Synthesis and antiviral bioactivity of novel 3-((2-((1E,4E)-3-oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone derivatives

J Agric Food Chem. 2014 Sep 10;62(36):8928-34. doi: 10.1021/jf502162y. Epub 2014 Aug 25.

Abstract

A series of novel 3-((2-((1E,4E)-3-oxo-5-arylpenta-1,4-dien-1-yl)phenoxy)methyl)-4(3H)-quinazolinone derivatives were designed and synthesized. Antiviral bioassays indicated that a few of the compounds exhibited higher antiviral activities against tobacco mosaic virus (TMV) in vivo than the commercial agent ningnanmycin. In particular, compounds A5, A12, A25, and A27 possessed appreciable curative bioactivities on TMV in vivo, with 50% effective concentration values ranging from 132.25 to 156.10 μg/mL. These values are superior to that of ningnanmycin (281.22 μg/mL) and suggest that novel 4(3H)-quinazolinone derivatives containing 1,4-pentadien-3-one moiety can effectively control TMV. Evaluation of the antiviral properties in field studies and the mechanisms underlying the enhanced antiviral activities of these derivatives are an interesting topic for future investigation.

Keywords: 1,4-pentadien-3-one moiety; 4(3H)-quinazolinone derivatives; antiviral activity; tobacco mosaic virus.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agrochemicals / chemical synthesis*
  • Agrochemicals / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology*
  • Cytidine / analogs & derivatives
  • Cytidine / pharmacology
  • Quinazolinones / chemistry*
  • Structure-Activity Relationship
  • Tobacco Mosaic Virus / drug effects

Substances

  • Agrochemicals
  • Antiviral Agents
  • Quinazolinones
  • ningnanmycin
  • Cytidine
  • 4-hydroxyquinazoline