1,4-dihydropyridine

from Wikipedia, the free encyclopedia
Structural formula
Structure of dihydropyridine
General
Surname 1,4-dihydropyridine
other names

Dihydropyridine

Molecular formula C 5 H 7 N
External identifiers / databases
CAS number 3337-17-5
PubChem 104822
Wikidata Q39094
properties
Molar mass 81.12 g mol −1
Physical state

liquid

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dihydropyridine is a chemical compound consisting of a six-membered unsaturated ring with one nitrogen atom. It forms the basic structure of the dihydropyridines , which are used in medicine as calcium channel blockers in arterial hypertension . Its unsaturated analogue is pyridine .

presentation

The reduction of pyridine using lithium aluminum hydride gives a mixture of 1,4-dihydropyridine, 1,2-dihydropyridine and 2,5-dihydropyridine . Pure 1,4-dihydropyridine is formed from pyridine in the presence of organic magnesium and zinc complexes.

The dihydropyridine synthesis according to Arthur Hantzsch is used to prepare more highly substituted pyridines .

Biological importance

Dihydropyridine derivatives (e.g. the lead substance nifedipine , amlodipine , isradipine , nitrendipine , nimodipine or felodipine ) can block the voltage-dependent L-type calcium channel , i.e. act as antagonists. Before the exact function of this channel was explained, it was therefore called the dihydropyridine receptor .

Individual evidence

  1. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  2. ↑ DD Tanner, Yang, C.-M .: On the structure and mechanism of formation of the Lansbury reagent, lithium tetrakis (N-dihydropyridyl) aluminate , in J. Org. Chem. , 1993 , 58 , 1840-1846 doi : 10.1021 / jo00059a041 .
  3. ^ DM Stout, AI Meyers: Recent advances in the chemistry of dihydropyridines , in Chem. Rev. , 1982 , 82 , 223-243 doi : 10.1021 / cr00048a004 .
  4. ↑ AJ De Koning, PHM Budzelaar, J. Boersma, GJM van der Kerk: Specific and selective reduction of aromatic nitrogen heterocycles with the bis-pyridine complexes of bis (1,4-dihydro-1-pyridyl) zinc and bis (1, 4-dihydro-1-pyridyl) magnesium , in J. Organomet. Chem. , 1980 , 199 , 153-170 doi : 10.1016 / S0022-328X (00) 83849-8 .
  5. ↑ Joachim Buddrus: Fundamentals of organic chemistry . 3rd edition, 2003, p. 360.