Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids

Bioorg Med Chem Lett. 2015 Mar 1;25(5):1021-5. doi: 10.1016/j.bmcl.2015.01.027. Epub 2015 Jan 22.

Abstract

In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.

Keywords: Cancer; Chalcone; Curcuminoids; Invasion; SAR.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Chalcones / chemistry*
  • Chalcones / pharmacology
  • Chickens
  • Curcumin / analogs & derivatives*
  • Curcumin / pharmacology
  • Halogenation
  • Heart / drug effects
  • Humans
  • Neoplasm Invasiveness / pathology
  • Neoplasm Invasiveness / prevention & control*
  • Neoplasms / drug therapy
  • Neoplasms / pathology
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Chalcones
  • Curcumin