1,4-Dihydropyridine: Difference between revisions

{{Chembox

| Watchedfields = changed

| verifiedrevid = 422213266

| ImageFileL1 = 1,4-Dihydropyridine.png

| ImageFileL1_Ref = {{chemboximage|correct|??}}

| ImageSizeL1 = 80

| ImageAltL1 = Skeletal formula of dihydropyridine

| ImageFileR1 = Dihydropyridine-3D-balls.png

| ImageSizeR1 = 120

| ImageAltR1 = Ball-and-stick model of the dihydropyridine molecule

| PIN = 1,4-Dihydropyridine<ref>{{Cite web|title = 1,4-dihydropyridine - Compound Summary|url = https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=104822&loc=ec_rcs|work = Pubchem Compound|publisher = National Center for Biotechnology Information|access-date = 1 November 2011|location = US|date = 27 March 2005|at = Identification and Related Records}}</ref>

|Section1={{Chembox Identifiers

| CASNo = 3337-17-5

| CASNo_Ref = {{cascite|correct|??}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 7M8K3P6I89

| PubChem = 104822

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| MeSHName = 1,4-dihydropyridine

| SMILES = C1C=CNC=C1

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

}}

|Section2={{Chembox Properties

| Formula = {{Chem|C|5|H|7|N}}

| MolarMass = 81.1158 g mol⁻¹

}}

'''1,4-Dihydropyridine''' ('''DHP''') is an [[organic compound]] with the formula CH₂(CH=CH)₂NH. 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|doi-broken-date=2024-03-07 }}</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==

A recurring feature of 1,4-dihydropyridines is the presence of substituents at the 2- and 6-positions. Dihydropyridines are [[enamine]]s, which otherwise tend to tautomerize or hydrolyze.{{cn|date=June 2023}}

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

: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⁻

== Hantzsch ester ==

[[File:HantzschEster.svg|thumb|left|Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine.]]

[[Hantzsch pyridine synthesis|Hantzsch ester]]<ref>{{cite journal |doi=10.1021/ed100171g|title=Rapid and Convenient Synthesis of the 1,4-Dihydropyridine Privileged Structure|year=2010|last1=Cheung|first1=Lawrence L. W.|last2=Styler|first2=Sarah A.|last3=Dicks|first3=Andrew P.|journal=Journal of Chemical Education|volume=87|issue=6|pages=628–630|bibcode=2010JChEd..87..628C}}</ref>

* [[Dihydropyridine calcium channel blockers]]

* [[Ryanodine receptor]]

==References==

{{Reflist}}