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.
1. [1]
  Yao HUANG , Yingshu WU , Zhichun BAO , Yue HUANG , Shangfeng TANG , Ruixue LIU , Yancheng LIU , Hong LIANG . Copper complexes of anthrahydrazone bearing pyridyl side chain: Synthesis, crystal structure, anticancer activity, and DNA binding. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 213-224. doi: 10.11862/CJIC.20240359
2. [2]
  Lulu DONG , Jie LIU , Hua YANG , Yupei FU , Hongli LIU , Xiaoli CHEN , Huali CUI , Lin LIU , Jijiang WANG . Synthesis, crystal structure, and fluorescence properties of Cd-based complex with pcu topology. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 809-820. doi: 10.11862/CJIC.20240171
3. [3]
  Xiaoling WANG , Hongwu ZHANG , Daofu LIU . Synthesis, structure, and magnetic property of a cobalt(Ⅱ) complex based on pyridyl-substituted imino nitroxide radical. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 407-412. doi: 10.11862/CJIC.20240214
4. [4]
  Jia JI , Zhaoyang GUO , Wenni LEI , Jiawei ZHENG , Haorong QIN , Jiahong YAN , Yinling HOU , Xiaoyan XIN , Wenmin WANG . Two dinuclear Gd(Ⅲ)-based complexes constructed by a multidentate diacylhydrazone ligand: Crystal structure, magnetocaloric effect, and biological activity. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 761-772. doi: 10.11862/CJIC.20240344
5. [5]
  Lu LIU , Huijie WANG , Haitong WANG , Ying LI . Crystal structure of a two-dimensional Cd(Ⅱ) complex and its fluorescence recognition of p-nitrophenol, tetracycline, 2, 6-dichloro-4-nitroaniline. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1180-1188. doi: 10.11862/CJIC.20230489
6. [6]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
7. [7]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478
8. [8]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
9. [9]
  Ruikui YAN , Xiaoli CHEN , Miao CAI , Jing REN , Huali CUI , Hua YANG , Jijiang WANG . Design, synthesis, and fluorescence sensing performance of highly sensitive and multi-response lanthanide metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 834-848. doi: 10.11862/CJIC.20230301
10. [10]
  Yinling HOU , Jia JI , Hong YU , Xiaoyun BIAN , Xiaofen GUAN , Jing QIU , Shuyi REN , Ming FANG . A rhombic Dy₄-based complex showing remarkable single-molecule magnet behavior. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 605-612. doi: 10.11862/CJIC.20240251
11. [11]
  Xiumei LI , Yanju HUANG , Bo LIU , Yaru PAN . Syntheses, crystal structures, and quantum chemistry calculation of two Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 2031-2039. doi: 10.11862/CJIC.20240109
12. [12]
  Xiumei LI , Linlin LI , Bo LIU , Yaru PAN . Syntheses, crystal structures, and characterizations of two cadmium(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 613-623. doi: 10.11862/CJIC.20240273
13. [13]
  Yan XU , Suzhi LI , Yan LI , Lushun FENG , Wentao SUN , Xinxing LI . Structure variation of cadmium naphthalene-diphosphonates with the changing rigidity of N-donor auxiliary ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 395-406. doi: 10.11862/CJIC.20240226
14. [14]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
15. [15]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
16. [16]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
17. [17]
  Huan ZHANG , Jijiang WANG , Guang FAN , Long TANG , Erlin YUE , Chao BAI , Xiao WANG , Yuqi ZHANG . A highly stable cadmium(Ⅱ) metal-organic framework for detecting tetracycline and p-nitrophenol. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 646-654. doi: 10.11862/CJIC.20230291
18. [18]
  Meirong HAN , Xiaoyang WEI , Sisi FENG , Yuting BAI . A zinc-based metal-organic framework for fluorescence detection of trace Cu²⁺. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1603-1614. doi: 10.11862/CJIC.20240150
19. [19]
  Shuyan ZHAO . Field-induced Co^Ⅱ single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231
20. [20]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(447)
HTML views(7)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142