14Dihydropyridine

14dihydropyridine is not a standard term in mainstream chemical nomenclature. In practice, it most often refers to 1,4-dihydropyridine (1,4-DHP), a partially saturated derivative of the pyridine ring. The core features a six-membered ring containing one nitrogen atom and a degree of saturation that renders the ring non-aromatic. Substituents at various positions modify the physical, chemical, and biological properties of the molecule.

1,4-Dihydropyridines are a well-studied class of heterocycles in medicinal chemistry and drug design. They serve as a versatile scaffold for exploring structure–activity relationships and can accommodate diverse aryl, alkyl, and heteroaryl substituents. The 1,4-DHP motif is particularly notable as a pharmacophore in calcium channel blockers, where bulky substituents at selected positions impart selective activity against L-type calcium channels. Clinically used representatives include nifedipine, nimodipine, amlodipine, and felodipine, among others. These drugs are employed to treat hypertension and certain cardiovascular conditions by modulating calcium influx in vascular smooth muscle and cardiac tissue.

Synthesis of 1,4-dihydropyridines is typically accomplished by methods such as the Hantzsch condensation, which combines an aldehyde, a β-ketoester, and ammonia or ammonium acetate to furnish the dihydropyridine core. Alternative routes include hydrogenation of pyridines or multi-component couplings that assemble the ring system in a single step. The chemistry of 1,4-DHPs also extends to redox-active systems and synthetic intermediates for organic and pharmaceutical applications.

Note: when encountered as 14dihydropyridine, the name may be a misnomer or shorthand for 1,4-dihydropyridine derivatives.