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
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