Synthesis and Cytotoxic and Antiplatelet Activities of Dibenzofuran- and Carbazole-Substituted Oximes

Tai Chi Wang*, I. Li Chen, Daih Huang Kuo, Chang Hui Liao

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

11 Scopus citations

Abstract

The dibenzofuran- and carbazole-substituted oximes or methyloximes 5-10 were prepared and evaluated for their cytotoxic and antiplatelet activities. These compounds were synthesized via alkylation of dibenzofuran-2-ol or 9H-carbazol-2-ol with α-halocarbonyl reagents, followed by reaction with NH2OH or NH2OMe (Scheme). A preliminary anticancer assay indicated that the oxime-type dibenzofuran derivatives 5 and 7a-d are active, while the corresponding oxime ethers 9h and 9c are inactive at the same concentration. Therefore, a H-bond-donating group seems to be crucial for cytotoxicity. Among the compounds tested, 2-[(dibenzo[b,d]-furan-2-yl)oxy]-1-(4-methoxyphenyl)ethan-1-one O-methyloxime (9c) exhibited potent inhibitory activity against platelet aggregation induced by arachidonic acid, with an IC50 value of 14.87 μM, without being cytotoxic at a concentration of 100 μM.

Original languageEnglish
Pages (from-to)983-990
Number of pages8
JournalHelvetica Chimica Acta
Volume87
Issue number4
DOIs
StatePublished - 2004

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