New bithiazolyl hydrazones: Novel synthesis, characterization and antitubercular evaluation

Bioorg Med Chem Lett. 2017 Jan 15;27(2):288-294. doi: 10.1016/j.bmcl.2016.11.056. Epub 2016 Nov 22.

Abstract

New bithiazolyl hydrazones (6a-l) have been first time synthesized by carrying novel one pot cyclocondensation of 5-acyl thiazoles (1a-b), thiosemicarbazide (2) and substituted phenacyl chlorides (4a-f) in freshly prepared ionic liquid, diisopropyl ethyl ammonium acetate (DIPEAc) at room temperature. The newly synthesized compounds have been evaluated for their antitubercular activity and the compounds 3b, 6a, 6b, 6d, 6e, 6f, 6g, and 6l have displayed noticeable antitubercular activity compared to Rifampicin with tolerable cytotoxicity. All these compounds were also screened for their antibacterial activity and found that, compounds 6j and 6k have exhibited a very good antibacterial activity. Molecular docking study has shown better harmony with the evaluation trend shown by these compounds under in vitro antitubercular screening.

Keywords: Antibacterial activity; Antitubercular activity; Bithiazole; Cytotoxicity; Ionic liquid; Molecular docking; Thiosemicarbazones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antitubercular Agents / chemical synthesis
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Hydrazones / chemical synthesis
  • Hydrazones / chemistry
  • Hydrazones / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Molecular Structure
  • Mycobacterium / drug effects*
  • Mycobacterium bovis / drug effects*
  • Structure-Activity Relationship
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry
  • Thiazoles / pharmacology*

Substances

  • Antitubercular Agents
  • Hydrazones
  • Thiazoles