Salicylanilide diethyl phosphates: synthesis, antimicrobial activity and cytotoxicity

Bioorg Med Chem. 2014 Jan 15;22(2):728-37. doi: 10.1016/j.bmc.2013.12.016. Epub 2013 Dec 12.

Abstract

A series of 27 salicylanilide diethyl phosphates was prepared as a part of our on-going search for new antimicrobial active drugs. All compounds exhibited in vitro activity against Mycobacterium tuberculosis, Mycobacterium kansasii and Mycobacterium avium strains, with minimum inhibitory concentration (MIC) values of 0.5-62.5μmol/L. Selected salicylanilide diethyl phosphates also inhibit multidrug-resistant tuberculous strains at the concentration of 1μmol/L. Salicylanilide diethyl phosphates also exhibited mostly the activity against Gram-positive bacteria (MICs ≥1.95μmol/L), whereas their antifungal activity is significantly lower. The IC50 values for Hep G2 cells were within the range of 1.56-33.82μmol/L, but there is no direct correlation with MICs for mycobacteria.

Keywords: Cytotoxicity; Diethyl phosphate; In vitro antimicrobial activity; In vitro antimycobacterial activity; Salicylanilide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Bacteria / drug effects*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Fungi / drug effects*
  • Hep G2 Cells
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Organophosphates / chemical synthesis
  • Organophosphates / chemistry
  • Organophosphates / pharmacology*
  • Salicylanilides / chemical synthesis
  • Salicylanilides / chemistry
  • Salicylanilides / pharmacology*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Antifungal Agents
  • Antineoplastic Agents
  • Organophosphates
  • Salicylanilides