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Molecules 2014, 19(6), 6911-6928; doi:10.3390/molecules19066911

Synthesis of Novel Lipophilic N-Substituted Norcantharimide Derivatives and Evaluation of Their Anticancer Activities

1
Department of Microbiology, Immunology and Biopharmaceutics, College of Life Sciences, National Chiayi University, Chiayi 60004, Taiwan
2
Laboratory of Biophysics, Department of Medical Research, Taipei Veterans General Hospital, Taipei 11217, Taiwan
3
Department of Radiation Oncology, Mackay Memorial Hospital, New Taipei City 25160, Taiwan
4
Institute of Transitional Medicine, National Yang Ming University, Taipei 11221, Taiwan
5
Department of Biochemical Science and Technology, College of Life Sciences, National Chiayi University, Chiayi 60004, Taiwan
*
Author to whom correspondence should be addressed.
Received: 27 March 2014 / Revised: 21 May 2014 / Accepted: 22 May 2014 / Published: 26 May 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract

This research attempted to study the effect of lipophilicity on the anticancer activity of N-substituted norcantharimide derivatives. Twenty-three compounds were synthesized and their cytotoxicities against five human cancer cell lines studied. The lipophilicity of each derivative was altered by its substituent, an alkyl, alkyloxy, terpenyl or terpenyloxy group at the N-position of norcantharimide. Further, among all synthesized derivatives studied, the compounds N-farnesyloxy-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide (9), and N-farnesyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide (18), have shown the highest cytotoxicity, anti-proliferative and apoptotic effect against human liver carcinoma HepG2 cell lines, yet displayed no significant cytotoxic effect on normal murine embryonic liver BNL CL.2 cells. Their overall performance led us to believe that these two compounds might be potential candidates for anticancer drugs development. View Full-Text
Keywords: norcantharimide derivatives; lipophilic substitution; terpenyl group; anticancer activity; HepG2; apoptosis norcantharimide derivatives; lipophilic substitution; terpenyl group; anticancer activity; HepG2; apoptosis
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MDPI and ACS Style

Wu, J.-Y.; Kuo, C.-D.; Chu, C.-Y.; Chen, M.-S.; Lin, J.-H.; Chen, Y.-J.; Liao, H.-F. Synthesis of Novel Lipophilic N-Substituted Norcantharimide Derivatives and Evaluation of Their Anticancer Activities. Molecules 2014, 19, 6911-6928.

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