Synthesis and evaluation of halogenated 12N-sulfonyl matrinic butanes as potential anti-coxsackievirus agents

Eur J Med Chem. 2017 Jan 27:126:133-142. doi: 10.1016/j.ejmech.2016.09.097. Epub 2016 Sep 30.

Abstract

Twenty-eight new 12N-benzenesulfonyl matrinic butane and halogenated 12N-sulfonyl matrinic butane/ethane derivatives were designed, synthesized and evaluated for their anti-coxsakievirus activities against CVB3 taking compound 1 as the lead. SAR analysis indicated the introduction of a fluoro atom on the 1'-position might be helpful for keeping potency. Among them, compound 8a exhibited potential activities against all CVBs with IC50 ranging from 0.69 to 5.14 μM, suggesting a broad-spectrum anti-coxsackievirus B feature. In addition, it also displayed an excellent PK and a good safety profile, indicating a highly druggable nature. Thus, we consider compound 8a to be a promising drug candidate in the treatment of not only viral myocarditis caused by CVB3 but also various diseases infected with coxsackieviruses B.

Keywords: Coxsakievirus; Druggability; Halogenated matrinic butane; Matrinic butane; structure−activity relationship.

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Antiviral Agents / toxicity
  • Butanes / chemical synthesis*
  • Butanes / chemistry
  • Butanes / pharmacology*
  • Butanes / toxicity
  • Chemistry Techniques, Synthetic
  • Chlorocebus aethiops
  • Drug Design
  • Enterovirus B, Human / drug effects*
  • Halogenation*
  • Structure-Activity Relationship
  • Vero Cells

Substances

  • Antiviral Agents
  • Butanes