Synthesis and bioactivities of novel thioether/sulfone derivatives containing 1,2,3-thiadiazole and 1,3,4-oxadiazole/thiadiazole moiety

Bioorg Med Chem Lett. 2013 Nov 1;23(21):5821-4. doi: 10.1016/j.bmcl.2013.08.107. Epub 2013 Sep 6.

Abstract

A series of new thioether/sulfone compounds containing 1,2,3-thiadiazole and 1,3,4-oxadiazole/1,3,4-thiadiazole moiety were synthesized, the structures of all products were confirmed by IR, (1)H NMR, (13)C NMR, and element analysis. Preliminary antifungal activity test showed that compound 8a exhibited moderate antifungal activity against Fusarium oxysporum at 50μg/mL. Preliminary antiviral activity results showed that compounds 7a, 7c, 7d, 8a, and 9a displayed high antiviral activity against tobacco mosaic virus. The present work demonstrates that thioether/sulfone heterocyclic derivatives could be considered as new lead compounds for antiviral studies.

Keywords: (1)H NMR; (1)H nuclear magnetic resonance; (13)C NMR; (13)C nuclear magnetic resonance; Antiviral activity; C. mandshurica; Cytospora mandshurica; F. oxysporum; Fusarium oxysporum; G. zeae; Gibberella zeae; Heterocycle; IR; Synthesis; Thioether/sulfone; infra-red spectroscopy.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology
  • Fusariosis / drug therapy
  • Fusarium / drug effects
  • Humans
  • Nicotiana / virology
  • Sulfides / chemical synthesis
  • Sulfides / chemistry*
  • Sulfides / pharmacology
  • Sulfones / chemical synthesis
  • Sulfones / chemistry*
  • Sulfones / pharmacology
  • Thiadiazoles / chemical synthesis
  • Thiadiazoles / chemistry*
  • Thiadiazoles / pharmacology
  • Tobacco Mosaic Virus / drug effects

Substances

  • Antifungal Agents
  • Antiviral Agents
  • Sulfides
  • Sulfones
  • Thiadiazoles
  • 1,3,4-thiadiazole