Citation: LIU Jiao, LI Zhuo-Qun, YI Yu-Yang, ZHONG Yi-Xin, YU Hao-Tian, TAN Yu-Xing, JIANG Wu-Jiu. Syntheses, Crystal Structures and in Vitro Anticancer Activity of Four Binuclear Benzyltin Complexes Based on Acylhydrazone Ligand[J]. Chinese Journal of Inorganic Chemistry, ;2019, 35(12): 2200-2208. doi: 10.11862/CJIC.2019.269 shu

Syntheses, Crystal Structures and in Vitro Anticancer Activity of Four Binuclear Benzyltin Complexes Based on Acylhydrazone Ligand

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

Corresponding author: JIANG Wu-Jiu, jwj_china@163.com
Received Date: 27 June 2019
Revised Date: 7 October 2019

Figures(3)

Four dinuclear benzyltin complexes were synthesized by microwave "one-pot synthesis", namely {[C₄H₃S(O)C=N-N=C(Me)COO](PhCH₂)₂Sn(MeOH)}₂ (C1), {[C₄H₃S(O)C=N-N=C(Me)COO](p-Cl-C₆H₄CH₂)₂Sn(MeOH)}₂ (C2), {[C₄H₃S(O)C=N-N=C(PhCH2)COO](PhCH₂)₂Sn(MeOH)}₂ (C3), {[C₄H₃S(O)C=N-N=C(PhCH₂)COO](p-Cl-C₆H₄CH₂)₂Sn(MeOH)}₂ (C4). The complexes C1~C4 were characterized by IR, ¹H NMR, ¹³C NMR¹¹⁹Sn NMR spectra, elemental analysis, HRMS and the crystal structures were determined by X-ray diffraction. The four complexes are all binuclear molecules, and there was a Sn₂O₂ four-membered ring in the middle of the molecule. The central tin atom and the coordinating atom form a seven-coordinated pentagonal bipyramid configuration. The thermogravimetric of the complexes C1~C4 were analyzed, and in vitro antitumor activities of the complexes were evaluated by MTT against three human cancer cell lines (H460, HepG2, MCF7). The results show that complex C2 is the best compound for inhibiting cancer cells in the four synthesized complexes.
- organotin complex,
- acylhydrazone,
- synthesis,
- crystal structure,
- activity
1. [1]
  Rosenberg B, Vancamp L, Trosko J E, et al. Nature, 1969, 222(5191):385-386 doi: 10.1038/222385a0
2. [2]
  Kenny R G, Marmion C J. Chem. Rev., 2019, 119(2):1058-1137 doi: 10.1021/acs.chemrev.8b00271
3. [3]
  Díaz-García D, Cenariu D, Pérez Y, et al. Dalton Trans., 2018, 47(35):12284-12299 doi: 10.1039/C8DT01677A
4. [4]
  Cao W B, Qi J X, Qian K, et al. J. Inorg. Biochem., 2019, 191:174-182 doi: 10.1016/j.jinorgbio.2018.11.017
5. [5]
  Hong M, Geng H L, Niu M J, et al. Eur. J. Med. Chem., 2014, 86:550-561 doi: 10.1016/j.ejmech.2014.08.070
6. [6]
  Wang H, Hu L, Du W, et al. ACS Biomater. Sci. Eng., 2017, 3(5):836-842 doi: 10.1021/acsbiomaterials.6b00786
7. [7]
  Hong M, Yang Y, Li C, et al. RSC Adv., 2015, 5(124):102885-102894 doi: 10.1039/C5RA18445B
8. [8]
  Baul T S B, Dutta D, Duthie A, et al. J. Inorg. Biochem., 2017, 166:34-48 doi: 10.1016/j.jinorgbio.2016.10.008
9. [9]
  Benítez J, de Queiroz A C, Correia I, et al. Eur. J. Med. Chem., 2013, 62:20-27 doi: 10.1016/j.ejmech.2012.12.036
10. [10]
  Li X Q, Gan Y Y, Meng J, et al. J. Heterocycl. Chem., 2018, 55(6):1382-1390 doi: 10.1002/jhet.3172
11. [11]
  WANG Wan-Wan, WANG Yuan, ZHANG Ling, et al. Chinese J. Inorg. Chem., 2019, 35(3):563-568
12. [12]
  Sisido K, Takeda Y, Kinugawa Z, et al. J. Am. Chem. Soc., 1961, 83(3):538-541 doi: 10.1021/ja01464a008
13. [13]
  Sheldrick G M. SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
14. [14]
  XU Ru-Ren, PANG Wen-Qin, HUO Qi-Sheng. Inorganic Synthesis and Preparative Chem-istry. Beijing: Higher Education Press, 2009.
15. [15]
  Yin H D, Chen S W, Li L W, et al. Inorg. Chim. Acta, 2007, 360(7):2215-2223 doi: 10.1016/j.ica.2006.10.038
16. [16]
  Liu K, Yan H, Chang G L, et al. Inorg. Chim. Acta, 2017, 464:137-146 doi: 10.1016/j.ica.2017.05.017
17. [17]
  Hong M, Yin H D, Zhang X Y, et al. J. Organomet. Chem., 2013, 724:23-31 doi: 10.1016/j.jorganchem.2012.10.031
18. [18]
  Deacon G B, Phillips R J. Coord. Chem. Rev., 1980, 33(3):227-250 doi: 10.1016/S0010-8545(00)80455-5
19. [19]
  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
20. [20]
  Tan Y X, Zhang Z J, Tan Y H, et al. J. Coord. Chem., 2017, 70(15):2606-2624 doi: 10.1080/00958972.2017.1355460
21. [21]
  Pretsch E, Buhlmann P, Martin B. Structure Determination of Organic Compounds: Tables of Spectral Data. 4th Ed. Berlin, Heidelberg: Springer-Verlag Berlin Heidelberg, 2009.
22. [22]
  Hong M, Chang G, Li R, et al. New J. Chem., 2016, 40(9):7889-7900 doi: 10.1039/C6NJ00525J
23. [23]
  ZHANG Zhi-Jian, JIANG Wu-Jiu, LIU Yang, et al. Chinese J. Inorg. Chem., 2017, 33(9):1603-1610
24. [24]
  Tan Y X, Zhang Z J, Feng Y L, et al. Chin. J. Struct. Chem., 2017, 36(6):925-936
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沈阳化工大学材料科学与工程学院沈阳 110142