23100-01-8

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 academic research and scientific papers

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.

Microwave-assisted cyclic amidine synthesis using TiCl4

Microwave-assisted treatment of various heterocyclic amides (benzodiazepinone, phthalazone) with TiCl4 in the presence of primary or secondary amines provides the corresponding amidines. In addition to the interest of the microwaves for this re

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