Synthesis and antitrypanosomal activity of new 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles

Bioorg Med Chem Lett. 2012 Dec 1;22(23):7071-4. doi: 10.1016/j.bmcl.2012.09.091. Epub 2012 Oct 2.

Abstract

А series of novel 6,6,7-trisubstituted thiopyrano[2,3-d][1,3]thiazoles-based molecules have been synthesized and evaluated as potential antitrypanosomal agents. The most active analogue 3b inhibited Trypanosoma brucei brucei and Trypanosoma brucei gambiense with an IC(50) of 0.26 and 0.42 μМ, respectively. They could be considered as potent hits for further antitrypanosomal drug discovery efforts.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Humans
  • Pyrans / chemistry*
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology
  • Sulfhydryl Compounds / chemistry*
  • Thiazoles / chemical synthesis
  • Thiazoles / chemistry*
  • Thiazoles / pharmacology
  • Trypanocidal Agents / chemical synthesis*
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / pharmacology
  • Trypanosoma brucei brucei / drug effects
  • Trypanosoma brucei gambiense / drug effects

Substances

  • Pyrans
  • Pyrrolidines
  • Sulfhydryl Compounds
  • Thiazoles
  • Trypanocidal Agents
  • rel-(6'R,7'R)-7'-(3,4-dimethoxyphenyl)-1-(4-chlorophenyl)-3',7'-dihydro-2H,2'H,5H-spiro(pyrolidin-3,6'-thiopyrano(2,3-d)thiazol)-2,2',5-trione
  • thiopyran