Synthesis and antimetastatic effects of E-salignone amide derivatives

Drug Dev Res. 2014 Mar;75(2):76-87. doi: 10.1002/ddr.21157. Epub 2013 Nov 15.

Abstract

The preparation of novel E-salignone derivatives and their biological evaluation as potential antimetastatic agents is described. The E-salignone amide derivatives were prepared from epiandrosterone and androsterone, and characterized by analytical (1) H NMR, (13) C NMR, and mass spectrometry. The derivatives were evaluated for antimetastatic activity in MDA-MB-231 cells by using a transwell assay. Comparing with the positive control, LY294002, compounds 19b, 19d, and 19e exhibited significant inhibitory effects on the EGF-induced invasion of MB-MDA-231 cells. Moreover, compound 19b also had antimigration effects in wound-healing assay. Compound 19b may represent a novel antimetastatic agent for treating breast cancer.

Keywords: E-salignone; amide derivatives; antimetastasis; breast cancer cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemical synthesis*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Breast Neoplasms / pathology
  • Breast Neoplasms / prevention & control*
  • Cell Movement / drug effects
  • Chromones / pharmacology
  • Female
  • Humans
  • Molecular Structure
  • Morpholines / pharmacology
  • Neoplasm Invasiveness
  • Neoplasm Metastasis
  • Pachysandra / chemistry
  • Pregnenes / chemical synthesis*
  • Pregnenes / chemistry
  • Pregnenes / isolation & purification
  • Pregnenes / pharmacology*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents, Phytogenic
  • Chromones
  • Morpholines
  • Pregnenes
  • 2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one