Synthesis and Antitumor Activity of O,O'-Dialkyl-α-phenyl-α-(substituted benzoylanoxy)-methylphosphonate

doi:10.6023/cjoc201211038

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (05): 1113-1118.DOI: 10.6023/cjoc201211038 Previous Articles Next Articles

Notes

O,O'-二烷基-α-苯基-α-(取代苯甲酰氧基)-甲基膦酸酯的合成与抗肿瘤活性

杨家强^a, 谷晴^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:2012-11-20 修回日期:2012-12-20 发布日期:2013-01-07
通讯作者: 杨家强,yjqcn@126.com 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 and Antitumor Activity of O,O'-Dialkyl-α-phenyl-α-(substituted benzoylanoxy)-methylphosphonate

Yang Jiaqiang^a, Gu Qing^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:2012-11-20 Revised:2012-12-20 Published:2013-01-07
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).

In search of more effective anticancer agents, the title compounds were prepared via the esterification reaction of α-hydroxyphosphonate and substituted bezoic acid with N,N'-dicyclohexylcarbodiimide (DCC) as condensing agent. Twelve of them were reported for the first time. Their structures were clearly established by elemental analysis, IR, ¹H NMR and ¹³C NMR spectra. The antitumor activities of target compounds were tested for the first time. The result indicated that they exhibited certain antitumor activities, and compounds 2i, 2k, 2m showed more potent activities against SGC-7901 with IC₅₀ values of 18.8, 18.5 and 24.5 μmol/L, against A-549 with IC₅₀ values of 24.1, 29.0 and 20.7 μmol/L. Meanwhile, preliminary structure-activity relationships of the title compounds were studied.

Key words: α-hydroxyphosphonate, synthesis, esterification, antitumor activity

Cite this article

Yang Jiaqiang, Gu Qing, Shu Bo, Song Baoan, Liu Jingzi. Synthesis and Antitumor Activity of O,O'-Dialkyl-α-phenyl-α-(substituted benzoylanoxy)-methylphosphonate[J]. Chin. J. Org. Chem., 2013, 33(05): 1113-1118.

