A new class of potential anti-tuberculosis agents: Synthesis and preliminary evaluation of novel acrylic acid ethyl ester derivatives

Bioorg Med Chem. 2010 Jun 15;18(12):4178-86. doi: 10.1016/j.bmc.2010.05.016. Epub 2010 May 7.

Abstract

Novel acrylic acid ethyl ester derivatives were synthesized and evaluated as potential agents against Mycobacterium species. A versatile and efficient copper-catalyzed coupling process was developed and used to prepare a library of substituted acrylic acid ethyl ester analogs. Minimum inhibitory concentration assays indicated that two of these compounds 3 and 4 have greater in vitro activity against Mycobacterium smegmatis than rifampin, one of the current, first-line anti-mycobacterial chemotherapeutic agents. Moreover, members of this new class of compounds appear to exhibit a specific anti-mycobacterial effect and do not inhibit the growth of the other Gram-positive or Gram-negative species tested.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acrylates / chemical synthesis*
  • Acrylates / chemistry*
  • Acrylates / pharmacology
  • Antitubercular Agents / chemical synthesis*
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / pharmacology
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry
  • Benzothiazoles / pharmacology
  • Catalysis
  • Copper / chemistry
  • Microbial Sensitivity Tests
  • Mycobacterium / drug effects
  • Sulfides / chemical synthesis*
  • Sulfides / chemistry
  • Sulfides / pharmacology

Substances

  • 3-(4-tert-butyl-phenylsulfanyl)acrylic acid ethyl ester
  • 3-(benzothiazol-2-ylsulfanyl)acrylic acid ethyl ester
  • Acrylates
  • Antitubercular Agents
  • Benzothiazoles
  • Sulfides
  • ethyl acrylate
  • Copper