Hantzsch 1,4-dihydropyridine esters and analogs: candidates for generating reproducible one-dimensional packing motifs

Acta Crystallogr B. 2009 Jun;65(Pt 3):375-81. doi: 10.1107/S0108768109004832. Epub 2009 May 2.

Abstract

Examination of the symmetric Hantzsch 1,4-dihydropyridine ester derivatives of the prototypical nifedipine molecule indicates the tendency of this class of molecule to form a common packing motif. Crystal structure analysis of 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic diesters and analogs reveals that they form extended chains, characterized as the C(6) packing motif, via intermolecular (amine) N-H...O=C (C3,C5 carbonyl) hydrogen bonds. In addition, all the prepared derivatives also satisfy the basic structural requirements for their high binding efficiency to the receptor. The reproducible C(6) packing motif observed among these compounds has a use in the design of solid-state materials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbon / chemistry
  • Crystallography, X-Ray
  • Dihydropyridines / chemistry*
  • Esters / chemistry*
  • Hydrogen Bonding
  • Models, Molecular
  • Molecular Structure

Substances

  • Dihydropyridines
  • Esters
  • Carbon