Synthesis of O,O'-Dialkyl-α-phenyl-α-phenylsulfonyloxy-methylphosphonate under Ultrasound and Their Antitumor Activity

doi:10.6023/cjoc201305026

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2226-2231.DOI: 10.6023/cjoc201305026 Previous Articles Next Articles

Notes

超声辐射下O,O'-二烷基-α-取代苯基-α-苯磺酰氧基甲基膦酸酯的合成与生物活性

杨家强^a, 谷晴^a, 胡月维^a, 束波^b, 宋宝安^c, 刘静姿^a

a 遵义医学院药学院遵义 563003;
b 遵义医学院生物化学与分子生物学教研室遵义 563003;
c 贵州大学精细化工研究中心贵阳 550025

收稿日期:2013-05-15 修回日期:2013-06-14 发布日期:2013-07-03
通讯作者: 杨家强 E-mail:yjqcn@126.com
基金资助:
国家自然科学基金(No. 81160385)和贵州省科技厅基金(No. 黔科合J字LKZ[2010]47)资助项目

Synthesis of O,O'-Dialkyl-α-phenyl-α-phenylsulfonyloxy-methylphosphonate under Ultrasound and Their Antitumor Activity

Yang Jiaqiang^a, Gu Qing^a, Hu Yuewei^a, Shu Bo^b, Song Baoan^c, Liu Jingzi^a

a School of Pharmacy, Zunyi Medical College, Zunyi 563003;
b Department of Biochemistry and Molecular Biology, Zunyi Medical College, Zunyi 563003;
c Center for Research and Development of Fine Chemicals, Guizhou University, Guiyang 550025

Received:2013-05-15 Revised:2013-06-14 Published:2013-07-03
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81160385) and the Science and Technology Department of Guizhou Province (No. LKZ[2010]47).

A series of O,O'-dialkyl-α-phenyl-α-phenylsulfonyloxy-methylphosphonates were synthesized from α-hydroxy-phosphonate and benzene sulfonyl chloride under ultrasound. Effects of different solvents, reaction time, reaction temperature and ultrasound power on the yield were investigated. The optimum reaction conditions were obtained. The method has some distinct advantages such as convenient, short reaction time and high yields. Their structures were clearly established by ¹H NMR, IR, MS and elemental analysis, and the fragmentation pathways of them were studied. Preliminary results in bioactivity tests indicated that some title compounds exhibited better activity against A-549.

Key words: α-hydroxyphosphonate, sulfonate, ultrasonic synthesis, antitumor activity

Cite this article

Yang Jiaqiang, Gu Qing, Hu Yuewei, Shu Bo, Song Baoan, Liu Jingzi. Synthesis of O,O'-Dialkyl-α-phenyl-α-phenylsulfonyloxy-methylphosphonate under Ultrasound and Their Antitumor Activity[J]. Chin. J. Org. Chem., 2013, 33(10): 2226-2231.

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超声辐射下O,O'-二烷基-α-取代苯基-α-苯磺酰氧基甲基膦酸酯的合成与生物活性

Synthesis of O,O'-Dialkyl-α-phenyl-α-phenylsulfonyloxy-methylphosphonate under Ultrasound and Their Antitumor Activity

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