2166-34-9

Usage

InChI:InChI=1/C16H12N2O/c19-15-11-14(12-7-3-1-4-8-12)16(18-17-15)13-9-5-2-6-10-13/h1-11H,(H,17,19)

Upstream product

• 82231-91-2 3-oxo-5,6-diphenyl-2,3-dihydro-pyridazine-4-carboxylic acid 
• 351416-08-5 2-methoxymethyl-5,6-diphenyl-2H-pyridazin-3-one 
• 27062-58-4 3-chloro-5,6-diphenylpyridazine 
• 491876-40-5 5-bromo-2-hydroxymethyl-6-phenyl-3(2H)-pyridazinone 
• 98-80-6 phenylboronic acid 
• 791839-96-8 6,7-diphenyl-[1,2,4]triazolo[4,3-b]pyridazine-3(2H)-thione 
• 90766-97-5 5-bromo-6-phenylpyridazin-3(2H)-one 
• 5344-88-7 benzil monohydrazone 
• 54108-26-8 ethyl 2,3-dihydro-5,6-diphenyl-3-oxopyridazine-4-carboxylate 
• 71-43-2 benzene 
• 1028-70-2 5,6-diphenyl-4,5-dihydropyridazin-3(2H)-one 
• 6307-19-3 3,4-diphenyl-4-oxobutanoic acid 
• 53647-50-0 ethyl 3-benzoyl-3-phenylpropionate 
• 451-40-1 phenyl benzyl ketone 

Downstream Products

• 134049-63-1 8-(6-Oxo-3,4-diphenyl-6H-pyridazin-1-yl)-octanoic acid methyl ester 
• 134049-61-9 9-(6-Oxo-3,4-diphenyl-6H-pyridazin-1-yl)-nonanoic acid methyl ester 
• 27062-58-4 3-chloro-5,6-diphenylpyridazine 

Relevant academic research and scientific papers

Pyridazines. Part 35: Traceless solid phase synthesis of 4,5- and 5,6-diaryl-3(2H)-pyridazinones

A new method for the traceless solid phase synthesis of 3(2H)-pyridazinones has been developed employing dihydropyran-functionalized resin. The procedure has permitted the preparation of several diarylpyridazinones through a Suzuki cross-coupling reaction and cleavage conditions that promoted a retro-ene fragmentation.

Design, synthesis and investigation of new diphenyl substituted pyridazinone derivatives as both cholinesterase and Aβ-aggregation inhibitors

Background: With respect to the increase in the average life expectancy, Alzheimer Disease (AD), the most common form of age-related dementia, has become a major threat to the population over the age of 65 during the past several decades. The majority of AD treatments are focused on cholinergic and amyloid hypotheses. Objective: In this study, three series of diphenyl-2-(2-(4-substitutedpiperazin-1-yl)ethyl)pyridazin- 3(2H)-one derivatives were designed, synthesized and investigated for their ability to inhibit both cholinesterase enzymes and amyloid-β aggregation. Method: The inhibitory activities of the synthesized compounds on AChE (from electric eel) and BChE (from equine serum) were determined by the modified Ellman’s method. The reported thioflavin T-based fluorometric assay was performed to investigate the effect of the selected compounds on the aggregation of Aβ1-42. The cytotoxic effect of the compounds (4g, 11g and 18g) was monitored in 3T3 cell lines to gain insight into therapeutic potential of the compounds by using MTT assay. The crystal structures of the AChE (1EVE) and BChE (1P0I) enzymes were retrieved from the RCSB Protein Data Bank and Molecular Operating Environment (MOE) software was used for molecular docking of the ligands. Results: Among the tested compounds, 5,6-diphenyl derivative 18g was identified as the most potent and selective AChE inhibitor (IC50 = 1.75 μM, Selectivity Index for AChE > 22.857). 4,6- Diphenyl derivative 11g showed the highest and the most selectivity for BChE (IC50= 4.97 μM, SI for AChE 0.124). Interestingly, 4,5-diphenyl derivative 4g presented dual cholinesterase inhibition (AChE IC50= 5.11 μM; BChE IC50= 14.16 μM, SI for AChE = 2.771). Conclusion: Based on biological activity results and low toxicity of the compounds, it can be said that diphenyl substituted pyridazinone core is a valuable scaffold. Especially, dual inhibitory potencies of 4,5-diphenylpyridazin-3(2H)-one core for the cholinesterase enzymes and Aβ- aggregation makes this core a promising disease-modifying agent.

Discovery of a new series of potent prostacyclin receptor agonists with in vivo activity in rat

The design and synthesis of two closely related series of prostacyclin receptor agonist compounds that showed excellent human IP receptor potency and efficacy is described. Compounds from this series showed in vivo activity after SC dosing in the monocrotaline model of PAH in rat.

Pyridazines. Part 36: Synthesis and antiplatelet activity of 5-substituted-6-phenyl-3(2H)-pyridazinones

A convenient and efficient palladium-catalysed retro-ene-assisted method has been developed to prepare a series of 5-substituted-6-phenyl-3(2H)- pyridazinones as potential antiplatelet drugs. The most active compounds were those that contain a 3-phenyl-3-

Pyridazines. Part 30:1 Palladium-catalysed synthesis of 5-substituted 6-phenyl-3(2H)-pyridazinones asissted by a retro-ene transformation

The efficient one-pot functionalization, through palladium-catalysed reactions, of position 5 of the 6-phenyl-3(2H)-pyridazinone system has been performed using a retro-ene-assisted fragmentation. This route allows access through a short synthetic sequenc

Pyridazines. Part 26: Efficient and regioselective Pd-catalysed arylation of 4-bromo-6-chloro-3-phenylpyridazine

The regioselective arylation at position 4 of 4-bromo-6-chloro-3-phenylpyridazine has been performed using a Suzuki cross-coupling reaction. This route allows access to a wide-ranging series of pharmacologically useful pyridazine derivatives and confirms

Pyridazines. Part 25: Efficient and selective deprotection of pharmacologically useful 2-MOM-pyridazinones using Lewis acids

An efficient and selective procedure for the cleavage of a methoxymethyl group at the 2-position in acid-sensitive pyridazinones is presented. Deprotection with Lewis acids (boron tribromide or aluminium chloride) affords 3(2H)-pyridazinones under mild co

Pyridazines part XXIII: Efficient arylation at position 5 of the 6-phenyl-(2H)-pyridazin-3-one system using a Suzuki cross-coupling reaction

A highly efficient procedure for introducing aryl or heteroaryl rings at position 5 of the 6-phenyl-(2H)-pyridazin-3-one system using a Suzuki cross-coupling reaction has been developed in the search for new platelet aggregation inhibitors.