Preparation and anti-HIV activities of retrojusticidin B analogs and azalignans

Bioorg Med Chem. 2004 Aug 1;12(15):4045-54. doi: 10.1016/j.bmc.2004.05.036.

Abstract

Ten lignans (2-11) and a series of azalignans including 1-aryl-pyrronaphthalenes 20-24 and 3-N-alkylaminomethyl-1-arylnaphthalenes 25-28, structurally related to two HIV reverse transcriptase inhibitors, retrojusticidin B and phyllamyricin A, were prepared from phyllanthin (1) for evaluation of anti-HIV activities. Anti-HIV activity of these compounds on a R5 pseudotype virus, ConB/pNL43E-L+, in the U87-CD4-CCR5 cells has been measured. Compounds 5, 22, 23, and 28 showed good anti-HIV activity with IC(50) value of 0.25, 1.07, 0.01, 0.32 microg/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / pharmacology*
  • Biological Assay
  • Cell Line
  • Cell Survival / drug effects
  • HIV-1 / drug effects*
  • Humans
  • Lignans / chemical synthesis*
  • Lignans / pharmacology*
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / pharmacology*

Substances

  • Anti-HIV Agents
  • Lignans
  • Naphthalenes
  • phyllamyricin A
  • retrojusticidin B