123875-01-4

Basic information

• Product Name: 2-phenylsulfanylethyl methyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-d icarboxylate
• Synonyms: 2-phenylsulfanylethyl methyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-d icarboxylate
• CAS NO: 123875-01-4
• Molecular Formula: C₁₉H₂₃NO₄S
• Molecular Weight: 361.46
• Mol File: 123875-01-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 497.4°Cat760mmHg
• Flash Point: 254.6°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 4.95E-10mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: Desiccate at -20°C
• CAS DataBase Reference: 2-phenylsulfanylethyl methyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-d icarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenylsulfanylethyl methyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-d icarboxylate(123875-01-4)
• EPA Substance Registry System: 2-phenylsulfanylethyl methyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-d icarboxylate(123875-01-4)

Safety Data

• Hazardous Substances Data: 123875-01-4(Hazardous Substances Data)

Usage

Uses

PCA 4248 is a competitive inhibitor of PAF at the PAF-R level.

Biological Activity

A specific PAF antagonist, more potent than the ginkolide BN-52021. Inhibits rabbit platelet aggregation with an IC 50 value of 1.05 μ M and has no significant activity on Ca 2+ channels. Active in vivo , antagonising PAF-induced systemic hypotension and protein-plasma extravasation in rats.

InChI:InChI=1/C19H23NO4S/c1-12-16(18(21)23-4)13(2)20-14(3)17(12)19(22)24-10-11-25-15-8-6-5-7-9-15/h5-9,12,20H,10-11H2,1-4H3

Upstream product

• 141600-64-8 (+)-1,4-dihydro-2,4,6-trimethyl-5-pivaloyloxymethoxycarbonyl-3-pyridinecarboxylic acid 
• 141600-63-7 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylic acid pivaloyloxymethyl ester 
• 141600-97-7 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylic acid 
• 142592-30-1 (-)-2-(phenylthio)ethanol pivaloyloxymethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate 
• 186581-53-3 diazomethane 
• 141600-98-8 (+)-methyl pivaloyloxymethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate 
• 699-12-7 2-(phenylthio)ethanol 
• 141600-70-6 (-)-1,4-dihydro-5-methoxycarbonyl-2,4,6-trimethyl-3-pyridinecarboxylic acid 
• 100303-72-8 2-(phenylthio)ethyl-acetylacetate 
• 21731-17-9 methyl 3-aminocrotonate 
• 75-07-0 acetaldehyde 
• 14205-39-1 methyl (E)-3-aminocrotonate 

Relevant articles and documents

Lipase-catalyzed enantioselective hydrolysis of bis(acyloxymethyl) 1,4- dihydro-3,5-pyridinedicarboxylates leading to optically active medicines

Chiral 4-aryl-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylates and 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate have been obtained in 80-99%ee by lipase catalyzed hydrolysis of bis(acyloxymethyl) 1,4-dihydro- 3,5-pyridinedicarboxylate in an H2O/organic solvent system. These chiral dihydropyridines were readily converted into chiral drugs, such as nicardipine, felodipine and PCA 4248.

Lipase-catalyzed enantioselective hydrolysis of 4-alkyl-1,4-dihydropyridine derivatives: Synthesis of (+) and (-)-methyl 2-(phenylthio)ethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinecarboxylate (PCA 4248)

Asymmetric synthesis of (+)- and (-)-PCA 4248 (PAF antagonist) was achieved using lipase-catalyzed enantioselective hydrolysis of the acyloxymethyl esters. The enzymatic reaction proceeded under the mild conditions in an organic solvent.