Note

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).

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.

Cite this article

Liu Haibin , Xu Huijuan , L? Ping , Pan Ningning , Li Shuangqi . Synthesis and in vitro Antitumor Activities of 6,7-Dimethoxy-4-piperazinquinazoline Thiosemicarbazone Derivatives[J]. Acta Chimica Sinica, 2012 , 0(05) : 674 -678 . DOI: 10.6023/A1108171

References

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.
Outlines

/