SIOC English
有机化学
高级检索

有机化学 >

2014 , Vol. 34 >Issue 8: 1609 - 1615

DOI: https://doi.org/10.6023/cjoc201402013

研究论文

7（6）-羟基黄酮衍生物的合成及初步抗肿瘤活性研究

  • 王学军 ,
  • 刘建利
展开
  • a 陕西省商洛学院生物医药工程系 商洛 726000;
    b 西部资源生物与现代生物技术省部共建教育部重点实验室 西安 710069

收稿日期: 2014-02-11

  修回日期: 2014-03-25

  网络出版日期: 2014-04-18

基金资助

国家自然科学基金（Nos.20872118，30070905）、陕西省自然科学基金（No.2014JM4097）、陕西省教育厅基金（No.2013JK0836）、商洛学院人才引进基金（No.13sky0035）资助项目.

收起

Synthesis and Preliminary Antitumor Activities of 7(6)-Hydroxylflavone Derivatives

  • Wang Xuejun ,
  • Liu Jianli
Expand
  • aDepartment of Biomedical Engineering, Shangluo University, Shangluo 726000;
    b Key Laboratory of Resource Biology and Biotechnology in Western China, Ministry of Education, School of Life Science, Northwest University, Xi'an 710069

Received date: 2014-02-11

  Revised date: 2014-03-25

  Online published: 2014-04-18

Supported by

Project supported by the National Natural Science Fundation of China (Nos. 20872118, 30070905), the Natural Science Fundation of Shaanxi Province (No. 2014JM4097), the Foundation of the Education Department of Shaanxi Province (No. 2013JK0836) and the Talent Introduction Foundation of Shangluo University (No. 13sky0035).

Fold

摘要

以间苯二酚和对苯二酚为起始原料，经过傅克酰化、Baker-Venkataraman重排、关环三步反应分别得到5个7-羟基黄酮和5个6-羟基黄酮类化合物. 试验结果发现，这些化合物溶解性能不好，生物活性不高，因此，对这些化合物又经过苯甲酰化并将7-羟基黄酮与1-氯-3-溴丙烷首先发生亲核取代反应，然后和诺氟沙星在丙酮中反应生成化合物13，总共得到了5个结构新颖的黄酮和4个未见文献报道的β-丙二酮类化合物. 通过四甲基偶氮唑盐（MTT）法对19个化合物的抑制人宫颈癌细胞 Hela活性进行了体外评价，结果表明：化合物13的半数抑制浓度IC50为19.4 μmol/L，具有深入研究的价值.

关键词： 7（6）-羟基黄酮; 衍生物; 合成; 抗肿瘤活性

本文引用格式

王学军 , 刘建利 . 7（6）-羟基黄酮衍生物的合成及初步抗肿瘤活性研究[J]. 有机化学, 2014 , 34(8) : 1609 -1615 . DOI: 10.6023/cjoc201402013

Abstract

Five 7-hydroxylflavones and five 6-hydroxylflavones have been synthesized with resorcinol and paradioxybenzene as starting materials in three steps by an improved Baker-Venkatarama rearrangement reaction. Experimental results showed that the ten compounds have poor solubility in methanol and chloroform solvent and low biological activity. Therefore, some of these compounds are further derivatived and five new compounds were successfully synthesized. The nineteen compounds, including four new β-propenediones 4b, 4c, 4d and 4e, were evaluated for antitumor activities against hela human cervical carcinoma cell lines by methyl thiazolyl tetrazolium (MTT) method. The preliminary biological activity tests showed that compound 13 exhibited potentially high activity against hela human cervical carcinoma cell lines with IC50 value of 19.4 μmol/L.

Key words： 7(6)-hydroxyflavone; derivative; synthesis; antitumor activity

参考文献

[1] Rafi, M. M.; Rosen, R. T.; Vassil, A. Anticancer Res. 2000, 20, 2653.
[2] Silvia, G.; Andrea, C.; Angela, R.; Federica, B.; Lorna, P.; Anja, P.; Rolf, W. H.; Maurizio, R.; Alessandra, B. J. Med. Chem. 2006, 49, 4777.
[3] Xia, L.; Chi, B. C.; Sung, W. J.; Sompol, P.; Huang, J. J.; Kunyan, H.; Lien, H. P.; Stefan F.; Ge, X.; Jia, Y. H.; Hongbo, R. L.; Ye, K. Q. J. Med. Chem. 2010, 53, 8274.
[4] Yan, X.; Liu, H. Q.; Zou, Y. Q.; Ren, Z. H. Chin. J. Org. Chem. 2008, 28, 1534 (in Chinese).
(延玺, 刘会青, 邹永青, 任占华, 有机化学, 2008, 28, 1534.)
[5] Wang, X. J.; Liu, J. L. Chem. Res. Appl. 2013, 25, 1491 (in Chinese).
(王学军, 刘建利, 化学研究与应用, 2013, 25, 1491.)
[6] Bakerr, W. J. Chem. Soc. 1933, 55, 1381.
[7] Lee, J. I.; Son, H. S.; Park, H. Bull. Korean Chem. Soc. 2004, 25(12), 1945.
[8] Chee, C. F.; Buckle, M. C.; Rahman, N. A. Tetrahedron Lett. 2011, 52, 3120.
[9] Rafi, M. M.; Rosen, R, T.; Vassil, A. Anticancer Res. 2000, 20, 2653.
[10] Zhang, Q. Z.; Yang, X. S.; Hao, X. J. Chin. Tradit. Herb. Drugs 2008, 39, 304 (in Chinese).
(张前军, 杨小生, 郝小江, 中草药, 2008, 39, 304.)
[11] Lechner, D.; Gibbons, S.; Bucar, F. Phytochem. Lett. 2008, 1, 71.
[12] Lee, Y. S.; Kang, O. H.; Choi, J. G. J. Microbiol. 2008, 46, 283.
[13] Chang, P. C.; Li, H. Y.; Tang, H. J. J. Microbiol. Immunol. Infect. 2007, 40, 56.
[14] Stapleton, P. D.; Shah, S.; Anderson, J. C. Int. J. Antimicrob. Agents 2004, 23, 462.
[15] Nong, C. Z.; Ye, H. H.; Wang, L. Chin. J. Hosp. Pharm. 2011, 31, 750 (in Chinese).
(农朝赞, 叶海洪, 王丽, 中国医院药学杂志, 2011, 31, 750.)
[16] Chen, A. H.; Kuo, W. B.; Chen, C. W. J. Chin. Chem. Soc. 2004, 51, 1389.
[17] Tang, L. J.; Zhang, S. F.; Yang, J. Z.; Gao, W. T.; Cui, J. Org. Prep. Proc. Int. 2004, 36, 453.
[18] Jiraporn, U.; Chanpen, W.; Weerasak, S.; Patcharawee, N. J. Mol. Struct. 2011, 1001, 152.
[19] Tara, C. C.; Krishnasami, V. J. Chem. Soc. 1933, 1073.
[20] Bhosale, R. S.; Sarda, S. R.; Giram, R. P. J. Iran. Chem. Soc. 2009, 6, 519.
[21] Liu, X. P.; Wang, Y.; Lan, H. Y. Chem. Res. Chin. Univ. 2010, 26, 268.
[22] Wu, Z.; Jiang, L.; Chen, H. J. Chem. Res. 2009, 3, 195.
[23] Wilson, B. J. Chem. Soc. 1933, 1381.
Options
文章导航

/

〈 〉