122956-89-2

Basic information

• Product Name: 4-(2-Chloro-phenyl)-6-methyl-2-[4-(4-methyl-imidazol-1-yl)-phenyl]-5-(pyridin-2-ylcarbamoyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester
• CAS NO: 122956-89-2
• Molecular Weight: 554.048
• Mol File: 122956-89-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-(2-Chloro-phenyl)-6-methyl-2-[4-(4-methyl-imidazol-1-yl)-phenyl]-5-(pyridin-2-ylcarbamoyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-Chloro-phenyl)-6-methyl-2-[4-(4-methyl-imidazol-1-yl)-phenyl]-5-(pyridin-2-ylcarbamoyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester(122956-89-2)
• EPA Substance Registry System: 4-(2-Chloro-phenyl)-6-methyl-2-[4-(4-methyl-imidazol-1-yl)-phenyl]-5-(pyridin-2-ylcarbamoyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester(122956-89-2)

Safety Data

• Hazardous Substances Data: 122956-89-2(Hazardous Substances Data)

Upstream product

• 142161-53-3 4'-(4-methylimidazol-1-yl)acetophenone 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 89-98-5 2-chloro-benzaldehyde 
• 60155-47-7 N-(2-pyridyl)-3-aminocrotonamide 
• 142161-48-6 ethyl <4'-(4-methylimidazol-1-yl)benzoyl>acetate 

Relevant articles and documents

1,4-Dihydropyridines as Antagonists of Platelet Activating Factor. 1. Synthesis and Structure-Activity Relationships of 2-(4-Heterocyclyl)phenyl Derivatives

A novel class of 2-(4-heterocyclylphenyl)-1,4-dihydropyridines (2-38) possessing antagonist activity against platelet activating factor (PAF) was prepared by the Hantzsch synthesis from a variety of ethyl 4'-heterocyclic-substituted benzoylacetates, aryl or heteroaryl aldehydes, and substituted 3-aminocrotonamides or 3-aminocrotonate esters.Structure-activity relationships were evaluated where PAF antagonist activity was measured in vitro by determining the concentration of compound (IC50) required to inhibit the PAF-induced aggregation of rabbit washed platelets,and in vivo by determining the oral dose (ED50) which protected mice from a lethal injection of PAF.The nature of the substituent at the dihydropyridine 2-position was found to be important for both in vitro and in vivo activity, whereas there was greater flexibility for structural variation at the 4- and 5-positions.The most potent compound was 4-(2-chlorophenyl)-1,4-dihydro-3-(ethoxycarbonyl)-6-methyl-2-pyrid-1-yl)phenyl>-5-pyridine (17, UK-74,505), IC50 = 4.3 nM, ED50 = 0.26 mg/kg po, which was found to be approximately 33 times more potent in vitro (rabbit platelet aggregation) and about 8 times more potent in vivo (murine lethality) than WEB2086.Compound 17 also exhibited a long duration of action in the dog (inhibition of PAF-induced whole blood aggregation ex vivo was maintained for > 24 h following a single oral dose of 75 μg/kg) and was highly selective as a PAF antagonist, showing only weak affinity (IC50 = 6600 nM) for the nitrendipine binding site.As a result of its high oral potency, selectivity, and duration of action, UK-74,505 has been selected for clinical evaluation.