Citation: Wu-Jiu JIANG, Tian-Zi MO, Fu-Xing ZHANG, Dai-Zhi KUANG, Yu-Xing TAN. Syntheses, Crystal Structures and in vitro Anticancer Activities of Dibenzyltin Compounds Based on the N-(2-Phenylacetic acid)-aroyl Hydrazone[J]. Chinese Journal of Structural Chemistry, ;2020, 39(4): 673-681. doi: 10.14102/j.cnki.0254-5861.2011-2522 shu

Syntheses, Crystal Structures and in vitro Anticancer Activities of Dibenzyltin Compounds Based on the N-(2-Phenylacetic acid)-aroyl Hydrazone

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

Corresponding author: Yu-Xing TAN, tanyuxing@hynu.edu.cn
Received Date: 8 July 2019
Accepted Date: 25 November 2019

Fund Project: the Hengyang Normal University College Students Innovation and Entrepreneurship Training Program cxcy1944Scientific Research Fund of Hunan Provincial Education Department 19C0279Hengyang Normal University Industrial Supported Project HXKJ201907Hengyang Normal University Industrial Supported Project HXKJ201908Hengyang Normal University Industrial Supported Project HXKJ201911Hengyang Normal University Industrial Supported Project HXKJ201946Hengyang Normal University Industrial Supported Project HXKJ201947Foundation of Key Laboratory of Functional Organometallic Materials, University of Hunan Province GN19K07

Figures(4)

