Synthesis and biological evaluation of 9α- and 9β-hydroxyamino-parthenolides as novel anticancer agents

Bioorg Med Chem Lett. 2014 Aug 15;24(16):4014-8. doi: 10.1016/j.bmcl.2014.06.019. Epub 2014 Jun 14.

Abstract

A series of 9α-hydroxyamino-parthenolides 3-10, 9β-hydroxyamino-parthenolides 11-13 and 9α-hydroxy-1β,10α-epoxyamino-parthenolides 15-19 were efficiently synthesized starting from 9α-hydroxyparthenolide 1 and 9β-hydroxyparthenolide 2, which were isolated from Anvillea radiata. Compounds 1-13 and 15-19 were evaluated for their in vitro anticancer activity by the MTT colorimetric assay against one murine and six human cancer cell lines. This work provides new details about the structural requisites for anticancer activity.

Keywords: 9-Hydroxyamino-parthenolides; 9-Hydroxyparthenolides; 9α-Hydroxy-1β,10α-epoxyamino-parthenolides; 9α-Hydroxy-1β,10α-epoxyparthenolides; Anticancer activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Amines / pharmacology*
  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Humans
  • MCF-7 Cells
  • Mice
  • Molecular Conformation
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / pharmacology*
  • Structure-Activity Relationship

Substances

  • Amines
  • Antineoplastic Agents
  • Sesquiterpenes
  • parthenolide