Synthesis and Biological Activities of Ethyl 2-(2-pyridylacetate) Derivatives Containing Thiourea, 1,2,4-triazole, Thiadiazole and Oxadiazole Moieties

Molecules. 2017 Mar 6;22(3):409. doi: 10.3390/molecules22030409.

Abstract

Thirty six novel heterocyclic derivatives of ethyl 2-(2-pyridylacetate) were efficiently synthesized. The new compounds involve the linkage of a 2-pyridyl ring with thiosemicarbazide (compounds 1-7), 1,2,4-triazole (compounds 1a-7a), 1,3,4-thiadiazole (compounds 1b-7b), and 1,3,4-oxadiazole (compounds 1f-7f) moieties. The last group of compounds 1e-7e involves the connection of a 2-pyridyl ring with 1,2,4-triazole and thiourea. ¹H-NMR, 13C-NMR and MS methods were used to confirm the structures of the obtained derivatives. The molecular structures of 3, 3b, 7a and 7f were further confirmed by X-ray crystallography. All obtained compounds were tested in vitro against a number of microorganisms, including Gram-positive cocci, Gram-negative rods and Candida albicans. In addition, the obtained compounds were tested for cytotoxicity and antiviral activity against HIV-1.

Keywords: 1,2,4-triazole; 1,3,4-oxadiazole; 1,3,4-thiadiazole; X-ray crystal structure analysis; biological activity; thiourea.

MeSH terms

  • Anti-Infective Agents / chemical synthesis*
  • Anti-Infective Agents / pharmacology*
  • Bacteria / drug effects
  • Cell Line
  • Cells, Cultured
  • Crystallography, X-Ray
  • Fungi / drug effects
  • HIV-1 / drug effects
  • Humans
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Structure
  • Oxadiazoles / chemistry*
  • Structure-Activity Relationship
  • Thiadiazoles / chemistry*
  • Thiourea / chemistry*
  • Triazoles / chemistry*

Substances

  • Anti-Infective Agents
  • Oxadiazoles
  • Thiadiazoles
  • Triazoles
  • 1,2,4-triazole
  • Thiourea