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]
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 alsoedit
Chemical structure of Hantzsch's ethyl ester, a well-known dihydropyridine.
^"1,4-dihydropyridine - Compound Summary". Pubchem Compound. US: National Center for Biotechnology Information. 27 March 2005. Identification and Related Records. Retrieved 1 November 2011.
^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)
^Stout, David M.; Meyers, A. I. (1982). "Recent advances in the chemistry of dihydropyridines". Chemical Reviews. 82 (2): 223–243. doi:10.1021/cr00048a004.
^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.
^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.
dihydropyridine, organic, compound, with, formula, parent, compound, uncommon, derivatives, dihydropyridine, important, commercially, biologically, pervasive, cofactors, nadh, nadph, derivatives, dihydropyridine, based, drugs, type, calcium, channel, blockers,. 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 1 4 Dihydropyridine Names Preferred IUPAC name 1 4 Dihydropyridine 1 Identifiers CAS Number 3337 17 5 Y 3D model JSmol Interactive image ChemSpider 94619 Y MeSH 1 4 dihydropyridine PubChem CID 104822 UNII 7M8K3P6I89 Y CompTox Dashboard EPA DTXSID20274185 InChI InChI 1S C5H7N c1 2 4 6 5 3 1 h2 6H 1H2 YKey YNGDWRXWKFWCJY UHFFFAOYSA N Y SMILES C1C CNC C1 Properties Chemical formula C5 H7 N 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 Y verify what is Y N Infobox references Contents 1 Properties and reactions 2 See also 3 References 4 External linksProperties and reactions editA 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 nbsp Chemical structure of Hantzsch s ethyl ester a well known dihydropyridine Dihydropyridine calcium channel blockers Hantzsch ester 5 Dihydropyridine receptorReferences edit 1 4 dihydropyridine Compound Summary Pubchem Compound US National Center for Biotechnology Information 27 March 2005 Identification and Related Records Retrieved 1 November 2011 Duburs Gunars Sausins Alvils 1988 Synthesis of 1 4 Dihydropyridines by Cyclocondensation Reactions Heterocycles 27 269 doi 10 3987 REV 87 370 inactive 2024 03 07 a href Template Cite journal html title Template Cite journal cite journal a CS1 maint DOI inactive as of March 2024 link Stout David M Meyers A I 1982 Recent advances in the chemistry of dihydropyridines Chemical Reviews 82 2 223 243 doi 10 1021 cr00048a004 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 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 editDihydropyridines at the U S National Library of Medicine Medical Subject Headings MeSH Retrieved from https en wikipedia org w index php title 1 4 Dihydropyridine amp oldid 1212372056, wikipedia, wiki, book, books, library,
