Articles

Synthesis and Cytotoxicity of E-Hesperetin Oximes against SGC-7901

  • Liu Zhiping ,
  • Wei Wanxing ,
  • Gan Chunfang ,
  • Huang Yanmin ,
  • Liu Sheng ,
  • Cui Jianguo
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  • a Chemistry and Life Science, Guangxi Teachers Education University, Nanning 530001;
    b College of Chemistry and Chemical Engineer, Guangxi University, Nanning 530004

Received date: 2013-04-12

  Revised date: 2013-05-04

  Online published: 2013-05-13

Supported by

Project supported by the National Natural Science Foundation of China (No. 81060261) and the Natural Science Foundation of Guangxi Province (Nos. 2011GXNSFD018016, 2012GXNSFAA053021)

Abstract

Used natural hesperetin (1) as raw material, persicogenin (2) and 7-O-isopentenyl hesperetin (3) were obtained by the mothod of selective methylation and selective O-prenylation. Nine E-hesperetin oximes 412 were synthesiszed by reaction of 13 with hydroxylamine hydrochloride, methoxylamine hydrochloride and benzyloxygen amine hydrochloride, respectively. Their structures were confirmed by NMR and HR-ESI-MS. The synthesized compounds were evaluated for cytotoxicity against human cancer cell line SGC-7901. The result showed that compounds 46 exhibited dictinct cytotoxicity against SGC-7901.

Cite this article

Liu Zhiping , Wei Wanxing , Gan Chunfang , Huang Yanmin , Liu Sheng , Cui Jianguo . Synthesis and Cytotoxicity of E-Hesperetin Oximes against SGC-7901[J]. Chinese Journal of Organic Chemistry, 2013 , 33(9) : 1970 -1974 . DOI: 10.6023/cjoc201304014

References

[1] Choi, E. M.; Lee, Y. S. Cell. Immunol. 2010, 264, 1.
[2] Zarebczan, B.; Pinchot, S. N.; Kunnimalaiyaan, M.; Chen, H. Am. J. Surg. 2011, 201, 329.
[3] Choi, E. J. Life Sci. 2008, 82, 1059.
[4] Choi, G. S.; Lee, S.; Jeong, T. S.; Lee, M. K.; Lee, J. S.; Jung, U. J.; Kim, H. J.; Park, Y. B.; Bok, S. H.; Choi, M. S. Bioorg. Med. Chem. 2004, 12, 3599.
[5] Shan, Y.; Li, G. Y.; Wang, Q. A.; Li, Z. H. Chin. J. Org. Chem. 2008, 28, 1024 (in Chinese).
(单杨, 李高阳, 汪秋安, 李忠海, 有机化学, 2008, 28, 1024.)
[6] Cai, S. L.; Wu, Z.; Wu, J.; Wang, Q. A.; Shan, Y. Chin. J. Org. Chem. 2012, 32, 560 (in Chinese).
(蔡双莲, 吴峥, 吴进, 汪秋安, 单杨, 有机化学, 2012, 32, 560.)
[7] Wu, Z.; Cai, S. L.; Fan, W. J.; Wang, Q. A. Chin. J. Org. Chem. 2012, 32, 1296 (in Chinese).
(吴峥, 蔡双莲, 范文金, 汪秋安, 有机化学, 2012, 32, 1296.)
[8] Bernini, R.; Mincione, E.; Cortese, M.; Saladino, R.; Gualandi, G.; Belfiore, M. C. Tetrahedron Lett. 2003, 44, 4823.
[9] Ren, J.; Xu, H. J.; Cheng, H; Xin, W. Q.; Chen, Xi.; Hu, K. Eur. J. Med. Chem. 2012, 54, 175.
[10] Chen, I. L.; Chen, J. Y.; Shih, P. C.; Chen, J. J.; Lee, C. H.; Juang, S. H.; Wang, T. C. Bioorg. Med. Chem. 2008, 16, 7639.
[11] Chavi, Y.; Suchana, W.; Pitchuanchom, S.; Sripanidkulchai, B. Arch. Pharm. Res. 2009, 9, 1179.
[12] Chavi, Y.; Suchana, W. Bioorg. Med. Chem. Lett. 2010, 20, 2821.
[13] Chen, C.; Li, X.; Hu, X. F.; Li, Y.; Yin, S. F. Chin. J. Org. Chem. 2011, 31, 1878 (in Chinese).
(陈超, 李霞, 胡晓枫, 李颖, 尹述凡, 有机化学, 2011, 31, 1878.)
[14] Cui, J. G.; Fan, L.; Huang, Y. M.; Xin, Y.; Zhou, A. M. Steroids 2009, 74, 989.
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