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[1] Hudson, H. R.; Yusuf, R. O.; Matthews, R. W. Phosphorus, Sulfur Silicon Relat. Elem. 2008, 83, 1527.
[2] Chen, R.-Y.; Liu, L.-Z. Research of the Organophosphorus Chemistry, Higher Education Press, Beijing, 2001, p. 1 (in Chinese).
(陈茹玉, 刘纶祖, 有机磷化学研究, 高等教育出版社, 北京, 2001, p. 1.)
[3] Delombaert, S.; Erion, M. D.; Tan, J.; Blanchard, L.; Elchehabi, L.; Ghai, R. D.; Sakane, Y.; Berry, C.; Trapani, A. J. J. Med. Chem. 1994, 37, 498.
[4] Wang, W.; Zhang, G.-P.; Song, B.-A.; Wang, H.; Jin, L.-H.; Hu, D.-Y.; Yang, S. Chin. J. Org. Chem. 2007, 26, 279 (in Chinese).
(王伟, 张国平, 宋宝安, 汪华, 金林红, 胡德禹, 杨松, 有机化学, 2007, 26, 279.)
[5] Yang, J.-Q.; Song, B.-A.; Bhadury, P. S.; Chen, Z.; Yang, S.; Cai, X.-J.; Hu, D.-Y.; Xue, W. J Agric. Food Chem. 2010, 58, 2730.
[6] Yang, S.; Gao, X.-W.; Diao, C.-L.; Song, B.-A.; Jin, L.-H.; Xu, G.-F.; Zhang, G.-P.; Wang, W.; Hu, D.-Y.; Xue, W.; Zhou, X.; Lu, P. Chin. J. Chem. 2006, 24, 1581.
[7] Song, B.-A.; Hong, Y.-P.; Jin, L.-H.; Yang, S.; Zou, Z.-H.; Hu, D.-Y.; He, W.; Liu, G.; Zhang, G.-P.; Li, Q.-Z. Chin. J. Org. Chem. 2005, 25, 1001 (in Chinese).
(宋宝安, 洪艳平, 金林红, 杨松, 邹志辉, 胡德禹, 何伟, 刘刚, 张国平, 李黔柱, 有机化学, 2005, 25, 1001.)
[8] Liu, J.-Z.; Song, B.-A.; Fan, H.-T.; Bhadury, P.-S.; Wan, W.-T.; Yang, S.; Xu, W.-M.; Wu, J.; Jin, L.-H.; Xue, W.; Hu, D.-Y.; Zeng, S. Eur. J. Med. Chem. 2010, 45, 5108.
[9] Jin, L.-H.; Song, B.-A.; Zhang, G.-P.; Xu, R.-Q.; Zhang, S.-M.; Gao, X.-W.; Hu, D.-Y.; Yang, S. Bioorg Med. Chem. Lett. 2006, 16, 1537.
[10] Skropeta, D.; Schmidt, R.; Chiral, R. Tetrahedron: Asymmetry 2003, 14, 265.
[11] Fang, H.; Wang, D.-D.; Chen, W.-Z.; Zhao, Y.-F.; Fang, M.-J. Chin. J. Org. Chem. 2010, 30, 1377 (in Chinese).
(方华, 王东冬, 陈伟珠, 赵玉芬, 方美娟, 有机化学, 2010, 30, 1377.)
[12] Zhou, X.-H.; Xu, Q.; Liang, J.; Fu, Z.-H.; Yin, D.-L. Chin. J. Org. Chem. 2012, 32, 393 (in Chinese).
(周晓红, 徐琼, 梁静, 伏再辉, 尹笃林, 有机化学, 2012, 32, 393.)
[13] Agawane, S. M.; Nagarkar, J. M. Tetrahedron Lett. 2011, 52, 3499.
[14] Chou, J.-K.; Liu, G.-S.; Li, J.-P.; Zhao, Y.-L.; Li, H.-J.; Zhang, G.-S. Chin. J. Org. Chem. 2011, 31, 63 (in Chinese).
(仇记宽, 刘国生, 李建平, 赵玉灵, 李会娟, 张贵生, 有机化学, 2011, 31, 63.)
[15] Chen, X.-B.; Shi, D.-Q.; Zhu, X.-F. Chin. J. Chem. 2007, 25, 1854.
[16] Psurski, M.; Oleksyszyn, J.; Blaewska, K.; Gajda, A.; Gajda, T.; Wietrzyk, J. Bioorg. Med. Chem. Lett. 2011, 21, 4572.
[17] Liang, Y.; He, H.-W.; He, H.-F.; Yang, Z.-W. Chin. J. Org. Chem. 2012, 32, 1513 (in Chinese).
(梁英, 贺红武, 何海峰, 杨自文, 有机化学, 2012, 32, 1513.)
[18] Chen, X.-B.; Shi, D.-Q. Phosphorous, Sulfur Silicon Relat. Elem. 2008, 183, 1134.
[19] Pei, Q.; Jin, C.-X.; Niu, M.-L.; Cheng, Z.-H. Chin. J. Org. Chem. 2009, 29, 252 (in Chinese).
(裴强, 金春雪, 牛满丽, 程志红, 有机化学, 2009, 29, 252.)
[20] Sikorshi, J. A.; Miller, M. J.; Walker, M. C. Phosphorous, Sulfur Silicon Relat. Elem. 1993, 76, 115.
[21] Pompliano, D. L.; Rands, E.; Gibbs, J. B. Biochemistry 1992, 31, 3800.
[22] Mccommbit, H.; Sauaders, B. C. J. Chem. Soc. 1945, 67, 380.
[23] Boullet, F. T.; Foucaud, A. Synthesis 1982, 165.

O,O'-二烷基-α-苯基-α-(取代苯甲酰氧基)-甲基膦酸酯的合成与抗肿瘤活性

Synthesis and Antitumor Activity of O,O'-Dialkyl-α-phenyl-α-(substituted benzoylanoxy)-methylphosphonate

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