Synthesis of novel 3-pyridinecarbonitriles with amino acid function and their fluorescence properties

Amino Acids. 2004 Mar;26(2):139-46. doi: 10.1007/s00726-003-0051-7. Epub 2003 Dec 31.

Abstract

A variety of N-[(4,6-diaryl-3-pyridinecarbonitrile)-2-yl] amino acid esters 2-4 were synthesized through the reaction of 2-bromo-3-pyridinecarbonitriles 1 with the appropriate alpha-amino acid ester hydrochloride in refluxing dioxane in the presence of triethylamine as dehydrohalogenating agent. Similarly, N'-glycylglycine analogues 5 were obtained through the reaction of 1 with the dipeptide ester. On the other hand, attempts were made towards the construction of amino acid derivatives 7 through the reaction of 1 with aqueous solution alpha-amino acids 6 in refluxing pyridine, but were unsuccessful, and instead the unexpected 2-amino-3-pyridinecarbonitriles 8 were isolated. The fluorescence properties of the newly synthesized pyridines 2-5 were evaluated. Some of the prepared compounds show considerable antibacterial activity.

MeSH terms

  • Amino Acids / chemistry*
  • Candida albicans / drug effects
  • Fluorescence*
  • Gram-Negative Bacteria / drug effects
  • Gram-Positive Bacteria / drug effects
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nitriles / chemical synthesis*
  • Nitriles / chemistry
  • Nitriles / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridines / pharmacology

Substances

  • Amino Acids
  • Nitriles
  • Pyridines