121497-05-0

Basic information

• Product Name: dimethyl 4-[4-(methoxycarbonyl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• Synonyms: 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-4-(4-(methoxycarbonyl)phenyl)-2,6-dimethyl-, dimethyl ester; 3,5-pyridinedicarboxylic acid, 1,4-dihydro-4-[4-(methoxycarbonyl)phenyl]-2,6-dimethyl-, dimethyl ester; Dimethyl 4-[4-(methoxycarbonyl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS NO: 121497-05-0
• Molecular Formula: C₁₉H₂₁NO₆
• Molecular Weight: 359.3731
• Mol File: 121497-05-0.mol

Chemical Properties

• Boiling Point: 487.4°C at 760 mmHg
• Flash Point: 248.6°C
• Density: 1.204g/cm³
• Vapor Pressure: 1.19E-09mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: dimethyl 4-[4-(methoxycarbonyl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl 4-[4-(methoxycarbonyl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate(121497-05-0)
• EPA Substance Registry System: dimethyl 4-[4-(methoxycarbonyl)phenyl]-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate(121497-05-0)

Safety Data

• Hazardous Substances Data: 121497-05-0(Hazardous Substances Data)

Upstream product

• 1571-08-0 methyl 4-formylbenzoate 
• 14205-39-1 methyl 3-aminocrotonate 
• 67-56-1 methanol 
• 619-66-9 4-Carboxybenzaldehyde 
• 105-45-3 acetoacetic acid methyl ester 

Relevant articles and documents

The Hantzsch reaction for nitrogen-13 PET: Preparation of [13N]nifedipine and derivatives

Nitrogen-13 is an attractive but under-used PET radionuclide for labelling molecules of biological and pharmaceutical interest, complementing other PET radionuclides. Its short half-life (t1/2 = 9.97 min) imposes synthetic challenges, but we have expanded the hitherto limited pool of 13N labelling strategies and tracers by adapting the multicomponent Hantzsch condensation reaction to prepare a library of 13N-labelled 1,4-dihydropyridines from [13N]ammonia, including the widely-used drug nifedipine. This represents a key advance in 13N PET radiochemistry, and will serve to underpin the renewed interest in clinical opportunities offered by short-lived PET tracers.

Ionic liquid phase technology supported the three component synthesis of Hantzsch 1,4-dihydropyridines and Biginelli 3,4-dihydropyrimidin-2(1H)-ones under microwave dielectric heating

A microwave dielectric heating assisted liquid phase synthesis of 1,4-dihydropyridines, 3,4-dihydropyrimidin-2(1H)-ones, pyridines and polyhydroquinolines using task-specific ionic liquid as a soluble support was described. The efficiency of the ionic liquid phase organic synthesis (IoLiPOS) methodology was demonstrated by using a one-pot three component condensation. The structure of the intermediates in each step was verified routinely by spectroscopic analysis and, after cleavage the target compounds were obtained in good yields and high purities.

Syntheses and bioevaluation of substituted dihydropyridines for pregnancy-interceptive activity in hamsters

A number of 2,6-dimethyl-3,5-bis(methoxycarbonyl)-4-substituted-1,4-dihydropyridines were synthesized and evaluated for pregnancy-interceptive activity in mated hamsters. Our of 24 compounds, 12, 15, 21, 22, 28, and 34 caused a marked reduction in the number of implantations when administered on days 3-8 postcoitum. In an in vitro competition assay, none of the compounds exhibited noticeable binding affinity for uterine progesterone receptors. The results reported here have helped to identify new leads for developing pregnancy-interceptive agents and the active compounds do not seem to elicit their interceptive effect through receptor-mediated inhibition of progesterone action in hamster uterus.