Citation: ZHANG Zhi-Jian, JIANG Wu-Jiu, LIU Yang, KUANG Dai-Zhi, YU Jiang-Xi, ZHU Xiao-Ming, TAN Yu-Xing. Syntheses, Crystal Structures and Biological Activity of N-(2-Propionic acid)-aroyl Hydrazone Di-p-methylbenzytin Complexes[J]. Chinese Journal of Inorganic Chemistry, ;2017, 33(9): 1603-1610. doi: 10.11862/CJIC.2017.198 shu

Syntheses, Crystal Structures and Biological Activity of N-(2-Propionic acid)-aroyl Hydrazone Di-p-methylbenzytin Complexes

Key Laboratory of Functional Organometallic Materials of Hengyang Normal University, College of Hunan Province, College of Chemistry and Material Science, Hengyang Normal University, Hengyang, Hunan 421008, China

Corresponding author: TAN Yu-Xing, 358050086@qq.com
Received Date: 4 May 2017
Revised Date: 1 August 2017

Figures(8)

Two substituted benzyltin complexes (C1, C2) has been synthesized via the reaction of N-(2-propionic acid)-aroyl hydrazone with di-p-methylbenzytin dichloride. The complexes C1 and C2 have been characterized by IR, UV-Vis, ¹H NMR, ¹³C NMR ¹¹⁹Sn NMR spectra, elemental analysis and the crystal structures have been determined by X-ray diffraction. In vitro antitumor activities of both complexes were evaluated by the 3-(4, 5-dimethylthiazoly-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay against three human cancer cell lines(H460, HepG2, MCF7) and a human cell line(HL7702). Two complexes exhibit strong antitumor activity, moreover, C2 is less toxic than C1. The result of EB fluorescent probe shows the interaction between complexes and calf thymus DNA is intercalation. CCDC: 1457502, C1; 1547503, C2.
- organotin complex,
- hydrazone,
- synthesis,
- crystal structure,
- biological activity
1. [1]
  Albert J, Bosque R, Crespo M, et al. Dalton Trans., 2015, 44(30):13602-13614 doi: 10.1039/C5DT01713K
2. [2]
  Fang S, Chen L, Yu M, et al. Org. Biomol. Chem., 2015, 13(16):4714-4726 doi: 10.1039/C5OB00007F
3. [3]
  Zou B Q, Lu X, Qin Q P, et al. RSC Adv., 2017, 7(29):17923-17933 doi: 10.1039/C7RA00826K
4. [4]
  Yan B R, Lü X Y, Du H, et al. Chem. Pap.-Chem. Zvesti, 2016, 70(7):983-993
5. [5]
  Crowe A J, Smith P J. Atassi Ghanem. Chem.-Biol. Interact., 1980, 32(1/2):171-178
6. [6]
  Xuan H, Zhang J, Wang Y, et al. Bioorg. Med. Chem. Lett., 2016, 26(2):570-574 doi: 10.1016/j.bmcl.2015.11.072
7. [7]
  Salam M A, Hussein M A, Ramli I, et al. J. Organomet. Chem., 2016, 813:71-77 doi: 10.1016/j.jorganchem.2016.04.007
8. [8]
  Tabassum S, Yadav S, Arjmand F. Inorg. Chim. Acta, 2014, 423B:38-45
9. [9]
  Sirajuddin M, Ali S, McKee V, et al. RSC Adv., 2014, 4(101):57505-57521 doi: 10.1039/C4RA10487K
10. [10]
  Roy M, Roy S, Singh K S, et al. New J. Chem., 2016, 40(2):1471-1484 doi: 10.1039/C5NJ02637G
11. [11]
  Ferreira I P, Piló E D L, Recio-Despaigne A A, et al. Bioorg. Med. Chem., 2016, 24(13):2988-2998 doi: 10.1016/j.bmc.2016.05.007
12. [12]
  Mohanraj M, Ayyannan G, Raja G, et al. J. Photochem. Photobiol. B, 2016, 158:164-173 doi: 10.1016/j.jphotobiol.2016.03.005