Two dibenzyltin compounds, {[C₆H₅O(O)C=N–N=C(Ph)COO] (m-Cl–C₆H₄CH₂)₂-Sn(CH₃OH)}₂ (1) and {[p-Me–C₆H₄O(O)C=N–N=C(Ph)COO] (m-Cl–C₆H₄CH₂)₂Sn(CH₃OH)}₂ (2), have been synthesized by microwave "one pot" reaction with benzoylhydrazine (or p-methyl benzhydrazine), phenylglyoxylic acid and di-m-chlorobenzyltin dichloride. Compound 2 contains two crystals 2a and 2b. The compounds have been characterized with IR, elemental analysis, ¹H, ¹³C and ¹¹⁹Sn NMR spectra, H RMS. Three crystals are all binuclear molecules with a Sn₂O₂ four-membered ring plane, and each Sn atom center is seven-coordinated with [SnO₄C₂N] to form a distorted pentagonal bipyramidal configuration. In vitro antitumor activities of all compounds and carboplatin were evaluated by MTT against three human cancer cells such as NCI-H460 (lung cancer cells), HepG2 (liver cancer cells) and MCF7 (breast cancer cells), and compound 2 exhibited better antitumor activity.
- organotin complex,
- hydrazine,
- synthesis,
- crystal structure,
- biological activity
1. [1]
  Rosenberg, B.; Vancamp, L.; Trosko, J. E.; Mansour, V. H. Platinum compounds: a new class of potent antitumour agents. Nature 1969, 222, 385–386. doi: 10.1038/222385a0
2. [2]
  Yan, Y. K.; Melchart, M.; Habtemariam, A.; Sadler, P. J. Organometallic chemistry, biology and medicine: ruthenium arene anticancer complexes. Chem. Commun. 2005, 4764–4776.
3. [3]
  Cao, W.; Qi, J.; Qian, K.; Tian, L.; Cheng, Z.; Wang, Y. Structure-activity relationships of 2-quinolinecarboxaldehyde thiosemicarbazone gallium(Ⅲ) complexes with potent and selective anticancer activity. J. Inorg. Biochem. 2019, 191, 174–182. doi: 10.1016/j.jinorgbio.2018.11.017
4. [4]
  Díaz-García, D.; Cenariu, D.; Pérez, Y.; Cruz, P.; del Hierro, I.; Prashar, S.; Fischer-Fodor, E.; Gómez-Ruiz, S. Modulation of the mechanism of apoptosis in cancer cell lines by treatment with silica-based nanostructured materials functionalized with different metallodrugs. Dalton Trans. 2018, 47, 12284–12299. doi: 10.1039/C8DT01677A
5. [5]
  Attanzio, A.; Ippolito, M.; Girasolo, M. A.; Saiano, F.; Rotondo, A.; Rubino, S.; Mondello, L.; Capobianco, M. L.; Sabatino, P.; Tesoriere, L.; Casella, G. Anti-cancer activity of di- and tri-organotin(Ⅳ) compounds with D-(+)-Galacturonic acid on human tumor cells. J. Inorg. Biochem. 2018, 188, 102–112. doi: 10.1016/j.jinorgbio.2018.04.006
6. [6]
  Shang, X.; Meng, X.; Alegria, E. C. B. A.; Li, Q.; Guedes da Silva, M. F. C.; Kuznetsov, M. L.; Pombeiro, A. J. L. Syntheses, molecular structures, electrochemical behavior, theoretical study, and antitumor activities of organotin(ⅳ) complexes containing 1-(4-chlorophenyl)-1-cyclopentanecarboxylato ligands. Inorg. Chem. 2011, 50, 8158–8167. doi: 10.1021/ic200635g
7. [7]
  Hong, M.; Yang, Y.; Li, C.; Xu, L.; Li, D.; Li, C. Z. Study of the effect of molecular structure and alkyl groups bound with tin(ⅳ) on their cytotoxicity of organotin(ⅳ) 2-phenyl-4-selenazole carboxylates. RSC Adv. 2015, 5, 102885–102894. doi: 10.1039/C5RA18445B
8. [8]
  Basu Baul, T. S.; Dutta, D.; Duthie, A.; Guchhait, N.; Rocha, B. G. M.; Guedes da Silva, M. F. C.; Mokhamatam, R. B.; Raviprakash, N.; Manna, S. K. New dibutyltin(Ⅳ) ladders: syntheses, structures and, optimization and evaluation of cytotoxic potential employing A375 (melanoma) and HCT116 (colon carcinoma) cell lines in vitro. J. Inorg. Biochem. 2017, 166, 34–48. doi: 10.1016/j.jinorgbio.2016.10.008
9. [9]
  Zong, X. J.; Liu, X. R.; Zhao, S. S.; Yang, Z. W. Preparation, thermal analyses and biological activities of Co(Ⅱ) and Cr(Ⅲ) complexes with 2-acetylpyridine-6-bromo-2-naphthoyl acylhydrazone. Polyhedron 2019, 170, 303–311. doi: 10.1016/j.poly.2019.05.059
10. [10]
  Zhou, Y.; Wei, W.; Zhu, L.; Li, Y.; Li, Z. Synthesis and insecticidal activity study of novel anthranilic diamides analogs containing a diacylhydrazine bridge as effective Ca²⁺ modulators. Chem. Biol. Drug Des. 2018, 92, 1914–1919. doi: 10.1111/cbdd.13349
11. [11]
  Wang, H.; Fu, Y.; Fan, Z.; Song, H.; Wu, Q.; Zhang, Y.; Belskaya, N. P.; Bakulev V. A. Synthesis, crystal structure and biological activity of N-tert-butyl-N-(4-methyl-1,2,3-thiadiazole)-5-yl-N-(4-methyl-1,2,3-thiadiazole)-5-formyl- N-3,5-dichloropyridin-2-yl-diacylhydrazine. Chin. J. Struct. Chem. 2011, 30, 412–416.
12. [12]
  Sisido, K.; Takeda, Y.; Kinugawa, Z. Direct synthesis of organotin compounds. I. di- and tribenzyltin chlorides. J. Am. Chem. Soc. 1961, 83, 538–541. doi: 10.1021/ja01464a008
13. [13]
  Sheldrick, G. M. SHELXL-97, A Program for Crystal Structure Refinement. University of Göttingen, Germany 1997.
14. [14]
  Xu, R. R.; Pang, W. Q.; Huo, Q. S. Inorganic Synthesis and Preparative Chemistry. Higher Education Press, Beijing 2009.
15. [15]
  Yin, H. D.; Chen, S. W.; Li, L. W.; Wang, D. Q. Synthesis, characterization and crystal structures of the organotin(Ⅳ) compounds with the Schiff base ligands of pyruvic acid thiophene-2-carboxylic hydrazone and salicylaldehyde thiophene-2-carboxylic hydrazone. Inorg. Chim. Acta 2007, 360, 2215–2223. doi: 10.1016/j.ica.2006.10.038
16. [16]
  Liu, K.; Yan, H.; Chang, G.; Li, Z.; Niu, M.; Hong, M. Organotin(Ⅳ) complexes derived from hydrazone Schiff base: synthesis, crystal structure, in vitro cytotoxicity and DNA/BSA interactions. Inorg. Chim. Acta 2017, 464, 137–146. doi: 10.1016/j.ica.2017.05.017
17. [17]
  Tan, Y.; Zhang, Z.; Tan, Y.; Kuang, D.; Yu, J.; Zhu, X.; Jiang, W. Syntheses, crystal structures and biological activity of the dialkytin complexes based on 2-oxo-3-phenylpropionic acid salicyloylhydrazone. J. Coord. Chem. 2017, 70, 2606–2624. doi: 10.1080/00958972.2017.1355460
18. [18]
  Deacon, G. B.; Phillips, R. J. Relationships between the carbon-oxygen stretching frequencies of carboxylato complexes and the type of carboxylate coordination. Coordin. Chem. Rev. 1980, 33, 227−250. doi: 10.1016/S0010-8545(00)80455-5
19. [19]
  Salam, M. A.; Hussein, M. A.; Ramli, I.; Islam, M. S. Synthesis, structural characterization, and evaluation of biological activity of organotin(Ⅳ) complexes with 2-hydroxy-5-methoxybenzaldehyde-N(4)-methylthiosemicarbazone. J. Organomet. Chem. 2016, 813, 71–77. doi: 10.1016/j.jorganchem.2016.04.007
20. [20]
  Hong, M.; Yin, H.; Zhang, X.; Li, C.; Yue, C.; Cheng, S. Di- and tri-organotin(Ⅳ) complexes with 2-hydroxy-1-naphthaldehyde 5-chloro-2-hydroxybenzoylhydrazone: synthesis, characterization and in vitro antitumor activities. J. Organomet. Chem. 2013, 724, 23–31. doi: 10.1016/j.jorganchem.2012.10.031
21. [21]
  Pretsch, E.; Bühlmann, P.; Badertscher, M. Structure Determination of Organic Compounds, Tables of Spectral Data. Fourth. Springer-Verlag, Berlin Heidelberg 2009.
22. [22]
  Zhang, Z. Z.; Jiang, W. J.; Liu, Y.; Kuang, D. Z.; Yu, J. X.; Zhu, X. M.; Tan, Y. X. Syntheses, crystal structures and biological activity of N-(2-propionic acid)-aroyl hydrazone di-p-methylbenzytin complexes. Chin. J. Inorg. Chem. 2017, 33, 1603–1610.
23. [23]
  Tan, Y. X.; Zhang, Z. Z.; Feng, Y. L.; Yu, J. X.; Zhu, X. M.; Kuang, D. Z.; Jiang, W. J. Syntheses, crystal structures and biological activities of the 2-oxo-butyric acid salicylacylhydrazone dibenzyltin complexes. Chin. J. Struct. Chem. 2017, 36, 925–936.
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