142161-54-4

Basic information

• Product Name: Benzonitrile, 4-(6-methyl-2-pyridinyl)-
• CAS NO: 142161-54-4
• Molecular Formula: C13H10N2
• Molecular Weight: 194.236
• Mol File: 142161-54-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzonitrile, 4-(6-methyl-2-pyridinyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(6-methyl-2-pyridinyl)-(142161-54-4)
• EPA Substance Registry System: Benzonitrile, 4-(6-methyl-2-pyridinyl)-(142161-54-4)

Safety Data

• Hazardous Substances Data: 142161-54-4(Hazardous Substances Data)

Upstream product

• 5315-25-3 2-bromo-6-methylpyridine 
• 18368-57-5 2-mercapto-6-methylpyridine 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 46181-30-0 6-methyl-2-phenylpyridine 
• 142161-37-3 4-(2-Chloro-phenyl)-6-methyl-2-[4-(6-methyl-pyridin-2-yl)-phenyl]-5-(pyridin-2-ylcarbamoyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 

Relevant articles and documents

Bathocuproine-Enabled Nickel-Catalyzed Selective Ullmann Cross-Coupling of Two sp 2-Hybridized Organohalides

Cross-coupling reactions are essential for the synthesis of complex organic molecules. Here, we report a nickel-catalyzed Ullmann cross-coupling of two sp 2-hybridized organohalides, featuring high cross-selectivity when the two coupling partners are used in a 1:1 ratio. The high chemoselectivity is governed by the bathocuproine ligand. Moreover, the mild reductive reaction conditions allow that a wide range of functional groups are compatible in this Ullmann cross-coupling.

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.