1,4-Dihydropyridine: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
No edit summary
Citation bot (talk | contribs)
Bots
4,929,937 edits
Added doi-broken-date. | Use this bot. Report bugs. | #UCB_CommandLine
 
(43 intermediate revisions by 22 users not shown)
Line 2: Line 2:
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 422213266
| verifiedrevid = 422213266
| ImageFileL1 = Dihydropyridine.png
| ImageFileL1 = 1,4-Dihydropyridine.png
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageSizeL1 = 80
| ImageSizeL1 = 80
Line 9: Line 9:
| ImageSizeR1 = 120
| ImageSizeR1 = 120
| ImageAltR1 = Ball-and-stick model of the dihydropyridine molecule
| ImageAltR1 = Ball-and-stick model of the dihydropyridine molecule
| SystematicName = 1,4-Dihydropyridine<ref>{{Cite web|title = 1,4-dihydropyridine - Compound Summary|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=104822&loc=ec_rcs|work = Pubchem Compound|publisher = National Center for Biotechnology Information|accessdate = 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
| CASNo_Ref = {{cascite|correct|??}}
| CASNo_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 104822
| UNII = 7M8K3P6I89
| PubChem_Ref = {{Pubchemcite|correct|pubchem}}
| ChemSpiderID = 94619
| PubChem = 104822
| ChemSpiderID = 94619
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| MeSHName = 1,4-dihydropyridine
| MeSHName = 1,4-dihydropyridine
| SMILES = C1C=CNC=C1
| StdInChI = 1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2
| SMILES = C1C=CNC=C1
| StdInChI = 1S/C5H7N/c1-2-4-6-5-3-1/h2-6H,1H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = YNGDWRXWKFWCJY-UHFFFAOYSA-N
| StdInChIKey = YNGDWRXWKFWCJY-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| Formula = {{Chem|C|5|H|7|N}}
| Formula = {{Chem|C|5|H|7|N}}
| MolarMass = 81.1158 g mol<sup>−1</sup>
| MolarMass = 81.1158 g mol<sup>−1</sup>
| ExactMass = 81.057849229 g mol<sup>−1</sup>
}}
}}
}}
}}


'''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>
'''Dihydropyridine''' is a molecule based upon [[pyridine]], and the parent of a class of [[molecules]] that have been semi-[[Degree of unsaturation|saturated]] with two [[substituent]]s replacing one [[double bond]]. They are particularly well known in [[pharmacology]] as [[L-type calcium channel|<small>L</small>-type calcium channel]] blockers, used in the treatment of hypertension. Compared with certain other <small>L</small>-type calcium channel blockers (for example those of the [[phenylalkylamine]] class such as [[verapamil]]) which have significant action at the heart, they are relatively vascular selective in their mechanism of action in lowering blood pressure.


==Properties and reactions==
==Class members==
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 <small>L</small>-type calcium channel blockers include, in alphabetical order (brand names vary in different countries): These are derivatives of dihydropyridine.


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:
{| class="wikitable"
: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>
| '''Name''' || '''Image''' || '''Brand name'''
The naturally-occurring dihydropyridines NADH and NADPH contain N-alkyl groups. Therefore, their oxidation does not yield pyridine, but N-alkylpyridinium cations:
|-
:CH<sub>2</sub>(CH=CR)<sub>2</sub>NR' → C<sub>5</sub>H<sub>3</sub>R<sub>2</sub>NR' + H<sup>−</sup>
| [[Amlodipine]] || [[File:Amlodipine.svg|center|195px]] || Norvasc, Istin, Normodipine, Tenox, Cordi Cor
|-
| [[Aranidipine]] || [[File:Aranidipine.svg|center|175px]] || Sapresta (サプレスタ)
|-
| [[Azelnidipine]] || [[File:Azelnidipine structure.svg|center|250px]] || CalBlock (カルブロック)
|-
| [[Barnidipine]] || [[File:Barnidipine structure.svg|center|250px]] || Vasexten, Libradin, Cyress
|-
| [[Benidipine]] || [[File:Benidipine.png|center|150px]] || Coniel
|-
| [[Cilnidipine]] || [[File:Cilnidipine.svg|center|265px]] || Atelec (アテレック), Cilacar
|-
| [[Clevidipine]] || [[File:Clevidipine structure.svg|center|220px]] || Cleviprex
|-
| [[Cronidipine]] || ||
|-
| [[Darodipine]] || [[File:Darodipine.png|center|150px]] ||
|-
| [[Dexniguldipine]] || ||
|-
| [[Efonidipine]] || [[File:Efonidipine.png|center|150px]] ||
|-
| [[Elnadipine]] || ||
|-
| [[Elgodipine]] || ||
|-
| [[Felodipine]] || [[File:Felodipine structure.svg|center|160px]] || Renedil, Plendil
|-
| [[Flordipine]] || ||
|-
| [[Furnidipine]] || ||
|-
| [[Iganidipine]] || ||
|-
| [[Isradipine]] || [[File:Isradipine.svg|center|165px]] || DynaCirc CR
|-
| [[Lacidipine]] || [[File:Lacidipine structure.svg|center|200px]] || Lacipil, Motens, Sakure
|-
| [[Lemildipine]] || ||
|-
| [[Lercanidipine]] || [[File:Lercanidipine.svg|center|267px]] || Zanidip, Zanidip-Recordati
|-
| [[Levamlodipine]] || [[File:Levamlodipine.svg|center|175px]] || EsCordi Cor
|-
| [[Manidipine]] || [[File:Manidipine.svg|center|275px]] || Manyper
|-
| [[Mesuldipine]] || ||
|-
| [[Nicardipine]] || [[File:Nicardipine.svg|center|250px]] || Cardene
|-
| [[Nifedipine]] || [[File:Nifedipine.svg|center|150px]] || Adalat, Nifedical, Procardia, Corinfar, Cordaflex
|-
| [[Niguldipine]] || [[File:Niguldipine.png|center|150px]] ||
|-
| [[Nimodipine]] || [[File:Nimodipine structure.svg|center|215px]] || Nimotop
|-
| [[Niludipine]] || [[File:Niludipine.svg|center|300px]] ||
|-
| [[Nilvadipine]] || [[File:Nilvadipine structure.svg|center|165px]] ||
|-
| [[Nisoldipine]] || [[File:Nisoldipine structure.svg|center|180px]] || Sular
|-
| [[Nitrendipine]] || [[File:Nitrendipine.svg|center|156px]] || Baypress
|-
| [[Olradipine]] || ||
|-
| [[Oxodipine]] || [[File:Oxodipine structure.svg|center|150px]] ||
|-
| [[Palonidipine]] || ||
|-
| [[Pranidipine]] || [[File:Pranidipine.png|center|150px]] ||
|-
| [[Sagandipine]] || ||
|-
| [[Sornidipine]] || ||
|-
| [[Teludipine]] || ||
|-
| [[Tiamdipine]] || ||
|-
| [[Trombodipine]] || ||
|-
| [[Watanidipine]] || ||
|-
|}


==See also==
==See also==
[[File:HantzschEster.svg|thumb|left|Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine.]]
* [[Calcium channel blocker]]
* [[Calcium channel]]
* [[Dihydropyridine calcium channel blockers]]
* [[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==
Line 137: Line 55:
* {{MeshName|Dihydropyridines}}
* {{MeshName|Dihydropyridines}}


{{Calcium channel blockers}}

[[Category:Calcium channel blockers]]
[[Category:Dihydropyridines| ]]
[[Category:Dihydropyridines| ]]

{{Cardiovascular-drug-stub}}
{{Heterocyclic-stub}}

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"