Application of "hydrogen bonding interaction" in new drug development: design, synthesis, antiviral activity, and SARs of thiourea derivatives

J Agric Food Chem. 2015 Feb 11;63(5):1378-84. doi: 10.1021/jf505355r. Epub 2015 Feb 3.

Abstract

A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 μg/mL and 39%/100 μg/mL; inactivation activity, 71%/500 μg/mL and 35%/100 μg/mL; curative activity, 73%/500 μg/mL and 37%/100 μg/mL; protection activity, 69%/500 μg/mL and 33%/100 μg/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.

Keywords: SARs; anti-TMV activity; nature product; thiourea derivatives; tobacco mosaic virus.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Drug Design
  • Hydrogen Bonding
  • Nicotiana / virology
  • Plant Diseases / virology
  • Structure-Activity Relationship
  • Thiourea / chemistry*
  • Tobacco Mosaic Virus / drug effects

Substances

  • Antiviral Agents
  • Thiourea