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

✍ Scribed by Tai-Chi Wang; I-Li Chen; Daih-Huang Kuo; Chang-Hui Liao

Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
104 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis

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 9__H__‐carbazol‐2‐ol with α‐halocarbonyl reagents, followed by reaction with NH~2~OH or NH~2~OMe (Scheme). A preliminary anticancer assay indicated that the oxime‐type dibenzofuran derivatives 5 and 7a–d 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 IC~50~ value of 14.87 μM, without being cytotoxic at a concentration of 100 μM.

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## Abstract 2‐(Aryloxymethyl)‐5‐benzyloxy‐1‐methyl‐1__H__‐pyridin‐4‐ones **8a**–**8g**, 2‐(aryloxymethyl)‐5‐hydroxy‐4__H__‐pyran‐4‐ones **9a**–**9g**, and 2‐(aryloxymethyl)‐5‐hydroxy‐1‐methyl‐1__H__‐pyridin‐4‐ones **10a**–**10g** were prepared from the known 5‐benzyloxy‐2‐(hydroxymethyl)pyran‐4‐one