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  • Title: Synthesis of chiral hydroxylated enones as potential anti-tumor agents.
    Author: Shing TK, Wu HT, Kwok HF, Lau CB.
    Journal: Bioorg Med Chem Lett; 2012 Dec 15; 22(24):7562-5. PubMed ID: 23102892.
    Abstract:
    A series of chiral hydroxylated enones were synthesized as COTC ether analogues to investigate the structural features required for optimal and selective anti-tumor activity. The cytotoxicity of the seven COTC ether analogues against WRL-68 normal and HepG2, HL-60 cancer cell lines were measured. C-4 ether analogues with an aliphatic chain substituent were found to be more favorable than their aromatic counterparts. Inversion of the configuration at C-4 in 5e to give 5f only resulted in reduced selectivity towards cancer cells. These results show that 4-O-pentyl-gabosine D (5e) has optimum selectivity and cytotoxicity towards two cancer cell lines.
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