Synthesis and structural study of new highly lipophilic 1,4-dihydropyridines
Autor: | Ramón Liz, Merly de Armas, Carlos Seoane, Dolores Molero, Roberto Martínez-Álvarez, Oswald M. Peeters, Amaury Alvarez, Héctor Novoa de Armas, Margarita Suárez, Nazario Martín, Norbert Blaton, Oney Ramirez |
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Rok vydání: | 2005 |
Předmět: | |
Zdroj: | New Journal of Chemistry. 29:1567 |
ISSN: | 1369-9261 1144-0546 |
Popis: | A new series of 1,4-dihydropyridines (1,4-DHPs) endowed with ester groups bearing long and functionalised alkoxy chains at the C3 and C5 positions of the nitrogen ring have been prepared from the corresponding β-keto esters which were in turn prepared by a lipase catalysed transesterification reaction. The structural study has been carried out by X-ray crystallography and theoretical calculations at the semiempirical (AM1), ab initio (HF/6-31G*) and B3LYP/6-31G* levels and reveals that the long alkyl chains do not have any influence on the required geometry of the 1,4-DHPs for biological activity. However, these chains have a strong impact on the lipophilicity and, therefore, they could be used to gain a better control of the duration of the pharmacological action. |
Databáze: | OpenAIRE |
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