Synthesis and biological activity of analogs of CPZEN-45, a novel antituberculosis drug

J Antibiot (Tokyo). 2019 Dec;72(12):970-980. doi: 10.1038/s41429-019-0225-5. Epub 2019 Aug 30.

Abstract

Analogs of CPZEN-45, which is expected to be a promising new antituberculosis drug that overcomes the shortcomings of caprazamycins, were synthesized and their biological activities were evaluated. The biological activity of analogs 1-3, which converted the anilide portion, and analogs 4 and 5, focusing on the seven-membered ring, were lower than that of CPZEN-45. These results suggest that the inhibitory activity of CPZEN-45 against TagO, an ortholog of WecA, has a strict structural limitation, and it was hoped for elucidation of the mode of action of CPZEN-45 using structural biology in the future.

MeSH terms

  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology*
  • Azepines / chemistry*
  • Bacillus subtilis / drug effects
  • Bacillus subtilis / enzymology
  • Bacillus subtilis / genetics
  • Bacterial Proteins / antagonists & inhibitors
  • Bacterial Proteins / genetics
  • Bacterial Proteins / metabolism
  • Escherichia coli Proteins / antagonists & inhibitors
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium / drug effects*
  • Structure-Activity Relationship*
  • Transferases (Other Substituted Phosphate Groups) / antagonists & inhibitors
  • Transferases / antagonists & inhibitors
  • Transferases / genetics
  • Transferases / metabolism

Substances

  • Antitubercular Agents
  • Azepines
  • Bacterial Proteins
  • CPZEN-45
  • Escherichia coli Proteins
  • Transferases
  • Transferases (Other Substituted Phosphate Groups)
  • wecA protein, E coli
  • mraY protein, Bacteria