1,4-Dihydropyridine: Difference between revisions

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| ImageSizeR1 = 120
| ImageSizeR1 = 120
| ImageAltR1 = Ball-and-stick model of the dihydropyridine molecule
| 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 = USA|date = 27 March 2005|at = Identification and Related Records}}</ref>
| 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
|Section1={{Chembox Identifiers
| CASNo = 3337-17-5
| CASNo = 3337-17-5
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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. 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|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==
==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.
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 pyridines:
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:
:CH<sub>2</sub>(CH=CR)<sub>2</sub>NH → C<sub>5</sub>H<sub>3</sub>R<sub>2</sub>N + H<sub>2</sub>
:CH<sub>2</sub>(CH=CR)<sub>2</sub>NH → C<sub>5</sub>H<sub>3</sub>R<sub>2</sub>N + H<sub>2</sub>
The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:
The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:
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* [[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>
* [[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 receptor]]
* [[Dihydropyridine receptor]]
{{clear}}


==References==
==References==

Latest revision as of 14:31, 7 March 2024

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[edit]

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.[citation needed]

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[edit]

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

References[edit]

  1. ^ "1,4-dihydropyridine - Compound Summary". Pubchem Compound. US: 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 (inactive 2024-03-07).{{cite journal}}: CS1 maint: DOI inactive as of March 2024 (link)
  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[edit]

Retrieved from "https://en.wikipedia.org/w/index.php?title=1,4-Dihydropyridine&oldid=1212372056"