| pubmed-article:7636844 | rdf:type | pubmed:Citation | lld:pubmed |
| pubmed-article:7636844 | lifeskim:mentions | umls-concept:C0220781 | lld:lifeskim |
| pubmed-article:7636844 | lifeskim:mentions | umls-concept:C0220825 | lld:lifeskim |
| pubmed-article:7636844 | lifeskim:mentions | umls-concept:C1883254 | lld:lifeskim |
| pubmed-article:7636844 | lifeskim:mentions | umls-concept:C0376211 | lld:lifeskim |
| pubmed-article:7636844 | lifeskim:mentions | umls-concept:C0205464 | lld:lifeskim |
| pubmed-article:7636844 | lifeskim:mentions | umls-concept:C0678594 | lld:lifeskim |
| pubmed-article:7636844 | lifeskim:mentions | umls-concept:C0218561 | lld:lifeskim |
| pubmed-article:7636844 | pubmed:issue | 15 | lld:pubmed |
| pubmed-article:7636844 | pubmed:dateCreated | 1995-9-12 | lld:pubmed |
| pubmed-article:7636844 | pubmed:abstractText | The synthesis and pharmacological activities of the four stereoisomers of methyl tetrahydrofuran-2-ylmethyl 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5- dicarboxylate(furnidipine) are reported. The four isomers were synthesized by a modified Hantzsch synthesis by reaction of (-)- or (+)-tetrahydrofuran-2-ylmethyl 3-aminocrotonate and methyl 2-[(2'-nitrophenyl)methylene]acetoacetate or, alternatively, by reaction of (-)- or (+)-tetrahydrofuran-2-ylmethyl 2-[(2'-nitrophenyl)methylene]acetoacetate and methyl 3-aminocrotonate. The 1:1 diastereomeric mixtures thus obtained were separated by chromatography, using poly(D-phenylglycine) as the chiral stationary phase. The enantiomeric purity of the stereoisomers was determined by a high-performance liquid chromatography-chiral stationary phase technique (HPLC-CSP). Attempts to obtain crystals of a single stereoisomer failed in different solvents, while methanol crystallization of the product obtained from (+/-)-tetrahydrofuran-2-ylmethyl 2-[(2'-nitrophenyl)methylene]acetoacetate and methyl 3-aminocrotonate yielded good-quality crystals of the most insoluble racemate which proved to be a mixture of the (SS)/(RR) enantiomers by X-ray crystallography. Conformational analysis of the stereoisomers, assuming rotation of the aryl substituent and ester groups, shows small energy differences (about 4 kcal.mol-1) between the most and the least favorable conformations. Binding studies were performed using [3H]isradipine as a reference ligand. The results showed stereospecificity of the furnidipine isomers in brain, ileum, and cardiac tissues, the (SS)- and (SR)-isomers clearly being more potent than their (RR)- and (RS)-enantiomers. The (SS)- and (SR)-isomers were also more selective on cerebral tissue when compared with ileal and cardiac preparations. | lld:pubmed |
| pubmed-article:7636844 | pubmed:language | eng | lld:pubmed |
| pubmed-article:7636844 | pubmed:journal | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:7636844 | pubmed:citationSubset | IM | lld:pubmed |
| pubmed-article:7636844 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:7636844 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:7636844 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:7636844 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:7636844 | pubmed:chemical | http://linkedlifedata.com/r... | lld:pubmed |
| pubmed-article:7636844 | pubmed:status | MEDLINE | lld:pubmed |
| pubmed-article:7636844 | pubmed:month | Jul | lld:pubmed |
| pubmed-article:7636844 | pubmed:issn | 0022-2623 | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:PriegoJJ | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:SunkelCC | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:Alvarez-Buill... | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:FonsecaII | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:Fau de... | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:Sanz-Aparicio... | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:PastorMM | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:StatkowP RPR | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:VaqueroJ JJJ | lld:pubmed |
| pubmed-article:7636844 | pubmed:author | pubmed-author:AlajarinRR | lld:pubmed |
| pubmed-article:7636844 | pubmed:issnType | Print | lld:pubmed |
| pubmed-article:7636844 | pubmed:day | 21 | lld:pubmed |
| pubmed-article:7636844 | pubmed:volume | 38 | lld:pubmed |
| pubmed-article:7636844 | pubmed:owner | NLM | lld:pubmed |
| pubmed-article:7636844 | pubmed:authorsComplete | Y | lld:pubmed |
| pubmed-article:7636844 | pubmed:pagination | 2830-41 | lld:pubmed |
| pubmed-article:7636844 | pubmed:dateRevised | 2008-11-21 | lld:pubmed |
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| pubmed-article:7636844 | pubmed:meshHeading | pubmed-meshheading:7636844-... | lld:pubmed |
| pubmed-article:7636844 | pubmed:year | 1995 | lld:pubmed |
| pubmed-article:7636844 | pubmed:articleTitle | Synthesis, structure, and pharmacological evaluation of the stereoisomers of furnidipine. | lld:pubmed |
| pubmed-article:7636844 | pubmed:affiliation | Departamento de Química Orgánica, Universidad de Alcalá, Madrid, Spain. | lld:pubmed |
| pubmed-article:7636844 | pubmed:publicationType | Journal Article | lld:pubmed |
| pubmed-article:7636844 | pubmed:publicationType | In Vitro | lld:pubmed |
| pubmed-article:7636844 | pubmed:publicationType | Research Support, Non-U.S. Gov't | lld:pubmed |
| http://linkedlifedata.com/r... | http://linkedlifedata.com/r... | pubmed-article:7636844 | lld:chembl |
