Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth.
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.
US Department of Agriculture, Agricultural Research Service, Natural Products Utilization Research Unit, University, MS 38677, USA. cmizuno@olemiss.edu
Cassia S
CS
Mizuno
Shiby
S
Paul
Nanjoo
N
Suh
Agnes M
AM
Rimando
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000627:therapeutic use; D045744:Cell Line, Tumor; D047188:Chalcones / Q000138:chemical synthesis / Q000737:chemistry* / Q000627:therapeutic use; D003110:Colonic Neoplasms / Q000188:drug therapy; D006801:Humans; D012176:Retinoids / Q000737:chemistry*; D013329:Structure-Activity Relationship
C556499:3-(3-oxo-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)prop-1-enyl)benzonitrile; D000970:Antineoplastic Agents; D047188:Chalcones; D012176:Retinoids