Copper-catalyzed aerobic dehydrogenation of C-C to C=C bonds in the synthesis of pyridazinones

A simple and efficient procedure for the synthesis of pyridazin-3(2H)-ones through copper-catalyzed dehydrogenation of a single C-C bond of 4,5-dihydropyridazin-3(2H)-ones to a C=C bond with oxygen as the terminal oxidant is described. Functional groups including hydroxy, carboxylic, bromo, chloro, cyano, nitro and alkoxy were all tolerated under the reaction conditions. Moreover, this methodology was applied to the preparation of a series of structurally similar N-substituted 6-phenylpyridazinone compounds containing fluorine. The dehydrogenation reactions exhibit good yields and selectivity. Copper-catalyzed dehydrogenation of a C-C bond of 4,5-dihydropyridazinones to a C=C bond with oxygen as the terminal oxidant is described. Various functional groups were tolerated under the reaction conditions. The method was also applied to the preparation of a series of N-substituted 6-phenylpyridazinones containing fluoride. The dehydrogenation reactions exhibit good yields and selectivity.

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.

Unexpected C-C bond cleavage: A route to 3,6-diarylpyridazines and 6-arylpyridazin-3-ones from 1,3-dicarbonyl compounds and methyl ketones

An unexpected C-C bond cleavage has been revealed in the absence of metal. This observation has been exploited to develop an efficient approach toward 3,6-diarylpyridazines and 6-arylpyridazin-3-ones from simple and commercially available 1,3-dicarbonyl compounds and methyl ketones.

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.