TY - JOUR
T1 - Synthesis and Cytotoxic and Antiplatelet Activities of Dibenzofuran- and Carbazole-Substituted Oximes
AU - Wang, Tai Chi
AU - Chen, I. Li
AU - Kuo, Daih Huang
AU - Liao, Chang Hui
PY - 2004
Y1 - 2004
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=2342640048&partnerID=8YFLogxK
U2 - 10.1002/hlca.200490091
DO - 10.1002/hlca.200490091
M3 - 文章
AN - SCOPUS:2342640048
SN - 0018-019X
VL - 87
SP - 983
EP - 990
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 4
ER -