Citation: Liu Juan, Zhang Yaling, Zhang Xiquan, Gu Hongmei, Li Baolin. Synthesis and Antitumor Activity of New Lapatinib Derivatives[J]. Chemistry, ;2016, 79(4): 360-365. shu

Synthesis and Antitumor Activity of New Lapatinib Derivatives

1.
1. Key Laboratory of Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an 710062;
2.
2. Chia Tai Tianqing Pharmaceutical Co. Ltd., Nanjing 210038

Corresponding author: Li Baolin,
Received Date: 10 September 2015
Available Online: 16 November 2015
Fund Project:

Four new lapatinib derivatives were prepared using N'-(2-cyano-4-iodophenyl)-N,N-dimethyl-formamidine as the starting material by Dimroth rearrangement, Suzuki coupling, reductive amination in turn. The structures of the reaction intermediates and target compounds were characterized with the NMR, IR and HRMS. The antitumor activities of these compounds on SW480, A549 and A431 tumor cells were tested preliminarily by the MTT method in vitro experiment. The results indicated that they had significant inhibition on the growth of tumor cells, especially compound 5a showed good growth inhibitory activity on all the test cells (IC₅₀:5.78~13.38μmol/L) which is similar as that of lapatinib (IC₅₀:4.80~14.90μmol/L).
- Lapatinib,
- Anti-tumor activity,
- Synthetic
1. [1]
  [1] 常卫华, 王留兴, 樊锐太. 肿瘤基础与临床, 2009, 22(3):270~271.
2. [2]
  [2] 余宗艳, 齐宇红, 梁军. 现代肿瘤医学, 2014, 22(3):697~701.
3. [3]
  [3] D W Rusnak, K Lackey, K Affleck et al. Mol. Cancer Ther., 2001, 1(2):85~94.
4. [4]
  [4] E Giannopoulou, A Antonacopoulou, K Floratou et al. Cancer Chemother. Pharmacol., 2009, 63(6):973~981.
5. [5]
  [5] D M Havaleshko, S C Smith, H Cho et al. Neoplasia, 2009, 11(11):1185~1193.
6. [6]
  [6] K J Kimball, T M Numnum, T O Kirby et al. Gynecol. Oncol., 2008, 111(1):95~101.
7. [7]
  [7] 冯焕荣, 李青, 王海琳. 现代生物医学进展, 2012, 12(4):746~747.
8. [8]
  [8] 贾玉才, 卢俊金, 李宝林等. 陕西师范大学学报, 2013, 41(6):42~45.
9. [9]
  [9] 王帆, 刘小莉, 李宝林等. 中国药物化学杂志, 2011, 21(2):151~154.
10. [10]
  [10] 高宏亮, 王留昌, 李宝林等. 化学通报, 2014, 77(10):974~979.
11. [11]
  [11] J P Gilday, M J Welham. WO 2005023783, 2005.
12. [12]
  [12] 孙键, 任宇飞, 高勇等. 化学通报, 2013, 76(5):451~454.
13. [13]
  [13] V Chandregowda, G V Rao, G C Reddy. Org. Proc. Res. Dev., 2007, 11(5):813~816.
14. [14]
  [14] 张庆文, 周后元, 尤启冬. 中国药科大学学报, 2010, 41(4):317~320.
15. [15]
  [15] 季兴, 王武伟, 李飞等. 中国医药工业杂志, 2009, 40(11):801~804.
16. [16]
  [16] 张齐华, 容元伟, 李宝林等. 化学研究与应用, 2014, 26(7):1095~1098.
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沈阳化工大学材料科学与工程学院沈阳 110142