Synthesis, spectral characterization, and biological activity of some new substituted 10H-phenothiazines, its ribofuranosides, and sulfones

Nucleosides Nucleotides Nucleic Acids. 2010 Mar;29(3):178-89. doi: 10.1080/15257771003708538.

Abstract

This article describes the synthesis of new substituted 10 H-phenothiazines by Smiles rearrangement. These compounds are then used as a base to form ribofuranosides by treating them with a sugar (1-O-acetyl-2,3,5-tri-O-benzoyl-beta-ribofuranose). On oxidation with hydrogen peroxide in glacial acetic acid, these phenothiazines yield their sulfones. These compounds are screened for antioxidant and antimicrobial activity and their structure has been established by elemental analysis and spectroscopic data.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Antioxidants / chemical synthesis
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Candida albicans / drug effects
  • Enterobacter / drug effects
  • Escherichia coli / drug effects
  • Furans / chemical synthesis
  • Furans / chemistry
  • Furans / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Phenothiazines / chemical synthesis*
  • Phenothiazines / chemistry
  • Phenothiazines / pharmacology*
  • Spectrophotometry, Infrared
  • Staphylococcus / drug effects
  • Stereoisomerism
  • Sulfones / chemical synthesis
  • Sulfones / chemistry
  • Sulfones / pharmacology*
  • Time Factors

Substances

  • Anti-Bacterial Agents
  • Antioxidants
  • Furans
  • Phenothiazines
  • Sulfones