23100-01-8

Basic information

• Product Name: 1-(N-Methylpiperazin-1-yl)-4-phenylphthalazine
• Synonyms: 1-(N-Methylpiperazin-1-yl)-4-phenylphthalazine
• CAS NO: 23100-01-8
• Molecular Weight: 304.395
• Mol File: 23100-01-8.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(N-Methylpiperazin-1-yl)-4-phenylphthalazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(N-Methylpiperazin-1-yl)-4-phenylphthalazine(23100-01-8)
• EPA Substance Registry System: 1-(N-Methylpiperazin-1-yl)-4-phenylphthalazine(23100-01-8)

Safety Data

• Hazardous Substances Data: 23100-01-8(Hazardous Substances Data)

Upstream product

• 5004-45-5 4-phenyl-2H-phthalazin-1-one 
• 4752-10-7 1,4-dichlorophthalazine 
• 109-01-3 1-methyl-piperazine 
• 350690-07-2 4-Chloro-1-(4-methylpiperazin-1-yl)phthalazine 
• 98-80-6 phenylboronic acid 
• 10132-01-1 1-chloro-4-phenyl-phthalazine 

Relevant articles and documents

5-HT3 antagonists derived from aminopyridazine-type muscarinic M1 agonists

A conformational analysis, performed on muscarinic M1 agonists, identified four structural features characteristic of the muscarinic M1 pharmacophore: (i) a protonable basic or quaternary nitrogen acting as a cationic head; (ii) an electronegative dipole usually part of a planar mesomeric ester, amide, or amidine function which can be replaced by an ether (muscarine) or a dioxolane (AF 30); (iii) an intercharge distance of 5 ± 0.5 A? between the cationic head and the electronegative atom of the dipole; (iv) an elevation of 0.5 ± 0.03 A? of the cationic head over the plane containing the electronegative dipole. During a reinvestigation of the conformational behavior of published structures of 5-HT3 antagonists, similar features were observed for the 5-HT3 pharmacophore. However many 5-HT3 antagonists possess additional aromatic planes not present in the muscarinic M1 agonists. These observations brought us to predict the chemical modifications that would change muscarinic M1 agonists into 5-HT3 antagonists. Four of the predicted aminopyridazines were actually synthesized and submitted to testing. The observed IC50 values for 5-HT3 receptor binding ([3H] BRL 43694) ranged from 10 to 425 nM, whereas the affinities for the muscarinic receptor preparations ([2SH] pirenzepine) layed over 10 000 nM. In electrophysiological studies the two most active compounds 10 and 13 produced antagonist-like effects on the 5-HT receptor channel complexes responsible for the generation of the rapidly desensitizing ionic currents, and agonist- like effects on those responsible for the slowly desensitizing components.

Synthesis of 4-aryl-1-(4-methylpiperazin-1-yl)phthalazines by Suzuki-type cross-coupling reaction

Starting from the commercially available 1,4-dichlorophthalazine, a series of 4-aryl-1-(4-methylpiperazin-1-yl)phthalazines was prepared with good yields and under mild conditions by means of a nucleophilic aromatic substitution and a palladium-catalyzed