Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth.

Abstract

Based on the observed anticancer activity of chalcones and retinoids, a novel class of retinoid-chalcone hybrids was designed and synthesized. As part of our ongoing studies to discover natural product based anticancer compounds, the retinoid-chalcone hybrids were tested against the colon cancer cell line HT-29. Retinoid like moiety was introduced through Friedel-Crafts alkylation of toluene. Among the synthesized compounds, the cyano derivative (E)-3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile 8 showed submicromolar inhibitory activity with an IC(50) of 0.66 μM.

• Authors: Cassia S Mizuno, Shiby Paul, Nanjoo Suh, Agnes M Rimando
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 20 Issue 24 Pg. 7385-7 (Dec 15 2010) ISSN: 1464-3405 [Electronic] England
• PMID: 21041085 (Publication Type: Journal Article, Research Support, N.I.H., Extramural, Research Support, Non-U.S. Gov't)
• Copyright: Published by Elsevier Ltd.

Chemical References

• 3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile
• Antineoplastic Agents
• Chalcones
• Retinoids

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, therapeutic use)
• Cell Line, Tumor
• Chalcones (chemical synthesis, chemistry, therapeutic use)
• Colonic Neoplasms (drug therapy)
• Humans
• Retinoids (chemistry)
• Structure-Activity Relationship