Citation: Mo Tianzi, Yu Haotian, Tan Yuxing, Liu Mengqin, Zhang Fuxing, Kuang Daizhi, Jiang Wujiu. Syntheses, Crystal Structures and Biological Activities of Arylformylhydrazone Di-p-methylbenzyltin Complexes[J]. Chemistry, ;2019, 82(11): 1001-1007, 994. shu

Syntheses, Crystal Structures and Biological Activities of Arylformylhydrazone Di-p-methylbenzyltin Complexes

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 421008

Corresponding author: Jiang Wujiu, jwj_china@163.com
Received Date: 21 April 2019
Accepted Date: 3 August 2019

Figures(8)

Two p-methylbenzyl tin complexes containing Sn₂O₂ four-membered ring {[R(O)C=N-N=C(CH₂Ph)COO] (p-Me-C₆H₄CH₂)₂Sn(CH₃OH)}₂ (R=p-NO₂-C₆H₄-or C₄H₃S-) (C1、C2) have been synthesized via the reaction of the 2-oxo-3-phenylpropionic p-nitrobenzoyl arylformylhydrazone and 2-oxo-3-phenylpropionic-2-thiophene arylformylhydrazone with di-p-methylbenzyl tin dichloride, respectively. The complexes C1 and C2 have been characterized by IR, ¹H NMR, ¹³C NMR, ¹¹⁹Sn NMR spectra, HRMS, elemental analysis and X-ray diffraction. The in vitro inhibitory activities of C1 and C2 on cancer cells NCI-H460, HepG2 and MCF7 were tested. The results showed that C1 and C2 have good inhibitory effects on three kinds of cancer cells, and C1 is slightly better than C2. The interaction between C1 and calf thymus DNA was tested by UV, fluorescence and viscosity methods, the results indicated that the interaction of the complex to DNA is intercalation. Gel electrophoresis studies showed that complex C1 can effectively cleave DNA pBR322.
- Organotin complex,
- Hydrazone,
- Synthesis,
- Crystal structure,
- Biological activity
1. [1]
  B Rosenberg, L Vancamp, J E Trosko et al. Nature, 1969, 222 (5191): 385~386.
2. [2]
  T Karasawa, P S Steyger. Toxicol Lett., 2015, 237 (3): 219~227.
3. [3]
  N Milosavljevic, C Duranton, N Djerbi et al. Cancer Res., 2010, 70 (19): 7514~7522.
4. [4]
  M Zaki, S Hairat, E S Aazam RSC Adv., 2019, 9 (6): 3239~3278.
5. [5]
  W Cao, J Qi, K Qian et al. J. Inorg. Biochem., 2019, 191: 174~182.
6. [6]
  R G Kenny, C J Marmion. Chem. Rev., 2019, 119 (2): 1058~1137.
7. [7]
  A J Crowe, P J Smith, G Atassi. Chem-biol Interact., 1980, 32 (1): 171~178.
8. [8]
9. [9]
  A Jana, S Konar, T N Mandal et al. Polyhedron, 2012, 46 (1): 105~112.
10. [10]
11. [11]
  L Qu, H Xu, X Wang et al. ACS Omega, 2017, 2 (9): 5974~5980.
12. [12]
  T Xu, X Wang, Q Zhang et al. Bioorg. Med. Chem. Lett., 2018, 28 (20): 3376~3380.
13. [13]
  K Sisido, Y Takeda, K Dinugawa. J. Am. Chem. Soc., 1961, 83, 538~541.
14. [14]
  G M Sheldrick, SHELXL-97, A Program for Crystal Structure Refinement., University of Geöttingen, Germany, 1997.
15. [15]
  A M Pyle, J P Rehmann, R Meshoyrer et al. J. Am. Chem. Soc., 1989, 111 (8): 3051~3058.
16. [16]
  C Tan, J Liu, L Chen et al. J. Inorg. Biochem., 2008, 102 (8): 1644~1653.
17. [17]
  M Hong, H Yin, X Zhang et al. J. Organomet. Chem., 2013, 724: 23~31.
18. [18]
  M A Salam, M A Hussein, I Ramli et al. J. Organomet. Chem., 2016, 813: 71-77.
19. [19]
  G B Deacon, R J Phillips. Coordin. Chem. Rev., 1980, 33(3): 227-250.
20. [20]
  E Pretsch, P Bühlmann, M Badertscher, Structure Determination of Organic Compounds, Springer-Verlag Berlin Heidelberg, 2009.
21. [21]
22. [22]
23. [23]
  K Liu, H Yan, G Chang et al. Inorg. Chim. Acta, 2017, 464: 137-146.
24. [24]
  G Yao, M Ye, R Huang et al. Bioorg. Med. Chem. Lett., 2014, 24(2): 501-507.
25. [25]
  C Yan, J Zhang, T Liang et al. Biomed. Pharmacother., 2015, 71: 119-127.
26. [26]
  N Ganji, A Rambabu, N Vamsikrishna et al. J. Mol. Struct., 2018, 1173: 173-182.
27. [27]
  Y Zhao, Z Li, H Li et al. Inorg. Chim. Acta, 2018, 482: 136-143.
28. [28]
  I M El-Deen, A F Shoair, M A El-Bindary. J. Mol. Liq., 2018, 249: 533-545.
29. [29]
  Z Mirzaei-Kalar. J. Pharm. Biomed., 2018, 161: 101-109.
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