Synthesis of polyhydroxylated aromatics having amidation of piperazine nitrogen as HIV-1 integrase inhibitor

Bioorg Med Chem Lett. 2010 Sep 15;20(18):5469-71. doi: 10.1016/j.bmcl.2010.07.087. Epub 2010 Jul 25.

Abstract

(E)-N-[3-(4-cinnamoylpiperazin-1-yl)propyl]-3,4-dihydroxybenzamide and (E)-N-[3-(4-cinnamoylpiperazin-1-yl)propyl]-3,4,5-trihydroxybenzamide were designed and synthesized as potential HIV-1 integrase inhibitors and evaluated their inhibition to the strand transfer process of HIV-1 integrase. The result indicates that 3,4,5-trihydroxylated aromatic derivatives exhibit good inhibition to HIV-1 integrase, however, corresponding 3,4-dihydroxylated aromatic derivatives appear little inhibition of HIV-1 integrase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • HIV Infections / drug therapy
  • HIV Infections / enzymology*
  • HIV Integrase / metabolism*
  • HIV Integrase Inhibitors / chemical synthesis
  • HIV Integrase Inhibitors / chemistry*
  • HIV Integrase Inhibitors / pharmacology*
  • HIV-1 / drug effects
  • HIV-1 / enzymology*
  • Humans
  • Piperazine
  • Piperazines / chemical synthesis
  • Piperazines / chemistry*
  • Piperazines / pharmacology*
  • Structure-Activity Relationship

Substances

  • HIV Integrase Inhibitors
  • Piperazines
  • Piperazine
  • HIV Integrase