1,4-Dihydropyridine: Difference between revisions

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'''1,4-Dihydropyridine''' ('''DHP''') is an [[organic compound]] with the formula CH<sub>2</sub>(CH=CH)<sub>2</sub>NH. Dihydropyridine was first synthesised by Jacob Whalley in his mother's basement as a pure accident. Dr Whalley consumed the agent and suffered from profound hypotension sustaining a fall and permanent brain damage. These profound effects experienced by Dr Whalley then lead Nathan Braithwaite to discover the antihypertensive properties of 1,4-Dihydropyridine. Dr Braithwaite then went on to produce a new antihypertensive calcium channel blocker named Diltiazem. The parent compound is uncommon,<ref>{{cite journal |doi=10.3987/REV-87-370|title=Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions|year=1988|last1=Duburs|first1=Gunãrs|last2=Sausins|first2=Alvils|journal=Heterocycles|volume=27|page=269}}</ref> but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors [[NADH]] and [[NADPH]] are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are [[L-type calcium channel|<small>L</small>-type calcium channel]] blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.<ref>{{cite journal |doi=10.1021/cr00048a004|title=Recent advances in the chemistry of dihydropyridines|year=1982|last1=Stout|first1=David M.|last2=Meyers|first2=A. I.|journal=Chemical Reviews|volume=82|issue=2|pages=223–243}}</ref><ref>{{cite journal |doi=10.1039/B101371H|title=Recent developments in the chemistry of dihydropyridines|year=2002|last1=Lavilla|first1=Rodolfo|journal=Journal of the Chemical Society, Perkin Transactions 1|issue=9|pages=1141–1156}}</ref>
'''1,4-Dihydropyridine''' ('''DHP''') is an [[organic compound]] with the formula CH<sub>2</sub>(CH=CH)<sub>2</sub>NH. The parent compound is uncommon,<ref>{{cite journal |doi=10.3987/REV-87-370|title=Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions|year=1988|last1=Duburs|first1=Gunãrs|last2=Sausins|first2=Alvils|journal=Heterocycles|volume=27|page=269}}</ref> but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors [[NADH]] and [[NADPH]] are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are [[L-type calcium channel|<small>L</small>-type calcium channel]] blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.<ref>{{cite journal |doi=10.1021/cr00048a004|title=Recent advances in the chemistry of dihydropyridines|year=1982|last1=Stout|first1=David M.|last2=Meyers|first2=A. I.|journal=Chemical Reviews|volume=82|issue=2|pages=223–243}}</ref><ref>{{cite journal |doi=10.1039/B101371H|title=Recent developments in the chemistry of dihydropyridines|year=2002|last1=Lavilla|first1=Rodolfo|journal=Journal of the Chemical Society, Perkin Transactions 1|issue=9|pages=1141–1156}}</ref>


==Properties and reactions==
==Properties and reactions==

Revision as of 03:41, 10 September 2021

1,4-Dihydropyridine
Skeletal formula of dihydropyridine
Ball-and-stick model of the dihydropyridine molecule
Names
Preferred IUPAC name
1,4-Dihydropyridine[1]
Identifiers
3D model (JSmol)
ChemSpider
MeSH 1,4-dihydropyridine
UNII
  • InChI=1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2 checkY
    Key: YNGDWRXWKFWCJY-UHFFFAOYSA-N checkY
  • C1C=CNC=C1
Properties
C
5H
7N
Molar mass 81.1158 g mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

1,4-Dihydropyridine (DHP) is an organic compound with the formula CH2(CH=CH)2NH. The parent compound is uncommon,[2] but derivatives of 1,4-dihydropyridine are important commercially and biologically. The pervasive cofactors NADH and NADPH are derivatives of 1,4-dihydropyridine. 1,4-Dihydropyridine-based drugs are L-type calcium channel blockers, used in the treatment of hypertension. 1,2-Dihydropyridines are also known.[3][4]

Properties and reactions

A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines are enamines, which otherwise tend to tautomerize or hydrolyze.

The dominant reaction of dihydropyridines is their ease of oxidation. In the case of dihydropyridines with hydrogen as the substituent on nitrogen, oxidation yields pyridines:

CH2(CH=CR)2NH → C5H3R2N + H2

The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:

CH2(CH=CR)2NR' → C5H3R2NR' + H−

See also

Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine.

References

  1. ^ "1,4-dihydropyridine - Compound Summary". Pubchem Compound. USA: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 1 November 2011.
  2. ^ Duburs, Gunãrs; Sausins, Alvils (1988). "Synthesis of 1,4-Dihydropyridines by Cyclocondensation Reactions". Heterocycles. 27: 269. doi:10.3987/REV-87-370.
  3. ^ Stout, David M.; Meyers, A. I. (1982). "Recent advances in the chemistry of dihydropyridines". Chemical Reviews. 82 (2): 223–243. doi:10.1021/cr00048a004.
  4. ^ Lavilla, Rodolfo (2002). "Recent developments in the chemistry of dihydropyridines". Journal of the Chemical Society, Perkin Transactions 1 (9): 1141–1156. doi:10.1039/B101371H.
  5. ^ Cheung, Lawrence L. W.; Styler, Sarah A.; Dicks, Andrew P. (2010). "Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure". Journal of Chemical Education. 87 (6): 628–630. Bibcode:2010JChEd..87..628C. doi:10.1021/ed100171g.

External links

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