Synthesis and structural study of new highly lipophilic 1,4-dihydropyridines?

New Journal of Chemistry Pub Date: 2005-10-26 DOI: 10.1039/B506018D

Abstract

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.

Graphical abstract: Synthesis and structural study of new highly lipophilic 1,4-dihydropyridines
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