title: Synthesis, and cytotoxic and antiplatelet activities of oxime- and methyloxime-containing flavone, isoflavone, and xanthone derivatives.
abstract: A series of oxime- and methyloxime-containing flavone, isoflavone, and xanthone derivatives (1-12) were synthesized (Scheme) and evaluated for their cytotoxic (Table 1) and antiplatelet activities (Table 2). The in vitro anticancer assay indicated that the cytotoxicity of structurally related compounds decreases in the order isoflavones (7a-7c) > flavones (8a-8c) > xanthones (9a-9c), electron-releasing substituents (R) on the Ph ring being favorable (mean GI50 values of 2.84, 12.3, and 20.9 microM for 7c, 8c, and 9c, resp.). The inhibition of platelet aggregation induced by arachidonic acid (AA) similarly decreased from the isoflavone 1 (IC50 = 2.97 microM) to the flavone 2 (7.70 microM) to the xanthone 3 (inactive). Thereby, compound 1 seems to be a promising lead, since it was not only the most-potent aggregation inhibitor (IC50 = 2.97 microM), but was also found to be noncytotoxic at a concentration of 100 microM.
authors.affiliation: Department of Pharmacy, Tajen Institute of Technology, Pingtung 907, Taiwan, Republic of China. tcwang@ccsun.tajen.edu.tw
authors.forename: Tai-Chi
authors.initials: TC
authors.lastname: Wang
authors.forename: I-Li
authors.initials: IL
authors.lastname: Chen
authors.forename: Chai-Ming
authors.initials: CM
authors.lastname: Lu
authors.forename: Daih-Huang
authors.initials: DH
authors.lastname: Kuo
authors.forename: Chang-Hui
authors.initials: CH
authors.lastname: Liao
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D045744:Cell Line, Tumor; D047309:Flavones / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007529:Isoflavones / Q000138:chemical synthesis* / Q000494:pharmacology; D015394:Molecular Structure; D010975:Platelet Aggregation Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D044004:Xanthones / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D047309:Flavones; D007529:Isoflavones; D010975:Platelet Aggregation Inhibitors; D044004:Xanthones