Citation: Shan SHU, Fu-Xing ZHANG, Rui-Hai TANG, Shi-Yu YAN, Xiao-Ming ZHU, Liang-Bing SHENG, Dai-Zhi KUANG, Yong-Lan FENG, Jiang-Xi YU, Wu-Jiu JIANG. Syntheses, Structures and Antitumor Activities of Tri(o-bromobenzyl)tin Diethyldithiocarbamate and Tri(m-fluorobenzyl)tin Pyrrolidine Dithiocarbamate[J]. Chinese Journal of Structural Chemistry, ;2020, 39(3): 459-466. doi: 10.14102/j.cnki.0254–5861.2011–2465 shu

Syntheses, Structures and Antitumor Activities of Tri(o-bromobenzyl)tin Diethyldithiocarbamate and Tri(m-fluorobenzyl)tin Pyrrolidine Dithiocarbamate

Department of Chemistry and Material Science, Hengyang Normal University; Key Laboratory of Functional Metal-organic Complexes of Hunan Province; Key Laboratory of Functional Organometallic Materials of Colleges of Hunan Province, Hengyang, Human 421008, china

Corresponding author: Fu-Xing ZHANG, zfx8056@163.com
Received Date: 19 May 2019
Accepted Date: 2 September 2019

Fund Project: the Open Fund Project of Innovation Platform Hunan Province Higher Educational Institutions 18K089

Figures(5)

