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- Title
Synthesis and Cytotoxic and Antiplatelet Activities of Dibenzofuran- and Carbazole-Substituted Oximes.
- Authors
Tai-Chi Wang; I-Li Chen; Daih-Huang Kuo; Chang-Hui Liao
- Abstract
The dibenzofuran- and carbazole-substituted oximes or methyloximes 510 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 7ad are active, while the corresponding oxime ethers 9b 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.
- Subjects
DIBENZOFURANS; ANTINEOPLASTIC agents; OXIMES; ALKYLATION
- Publication
Helvetica Chimica Acta, 2004, Vol 87, Issue 4, p983
- ISSN
0018-019X
- Publication type
Article