Synthesis of heterocycle-attached methylidenebenzenesulfonohydrazones as antifungal agents

Bioorg Med Chem Lett. 2015 Nov 15;25(22):5092-6. doi: 10.1016/j.bmcl.2015.10.017. Epub 2015 Oct 13.

Abstract

A series of heterocycle-attached methylidenebenzenesulfonohydrazone derivatives were synthesized and evaluated for their antifungal activities against seven phytopathogenic fungi such as Fusarium graminearum, Alternaria solani, Valsa mali, Phytophthora capsici, Fusarium solani, Botrytis cinerea, and Glomerella cingulata. Compounds 7b, 8d, 9a, 9b and 9d exhibited a good and broad-spectrum of antifungal activities against at least five phytopathogenic fungi at the concentration of 100 μg/mL. It demonstrated that addition of one double bond between the phenylsulfonylhydrazone fragment and the furan ring of 6a,b,d could afford more active compounds 9a,b,d; however, introduction of the nitro group on the phenyl ring of 6a-9a gave less potent compounds 6e-9e.

Keywords: Antifungal activity; Hybrids; Phenylsulfonylhydrazone; Phytopathogenic fungi; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alternaria / drug effects
  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / pharmacology*
  • Botrytis / drug effects
  • Fusarium / drug effects
  • Hydrazones / chemical synthesis
  • Hydrazones / pharmacology*
  • Oxazoles / pharmacology
  • Phyllachorales / drug effects
  • Phytophthora / drug effects
  • Sulfonamides / chemical synthesis
  • Sulfonamides / pharmacology*

Substances

  • Antifungal Agents
  • Hydrazones
  • Oxazoles
  • Sulfonamides
  • hymexazol