Design, Synthesis, and Bioactivity Evaluation of Novel Isoxazole-Amide Derivatives Containing an Acylhydrazone Moiety as New Active Antiviral Agents

Molecules. 2019 Oct 19;24(20):3766. doi: 10.3390/molecules24203766.

Abstract

As a continuation of our efforts to discover and develop "me-better" active molecules, in this study, a series of novel isoxazole-amide derivatives containing an acylhydrazone moiety were synthesized and evaluated for their antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Antiviral bioassays indicated that some of the target compounds exhibited better in vivo antiviral activities against TMV and CMV than those of Ningnanmycin (NNM). Especially, the compound 7t exhibited the best curative, protection, and inactivation activities against TMV and CMV which were superior to those of NNM. Meanwhile, our present work also revealed that compound 7t could enhance the defense-related enzyme activity and increase the chlorophyll content in tobacco leaves to induce resistance and enhance plant tolerance to TMV infection.

Keywords: acylhydrazone; antiviral activity; isoxazole-amide; synthesis.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Chlorophyll / metabolism
  • Cucumovirus / drug effects
  • Disease Resistance
  • Hydrazones / chemistry*
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Isoxazoles / pharmacology
  • Molecular Structure
  • Nicotiana / metabolism
  • Nicotiana / virology
  • Tobacco Mosaic Virus / drug effects

Substances

  • Antiviral Agents
  • Hydrazones
  • Isoxazoles
  • Chlorophyll