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Bioorg Med Chem Lett. 2014 Jul 1;24(13):2839-44. doi: 10.1016/j.bmcl.2014.04.105. Epub 2014 May 5.

Synthesis, cytotoxicity against human oral cancer KB cells and structure-activity relationship studies of trienone analogues of curcuminoids.

Author information

  • 1Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand.
  • 2Division of Physical Science, Faculty of Science and Technology, Huachiew Chalermprakiet University, Samutprakarn 10540, Thailand.
  • 3Department of Chemistry, School of Science, University of Phayao, Phayao 56000, Thailand.
  • 4School of Allied Health Sciences and Public Health, Walailak University, Nakhon Si Thammarat 80160, Thailand.
  • 5Department of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok 10240, Thailand. Electronic address: s_apichart@ru.ac.th.

Abstract

A general method for the synthesis of substituted (1E,4E,6E)-1,7-diphenylhepta-1,4,6-trien-3-ones, based on the aldol condensations of substituted 4-phenylbut-3-en-2-ones and substituted 3-phenylacrylaldehydes, was achieved. The natural trienones 4 and 5 have been synthesized by this method, together with the trienone analogues 9-20. These analogues were evaluated for their cytotoxic activity against human oral cancer KB cell line. The structure-activity relationship study has indicated that the analogues with the 1,4,6-trien-3-one function are more potent than the curcuminoid-type function. Analogues with meta-oxygen function on the aromatic rings are more potent than those in the ortho- and para-positions. Free phenolic hydroxy group is more potent than the corresponding methyl ether analogues. Among the potent trienones, compounds 11, 18 and 20 were more active than the anticancer drug ellipticine. All compounds were also evaluated against the non-cancerous Vero cells and it was found that compounds 11, 12 and 17 were much less toxic than curcumin (1); they showed high selectivity indices of 35.46, 33.46 and 31.68, respectively. These analogues are regarded as the potent trienones for anti-oral cancer study.

Copyright © 2014 Elsevier Ltd. All rights reserved.

KEYWORDS:

Curcuminoid; Cytotoxicity; KB; Synthesis; Trienone analogue

PMID:
24857542
[PubMed - in process]
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