Syntheses of C(18) dibenzocyclooctadiene lignan derivatives as anti-HBsAg and anti-HBeAg agents

Bioorg Med Chem. 2005 Mar 1;13(5):1555-61. doi: 10.1016/j.bmc.2004.12.020.

Abstract

(+)-Gomisin K(3) (1) and kadsurarin (2) were isolated from Schizandra arisanensis and Kadsura matsudai, respectively, and a series of C(18) dibenzocyclooctadiene lignan analogues (5-20) derived from 1 and 2 were synthesized. Esterified derivatives of 1 and 2 were evaluated for inhibitory activity against human type B hepatitis with surface antigen (HBsAg) and e antigen (HBeAg). Most of the analogues (5-8, 10, 12-13) derived from 1 exhibited higher anti-HBsAg effects and lower toxicity, and 6, 7, 8 and 12 also showed higher anti-HBeAg activity. Among these active C(18) dibenzocyclooctadiene lignan analogues, the lignan with a but-3-enoyl group (6) exhibited the most active inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology*
  • Cell Line
  • Hepatitis B Surface Antigens / drug effects*
  • Hepatitis B e Antigens / drug effects*
  • Humans
  • Lignans / chemical synthesis*
  • Lignans / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared

Substances

  • Antiviral Agents
  • Hepatitis B Surface Antigens
  • Hepatitis B e Antigens
  • Lignans