Synthesis, anticonvulsant activity and molecular properties prediction of dialkyl 1-(di(ethoxycarbonyl)methyl)-2,6-dimethyl-4-substituted-1,4-dihydropyridine-3,5-dicarboxylates

Eur J Med Chem. 2014 Feb 12:73:97-104. doi: 10.1016/j.ejmech.2013.12.001. Epub 2013 Dec 12.

Abstract

The synthesis and anticonvulsant properties of new N-diethylmalonyl derivatives of nifedipine and other isosteric analogues (7a-7n) were described. Anticonvulsant screening was performed by subcutaneous pentylenetetrazole (scPTZ) and maximal electroshock (MES) induced seizures tests. Majority of the compounds were effective in scPTZ and MES screens. Compound 7k showed good activity displaying maximum protection, which may be due to the presence of styryl moiety at position 4 of 1,4-dihydropyridine nucleus and the methyl groups of diester functionality. Compounds 7a-7d, 7g, 7i and 7k obeyed the Lipinski's "rule of five" and have drug-likeness. Based on computational prediction of molecular and pharmacokinetic properties, it was found that the compounds have good oral absorption.

Keywords: Diethylmalonyl; Lipinski's “rule of five”; Maximal electroshock method; Pyridine-3,5-dicarboxylates; Subcutaneous pentylenetetrazole method.

MeSH terms

  • Administration, Oral
  • Animals
  • Anticonvulsants / chemical synthesis*
  • Anticonvulsants / chemistry
  • Anticonvulsants / therapeutic use
  • Anticonvulsants / toxicity
  • Dihydropyridines / chemical synthesis*
  • Dihydropyridines / chemistry
  • Dihydropyridines / therapeutic use
  • Dihydropyridines / toxicity
  • Drug Design*
  • Male
  • Mice
  • Molecular Structure
  • Rats
  • Rats, Wistar
  • Seizures / drug therapy
  • Seizures / etiology
  • Structure-Activity Relationship
  • Toxicity Tests, Acute

Substances

  • Anticonvulsants
  • Dihydropyridines