Chinese Journal of Organic Chemistry >
Synthesis and Antiproliferative Evaluation of Some Steroidal Oxime Ether
Received date: 2014-03-22
Revised date: 2014-04-21
Online published: 2014-05-07
Supported by
Project supported by the Natural Science Foundation of Guangxi Province (No. 2010GXNSFD013019) and the Natural Science Fund of Education Department of Guangxi Province (No. 201202ZD059).
Oxime ethers display remarkable insecticidal, weeding, antibacterial, antiviral and anticancer physiological activities. Series of steroidal oxime ethers with the structure of 3-, 6- or 22-O-methyloxime or O-benzyloxime were designed and synthesized by different synthetic route using cholesterol or stigmasterol as starting materials. Their structures were characterized by IR, NMR and MS. Antiproliferative activities of the compounds were assayed by thiazolyl blue tetrazolium bromide (MTT) method. Some compounds displayed distinct cytotoxicity against SGC-7901, Bel-7404 and CNE-2 cancer cell lines. Our results reveal that the compounds with the structure of 22-O-methyloxime and 22-O-benzyloxime have better antiproliferative activities. 3β-Hydroxy-22-O-benzyloxime-22,23-secostigmastan-6-thiosemicarbazone (15) displays an excellent antiproliferative activity against CNE-2 cancer cells owning an IC50 value of 5.7 μmol/L.
Huang Yanmin , Su Shaoyang , Jia Linyi , Gan Chunfang , Lin Qifu , Kong Erbin , Cui Jianguo . Synthesis and Antiproliferative Evaluation of Some Steroidal Oxime Ether[J]. Chinese Journal of Organic Chemistry, 2014 , 34(9) : 1816 -1828 . DOI: 10.6023/cjoc201403047
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