74819-19-5

Upstream product

• 5157-08-4 3-methyl-4,5-dihydro-6-oxopyridazine 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 74819-17-3 4-(4-Chloro-benzyl)-6-methyl-pyridazine-3-thiol 
• 74819-14-0 4-p-chlorophenylmethyl-3-chloro-6-methylpyridazine 
• 74819-22-0 4-(4-Chloro-benzyl)-6-methyl-3-methylsulfanyl-pyridazine 
• 74819-27-5 4-p-chlorophenylmethyl-2,6-dimethylpyridazin-3(2H)-one 
• 75256-56-3 [5-(4-Chloro-benzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-acetic acid ethyl ester 
• 75256-58-5 N-Benzyl-2-[5-(4-chloro-benzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-acetamide 
• 75256-59-6 [5-(4-Chloro-benzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-acetic acid hydrazide 
• 75256-57-4 [5-(4-Chloro-benzyl)-3-methyl-6-oxo-6H-pyridazin-1-yl]-acetic acid 

Relevant academic research and scientific papers

6-Methyl-2,4-disubstituted pyridazin-3(2H)-ones: A novel class of small-molecule agonists for formyl peptide receptors

Following a ligand-based drug design approach, a potent mixed formyl peptide receptor 1 (FPR1) and formyl peptide receptor-like 1 (FPRL1) agonist (14a) and a potent and specific FPRL1 agonist (14x) were identified. These compounds belong to a large series of pyridazin-3(2H)-one derivatives substituted with a methyl group at position 6 and a methoxy benzyl at position 4. At position 2, an acetamide side chain is essential for activity. Likewise, the presence of lipophilic and/or electronegative substituents in the position para to the aryl group at the end of the chain plays a critical role for activity. Affinity forFPR1 receptors was evaluated by measuring intracellular calcium flux in HL-60 cells transfected with FPR1, FPRL1, and FPRL2. Agonists were able to activate intracellular calcium mobilization and chemotaxis in human neutrophils. Themost potent chemotactic agent (EC50 =0.6 μM) was the mixed FPR/FPRL1 agonist 14h.

Base-catalysed Condensation of Aromatic Aldehydes with 4,5-Dihydro-6-methylpyridazin-3(2H)-one

4-Arylmethyl-6-methylpyridazin-3(2H)-ones (IIIa-d) have been prepared by the condensation of aromatic aldehydes with 4,5-dihydro-6-methylpyridazin-3(2H)-one (I) in basic media.Compounds IIIa-d react in the lactim form with POCl3 to give 4-arylmethyl-3-chloro-6-methylpyridazines (Va-d), while these react in the lactam form with dimethyl sulphate to give 4-arylmethyl-2,6-dimethylpyridazin-3(2H)-ones (VIa-d).Compound IIId reacts with ethyl bromoacetate in the presence of sodium ethoxide to give the ethyl ester (VIIa) which reacts with benzylamine and hydrazine hydrate togive the corresponding N-benzylamide (VIIc) and hydrazide (VIId).The ester (VIIa) is readily hydrolysed to the corresponding acid (VIIb).