Tri(o-bromobenzyl)tin diethyldithiocarbamate (1) and tri(m-fluorobenzyl)tin pyrrolidine dithiocarbamate (2) have been synthesized and characterized by elemental analysis, IR spectroscopy, NMR (¹H, ¹³C and ¹¹⁹Sn), thermogravimetric analysis and single-crystal X-ray diffraction. The two complexes crystallize in the triclinic system space group P\begin{document}$ \overline 1 $\end{document}. For complex 1, a = 0.9770(1), b = 1.1011(1), c = 1.4583(1) nm, α = 78.431(1)°, β = 86.307(1)°, γ = 69.712(1)°, V = 1.4417(2) nm³, Z = 2, D_c = 1.790 g/cm³, μ(MoKα) = 52.04 cm^–1, F(000) = 756, R = 0.0434 and wR = 0.0593. For complex 2, a = 0.7055(1), b = 1.3349(3), c = 1.3782(3) nm, α = 89.216(2)°, β = 82.044(2)°, γ = 84.637(2)°, V = 1.2799(5) nm³, Z = 2, D_c = 1.537 g/cm³, μ(MoKα) = 11.98 cm^–1, F(000) = 596, R = 0.0313 and wR = 0.0333. The two complexes represent mononuclear structures with five-coordinated [SnC₃S₂] cores forming a distorted trigonal bipyramid. The quantum chemical calculations of 1 and 2 have been investigated. The antitumor activity shows that 1 and 2 have higher activities than cisplatinum against Colo205, HepG2, MCF-7, Hela and H460 cell line in vitro.
1. [1]
  Vieira, F. T.; Lima, G. M.; Maia, J. R. S.; Speziali, N. L.; Ardisson, J. D.; Rodrigues, L.; Junior, A. C.; Romero, O. B. Synthesis, characterization and biocidal activity of new organotin complexes of 2-(3-oxocyclohex-1-enyl)benzoic acid. Eur. J. Medi. Chem. 2010, 45, 883–889. doi: 10.1016/j.ejmech.2009.11.026
2. [2]
  Xiao, X.; Liang, J. G.; Xie, J. Y. Organotin(Ⅳ) carboxylates based on 2-(1, 3-dioxo-1H-benzo(de)-isoquinolin-2(3H)-yl)acetic acid: syntheses, crystal structures, luminescent properties and antitumor activities. J. Mol. Struct. 2017, 1146, 233–241. doi: 10.1016/j.molstruc.2017.05.141
3. [3]
  Munoz-Flores, B. M.; Santillán, R.; Farfán, N. Synthesis, X-ray diffraction analysis and nonlinear optical properties of hexacoordinated organotin complexes derived from Schiff bases. J. Organomet. Chem. 2014, 769, 64–71. doi: 10.1016/j.jorganchem.2014.07.002
4. [4]
  Yang, G.; Hong, M.; Xu, L. D. Organotin(Ⅳ) complexes derived from Schiff base N΄-((1E)-(2-hydroxy-3-methoxyphenyl) methylidene)pyridine-3-carbohydrazone: synthesis, in vitro cytotoxicities and DNA/BSA interaction. J. Organomet. Chem. 2016, 804, 48–58. doi: 10.1016/j.jorganchem.2015.12.041
5. [5]
  He, T. F.; Zhang, F. X.; Yao, S. F.; Zhu, X. M.; Sheng, L. B.; Kuang, D. Z.; Feng, Y. L.; Yu, J. X.; Jiang. W. J. Synthesis, crystal structure and biological activities of a novel anionic organotin(Ⅳ) complex {((p-ClC₆H₄CH₂)Sn(H₂O)(Cl)₂OCOCH(O)CH(O)CO₂Sn(H₂O)(Cl)₂(p-ClC₆H₄CH₂))·2(HNEt₃)}. Chin. J. Struct. Chem. 2019, 37, 1899–1906.
6. [6]
  Zhang, F. X.; Tao, J.; Kuang, D. Z.; Yu, J. X.; Jiang, W. J.; Zhu, X. M. Synthesis, crystal structure and properties of triphenyltin complex with salicylidene-2-aminophenol. Chin. J. Struct. Chem. 2019, 37, 270–276.
7. [7]
  Ruan, B. F.; Tian, Y. U.; Zhou, H. P.; Wu, J. Y.; Hu, R. T.; Zhu, C. H.; Yang, J. X.; Zhu, H. L. Synthesis, characterization and in vitro antitumor activity of three organotin(Ⅳ) complexes with carbazole ligand. Inorg. Chim. Acta 2011, 365, 302–308. doi: 10.1016/j.ica.2010.09.024
8. [8]
  Yan, W. H.; Kang, W. L.; Li, J. H. Synthesis, crystal structure and antibacterial activity of ain-butyltin di-2-(2-formylphenoxy)acetic ester. Chin. J. Appl. Chem. 2007, 24, 660–664.
9. [9]
  Shujha, S.; Shah, A.; Rehman, Z. U.; Muhammad, N.; Ali, S.; Qureshi, R.; Khalid, N.; Meetsma, A. Diorganotin(Ⅳ) derivatives of ONO tridentate Schiff base: synthesis, crystal structure, in vitro antimicrobial, anti-leishmanial and DNA binding studies. Eur. J. Med. Chem. 2010, 45, 2902–2911. doi: 10.1016/j.ejmech.2010.03.015
10. [10]
  Zhang, F. X.; Kuang, D. Z.; Wang, J. Q.; Feng, Y. L.; Xu, Z. F.; Chen, Z. M.; Zeng, R. Y. Synthesis, crystal structure and quantum chemistry of the ring-form dimer tris(o-methylbenzyl)tin hydroxide. Chin. J. Org. Chem. 2008, 28, 1457–1461.
11. [11]
  Yin, H. D.; Wang, Y.; Wang, C. H. Synthesis and crystal structure of di(p-chlorbenzyl)tin bis(dithiomorpholin carbamate) and chlorodi(p-chlorbenzyl)tin dithioethylcarbamat. Chin. J. Struct. Chem. 2004, 23, 926–931.
12. [12]
  Yin, H. D.; Wang, C. H.; Ma, C. L. Synthesis and crystal structure of tri(p-fluorobenzyl)tin chloride and tri(p-fluorobenzyl)tin N, N-(1, 4-butylene)dithiocarbamate. Chin. J. Org. Chem. 2004, 24, 34–39.
13. [13]
  Kuma, A.; Singh, A.; Yadav, R.; Singh, S.; Kociok-Köhn, G.; Trivedi, M. Supramolecular architecture of organotin(Ⅳ) N-methyl ferrocenyl N-ethanol dithiocarbamates: crystallographic and computational studies. J. Inorg. Chim. Acta 2018, 471, 234–243. doi: 10.1016/j.ica.2017.11.016
14. [14]
  Zhang, F. X.; Kuang, D. Z.; Feng, Y. L.; Wang, J. Q.; Yu, J. X.; Jiang, W. J.; Zhu, X. M. Synthesis, structure and antitumor activity of dis(o-bromobenzyl)tin bis(dithiomethylcarbamate) and dis(o-chlorobenzyl)tin bis(pyrrolidine dithiocarbamate). Chin. J. Inorg. Chem. 2014, 34, 2367–2374.
15. [15]
  Zhang, F. X.; Kuang, D. Z.; Feng, Y. L.; Wang, J. Q.; Yu, J. X.; Jiang, W. J.; Zhu, X. M. Synthesis, structure and antitumor activity of tri(o-bromobenzyl)tin dithiotetrahydropyrrolocarbamate. Chin. J. Appl. Chem. 2014, 31, 285–289.
16. [16]
  Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure. University of Göttingen, Germany 1977.
17. [17]
  Yin, H. D.; Wang, Y.; Zhang, R. F.; Ma, C. L. Synthesis and characterization of triphenylgermaniumdithiocarbamates. Chem. J. Chin. Univer. 2000, 21, 1231–1233.
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