13. [13]
  Sedaghat T, Ebrahimi Y, Carlucci L, et al. J. Organomet. Chem., 2015, 794:223-230 doi: 10.1016/j.jorganchem.2015.06.034
14. [14]
  HAN Jie, ZHOU Xiao-Xia, CHEN Si-Bao, et al. Chin. J. Org. Chem., 2014, 34(4):741-748
15. [15]
  REN Zheng, KANG Yu-Hua, SHI Zhen-Yu, et al. Acta Pharm. Sin., 2010, 45(9):1109-1115
16. [16]
  Foscolos A S, Papanastasiou I, Foscolos G B, et al. Med. Chem. Commun., 2016, 7(6):1229-1236 doi: 10.1039/C6MD00035E
17. [17]
  HE Shui-Yang, CAO Wen-Kai, CHEN Jun-Li, et al. Chem. J. Chinese Universities, 2002, 23(6):991-995
18. [18]
  Sisido K, Takeda Y, Kinugawa Z, et al. J. Am. Chem. Soc., 1961, 83(3):538-541 doi: 10.1021/ja01464a008
19. [19]
  Armarego W L F, Chai C L L. Purification of Laboratory Chemicals. 6th Ed. Oxford:Butterworth-Heinemann, 2009.
20. [20]
  Sheldrick G M. SHELXTL Version 5.03, Siemens Analytical X-ray Division, Madison, Wisconsin, USA, 1994.
21. [21]
  Deacon G B, Phillips R J. Coord. Chem. Rev., 1980, 33:227-250 doi: 10.1016/S0010-8545(00)80455-5
22. [22]
  Jiang W J, Yang N F, Kuang D Z, et al. Chin. J. Struct. Chem., 2011, 30(9):1327-1331
23. [23]
  Yang Y, Hong M, Xu L, et al. J. Organomet. Chem., 2016, 804:48-58 doi: 10.1016/j.jorganchem.2015.12.041
24. [24]
  Pretsch E, Buhlmann P, Martin B. Structure Determination of Organic Compounds:Tables of Spectral Data. 4th Ed. Berlin and Heidelberg:Springer-Verlag, 2009.
25. [25]
  Hong M, Yin H, Chen S, et al. J. Organomet. Chem., 2010, 695(5):653-662 doi: 10.1016/j.jorganchem.2009.11.035
26. [26]
  Baba H S, Dietz C, Lutter M, et al. Organometallics, 2015, 34(23):5555-5565 doi: 10.1021/acs.organomet.5b00768
27. [27]
  Wagner M, Zobel B, Dietz C, et al. Organometallics, 2015, 34(23):5602-5608 doi: 10.1021/acs.organomet.5b00829
28. [28]
  Jímenez-Pérez V M, Camacho-Camacho C, Güizado-Rodríuez M, et al. J. Organomet. Chem., 2000, 614-615:283-293 doi: 10.1016/S0022-328X(00)00689-6
29. [29]
  Hong M, Yin H, Chen S, et al. J. Organomet. Chem., 2010, 695(5):653-662 doi: 10.1016/j.jorganchem.2009.11.035
30. [30]
31. [31]
  Effenberger K, Breyer S, Schobert R. Eur. J. Med. Chem., 2010, 45(5):1947-1954 doi: 10.1016/j.ejmech.2010.01.037
32. [32]
  Dandawate P, Khan E, Padhye S, et al. Bioorg. Med. Chem. Lett., 2012, 22(9):3104-3108 doi: 10.1016/j.bmcl.2012.03.060
33. [33]
  ZHAO Guo-Liang, SHI Xia, ZHANG Jun-Ping, et al. Sci. China:Chem., 2010, 40(10):1525-1535
34. [34]
35. [35]
  SHAO Ying, TONG Jing-Jing, WU Zhu-Hong, et al. J. Changzhou Univ.:Nat. Sci. Ed., 2016, 28(6):38-43
36. [36]
  ZHENG Jian-Hua, LIU Jun, XIAO Yao, et al. Chin. J. Appl. Chem., 2015, 32(5):562-569 doi: 10.11944/j.issn.1000-0518.2015.05.140324
37. [37]
  ZHAO Guo-Liang, SHEN Jin-Bei, SHI Xia, et al. Chinese J. Inorg. Chem., 2012, 28(5):959-964
38. [38]
  Yin H, Liu H, Hong M, et al. J. Organomet. Chem., 2012, 713(15):11-19
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