Structure-activity relationships of compounds targeting mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate synthase

Bioorg Med Chem Lett. 2008 Oct 1;18(19):5320-3. doi: 10.1016/j.bmcl.2008.08.034. Epub 2008 Aug 14.

Abstract

We report on a target-based approach to identify possible Mycobacterium tuberculosis DXS inhibitors from the structure of a known transketolase inhibitor. A small focused library of analogs was assembled in order to begin elucidating some meaningful structure-activity relationships of 3-(4-chloro-phenyl)-5-benzyl-4H-pyrazolo[1,5-a]pyrimidin-7-one. Ultimately we found that 2-methyl-3-(4-fluorophenyl)-5-(4-methoxy-phenyl)-4H-pyrazolo[1,5-a]pyrimidin-7-one, although still weak, was able to inhibit M. tuberculosis DXS with an IC(50) of 10.6 microM.

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Combinatorial Chemistry Techniques
  • Drug Design*
  • Inhibitory Concentration 50
  • Molecular Structure
  • Mycobacterium tuberculosis / enzymology*
  • Mycobacterium tuberculosis / genetics
  • Pyrazoles / chemical synthesis*
  • Pyrazoles / chemistry
  • Pyrazoles / pharmacology*
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / chemistry
  • Pyrimidines / pharmacology*
  • Structure-Activity Relationship
  • Transferases / antagonists & inhibitors
  • Transferases / chemistry
  • Transferases / genetics*
  • Transferases / isolation & purification
  • Transferases / metabolism*

Substances

  • 2-methyl-3-(4-fluorophenyl)-5-(4-methoxy-phenyl)-4H-pyrazolo(1,5-a)pyrimidin-7-one
  • Antitubercular Agents
  • Pyrazoles
  • Pyrimidines
  • Transferases
  • deoxyxylulose-5-phosphate synthase