Synthesis and Antiproliferative Evaluation of Some Steroidal Oxime Ether

doi:10.6023/cjoc201403047

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (9): 1816-1828.DOI: 10.6023/cjoc201403047 Previous Articles Next Articles

甾体肟醚化合物的合成及抗肿瘤活性研究

黄燕敏^a, 苏绍烊^b, 贾琳怡^c, 甘春芳^a, 林啟福^a, 孔二斌^a, 崔建国^a

a 广西师范学院化学与生命科学学院, 南宁 530001;
b 广西特种设备监督检验院, 南宁 530219;
c 广西南宁市第三十七中南宁 530001

收稿日期:2014-03-22 修回日期:2014-04-21 发布日期:2014-05-07
通讯作者: 崔建国 E-mail:cuijg1954@126.com
基金资助:
广西自然科学基金(No. 2010GXNSFD013019)和广西教育厅重点基金(No. 201202ZD059)资助项目.

Synthesis and Antiproliferative Evaluation of Some Steroidal Oxime Ether

Huang Yanmin^a, Su Shaoyang^b, Jia Linyi^c, Gan Chunfang^a, Lin Qifu^a, Kong Erbin^a, Cui Jianguo^a

a Chemistry and Life Science College, Guangxi Teachers Education University, Nanning 530001;
b Guangxi Special Equipment Supervision and Inspection Institute, Nanning 530026;
c Guangxi Number Thirty-seven Middle School, Naning 530001

Received:2014-03-22 Revised:2014-04-21 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.

Key words: cholesterol, stigmasterol, steroidal oxime ether, antiproliferative activity, bioactivity

Cite this article

Huang Yanmin, Su Shaoyang, Jia Linyi, Gan Chunfang, Lin Qifu, Kong Erbin, Cui Jianguo. Synthesis and Antiproliferative Evaluation of Some Steroidal Oxime Ether[J]. Chin. J. Org. Chem., 2014, 34(9): 1816-1828.

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甾体肟醚化合物的合成及抗肿瘤活性研究

Synthesis and Antiproliferative Evaluation of Some Steroidal Oxime Ether

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