Synthesis and evaluation of the antibacterial activities of aryl substituted dihydrotriazine derivatives

Bioorg Med Chem Lett. 2018 May 15;28(9):1657-1662. doi: 10.1016/j.bmcl.2018.03.037. Epub 2018 Mar 16.

Abstract

Five series of dihydrotriazine derivatives containing chalcone (13a-i), phenoxy acetophenone (14a-b), benzyl benzene (15a-c), naphthoxyl acetophenone (16a-b) and benzyl naphthalene (17a-h) moieties were designed and synthesized. The antibacterial and antifungal activities of these compounds were evaluated against several strains of Gram-positive and Gram-negative bacteria, as well as a single fungus. Compound 17h was found to be the most potent of all of the compounds tested, with an MIC value of 0.5 μg/mL against several Gram-positive (Staphylococcus aureus 4220 and QRSA CCARM 3505) and Gram-negative (Escherichia coli 1924) strains of bacteria. However, this compound was inactive against Pseudomonas aeruginosa 2742 and Salmonella typhimurium 2421, indicating that its antibacterial spectrum is similar to those of the positive controls gatifloxacin and moxifloxacin. The cytotoxic activity of the compound 13i, 16b and 17h was assessed in Human normal liver cells.

Keywords: Antibacterial activitis; Antifungal activities; Cytotoxicity; Dihydrotriazine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Cell Line
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Escherichia coli / drug effects*
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation
  • Molecular Structure
  • Pseudomonas aeruginosa / drug effects*
  • Salmonella typhimurium / drug effects*
  • Staphylococcus aureus / drug effects*
  • Structure-Activity Relationship
  • Triazines / chemical synthesis
  • Triazines / chemistry
  • Triazines / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Triazines