Microwave-assisted synthesis and in vitro antibacterial activity of novel steroidal thiosemicarbazone derivatives

Bioorg Med Chem Lett. 2012 Dec 15;22(24):7730-4. doi: 10.1016/j.bmcl.2012.09.083. Epub 2012 Oct 11.

Abstract

Herein, we reported the synthesis of 16 novel steroidal thiosemicarbazone derivatives via the condensation of steroidal ketones and substituted thiosemicarbazides under solvent-free conditions using microwave irradiation. The yields obtained are in the range of 84-96% using microwave method and 46-62% using conventional method. All the synthesized compounds (7a-p) have been characterized by (1)H NMR, ESI-MS, IR and elemental analyses. All the series compounds (7a-p) were evaluated for their antibacterial activity against and the results were compared with the standard drug Amoxicillin. Some of the compounds from the series like 7c, 7o and 7p were equipotent with Amoxicillin against Pseudomonas aeruginosa. Also compound 7h was better than Amoxicillin against Staphylococcus aureus and Bacillus subtilis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Bacillus subtilis / drug effects*
  • Dose-Response Relationship, Drug
  • Microbial Sensitivity Tests
  • Microwaves
  • Molecular Structure
  • Pseudomonas aeruginosa / drug effects*
  • Staphylococcus aureus / drug effects*
  • Steroids / chemical synthesis
  • Steroids / chemistry
  • Steroids / pharmacology*
  • Structure-Activity Relationship
  • Thiosemicarbazones / chemical synthesis
  • Thiosemicarbazones / chemistry
  • Thiosemicarbazones / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Steroids
  • Thiosemicarbazones