Efficient synthesis and anti-enteroviral activity of 9-arylpurines

Eur J Med Chem. 2012 Mar:49:279-88. doi: 10.1016/j.ejmech.2012.01.022. Epub 2012 Jan 17.

Abstract

To further explore the anti-enteroviral activity of 9-aryl-6-chloropurines, three different series of compounds with a dialkylamino, (alkyl)amido, or oxazolidinone substituent at the aryl ring have been synthesized, in most cases with the aid of microwave-assisted synthesis. The resulting compounds efficiently inhibit Coxsackie virus type B3 (CVB3) replication with EC(50) values varying from 3 to 15 μM, and with no significant toxicity in Vero cells. The most potent compounds also selectively inhibit the replication of other enteroviruses including Coxsackie virus B4 and Echo virus 11. The cross-resistance studies performed with different 9-aryl-6-chloropurines indicate that they all belong to the same pharmacological family and differ from other CVB3 drugs such as enviroxime.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology*
  • Cell Line
  • Chlorocebus aethiops
  • Enterovirus B, Human / drug effects*
  • Enterovirus Infections / drug therapy
  • Halogenation
  • Humans
  • Microbial Sensitivity Tests
  • Microwaves
  • Models, Molecular
  • Oxazolidinones / chemical synthesis
  • Oxazolidinones / chemistry*
  • Oxazolidinones / pharmacology*
  • Purines / chemical synthesis
  • Purines / chemistry*
  • Purines / pharmacology*
  • Vero Cells

Substances

  • Antiviral Agents
  • Oxazolidinones
  • Purines