SIOC English
化学学报
高级检索

化学学报 >

2012 , Vol. 0 >Issue 05: 674 - 678

DOI: https://doi.org/10.6023/A1108171

研究简报

6,7-二甲氧基-4-哌嗪喹唑啉缩氨基硫脲衍生物的合成及体外抗肿瘤活性研究

  • 刘海彬 ,
  • 徐惠娟 ,
  • 吕萍 ,
  • 潘宁宁 ,
  • 李双奇
展开
  • 辽宁科技学院生物医药与化学工程学院 本溪 117004

收稿日期: 2011-08-17

  修回日期: 2011-11-28

  网络出版日期: 2011-11-29

基金资助

辽宁省教育厅科研项目(No. L2010204)、辽宁省高等学校优秀人才支持计划(No. LJQ2011130)、辽宁科技学院博士启动金(No. 0906B1)资助项目.

收起

Synthesis and in vitro Antitumor Activities of 6,7-Dimethoxy-4-piperazinquinazoline Thiosemicarbazone Derivatives

  • Liu Haibin ,
  • Xu Huijuan ,
  • L? Ping ,
  • Pan Ningning ,
  • Li Shuangqi
Expand
  • School of Biomedical & Chemical Engineering, Liaoning Institute of Science and Technology, Benxi 117004

Received date: 2011-08-17

  Revised date: 2011-11-28

  Online published: 2011-11-29

Supported by

Project was supported by the Program of Liaoning Provincial Committee of Education (No. L2010204), the Program for Liaoning Excellent Talents in University (No. LJQ2011130) and the Ph. D. Program Foundation of Liaoning Institute of Science and Technology (No. 0906B1).

Fold

摘要

以4,5-二甲氧基-2-氨基苯甲酸和醋酸甲眯为起始原料, 经环化、氯化、取代和缩合四步反应, 设计、合成了六个未见文献报道的含有缩氨基硫脲的喹唑啉衍生物4a～4f, 其结构用1H NMR, 13C NMR, ESI-MS, IR 及元素分析测试技术进行了表征. 采用MTT 法测试了化合物4a～4f 对人胃癌SGC-7901、人口腔表皮样癌KB 和人纤维肉瘤HT-1080的体外抗肿瘤活性. 初步的测试结果表明, 化合物4a 和4f 对HT1080 表现出显著的抗肿瘤活性.

关键词： 喹唑啉; 缩氨基硫脲; 抗肿瘤活性; MTT 法

本文引用格式

刘海彬 , 徐惠娟 , 吕萍 , 潘宁宁 , 李双奇 . 6,7-二甲氧基-4-哌嗪喹唑啉缩氨基硫脲衍生物的合成及体外抗肿瘤活性研究[J]. 化学学报, 2012 , 0(05) : 674 -678 . DOI: 10.6023/A1108171

Abstract

Six new quinazoline derivatives 4a～4f bearing thiosemicabazone have been designed and synthesized by four step reactions of cyclization, chlorination, substitution and condensation using 2-amino-4,5-dimethoxybenzoic acid and methanimidamide acetate as starting materials. Their structures were confirmed by 1H NMR, 13C NMR, ESI-MS, IR techniques and elemental analysis. The in vitro antitumor activities of compounds 4a～4f against SGC-7901 (human gastric cancer), KB (human oral epidermoid cancer) and HT-1080 (human fibrosarcoma) cell lines were tested using colorimetric MTT assay. The preliminary results indicated that compounds 4a and 4f showed significant antitumor activity against HT1080.

Key words： quinazoline; thiosemicarbazone; antitumor activity; MTT assay

参考文献

1 Lim, J. K.; Negash, K.; Hanraham, S. M.; VanBrocklin, H. F. J. Labelled Compd. Radiopharm. 2000, 43, 1183.  

2 Nakamura, H.; Onagi, S. Tetrahedron Lett. 2006, 47, 2539.  

3 Fang, H.; Li, M. Y.; Xia, L. Chin. Chem. Lett. 2007, 18, 41.  

4 Lokker, N. A.; Sullivan, C. M.; Hollenbach, S. J.; Israel, M. A.; Giese, N. A. Cancer Res. 2002, 62, 3729.

5 Nakamura, K.; Yamamoto, A.; Kamishohara, M.; Takahashi, K.; Tagushi, K.; Taguchi, E.; Miura, T.; Kubo, K.; Shibuya, M.; Isoe, T. Mol. Cancer Therapeutics 2004, 3, 1639.

6 Ding, M.-W.; Yang, S.-J.; Chen, Y.-F. Chin. J. Org. Chem.2004, 24, 923 (in Chinese). (丁明武, 杨尚君, 陈云峰, 有机化学, 2004, 24, 923.)

7 Yang, S.; Liu G.; Song, B.-A.; Jin, L.-H.; Hu, D.-Y.; Zhang, S.-M. Chin. J. Org. Chem. 2006, 26, 1429 (in Chinese). (杨松, 刘刚, 宋宝安, 金林红, 胡德禹, 张素梅, 有机化 学, 2006, 26, 1429.)

8 Yong, J.-P.; HaJi, A.-A. Chin. J. Org. Chem. 2008, 28, 1204 (in Chinese). (雍建平, 阿吉艾克拜尔·艾萨, 有机化学, 2008, 28,1204.)

9 Li, M.-X.; Zhang, D.; Zhang, L.-Z.; Niu, J.-Y.; Ji, B.-S. J. Org. Chem. 2011, 696, 852.  

10 Duan, L.-P.; Zhang, H.-B. Arabian J. Chem. 2011, 4, 231.

11 Bharti, N.; Maury, M. R.; Naqvi, F.; Azam, A. Bioorg. Med. Chem. Lett. 2000, 10, 2243.  

12 Fujii, N.; Mallari, J. P.; Hansell, E. J.; Mackey, Z.; Doyle, P.; Zhou, Y. M.; Gut, J.; Rosenthal, P. J.; McKerrow, J. H.; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 121.  

13 Easmon, J.; Pürstinger G.; Heinisch G.; Roht, T.; Fiebig H. H.; Holzer, W.; Juger, W.; Jenny, M.; Hofmann, J. J. Med. Chem. 2001, 449, 2164.

14 Li, Q. H. J. Southwest Univ. Nat. (Nat. Sci. Ed.) 2009, 35, 309 (in Chinese). (李清寒, 西南民族大学学报(自然科学版), 2009, 35,309.)

15 Hu, W.-X.; Sun, N.; Yang, Z.-Y. Chin. J. Med. Chem. 2001,11, 129 (in Chinese). (胡惟孝, 孙楠, 杨忠愚, 中国药物化学杂志, 2001, 11,129.)

16 Aly, M. M.; Mohamed, Y. A.; El-Bayouki, K. A. M.; Basyouni, W. M.; Abbas, S. Y. Eur. J. Med. Chem. 2010,45, 3365.
Options
文章导航

/

〈 〉