Citation: Xu-Liang TAN, Fu-Xing ZHANG, Li-Fang HE, Shi-Yin GUI, Yi-Ling ZHANG, Xiao-Ming ZHU, Liang-Bing SHENG, Yong-Lan FENG, Jiang-Xi YU, Wu-Jiu JIANG. Syntheses, Structures and Anticancer Activities of Two Tri(o-halobenzyl)tin Substituted Benzoates[J]. Chinese Journal of Structural Chemistry, ;2021, 40(5): 675-681. doi: 10.14102/j.cnki.0254–5861.2011–3080 shu

Syntheses, Structures and Anticancer Activities of Two Tri(o-halobenzyl)tin Substituted Benzoates

Department of Chemistry and Materials 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, Hunan 421008, China

Corresponding author: Fu-Xing ZHANG, zfx8056@163.com
Received Date: 25 December 2020
Accepted Date: 16 March 2021

Fund Project: the open fund project of Hunan Provincial innovation platform 18K089the key project of Hunan Provincial education department 19A070the open fund of Hunan Provincial key laboratory M018K07

Figures(5)

Tri(o-chlorobenzyl)tin 2, 4, 6-trimethylbenzoate (1) and tri(o-bromobenzyl)tin salicylate (2) were synthesized and characterized by elemental analysis, IR spectroscopy, NMR (¹H, ¹³C and ¹¹⁹Sn), thermogravimetric analysis, and single-crystal X-ray diffraction. The initio calculation and in vitro anticancer activity test were performed for compounds 1 and 2. They are both single tin nucleus structures and the tin atoms were tetracoordinated in a distorted tetrahedral configuration; Compounds 1 and 2 showed stronger anticancer activity than cisplatin in human cervical cancer cells (Hela), liver cancer cells (HuH-7), non-small cell lung cancer cells (A549), lung adenocarcinoma cells (H1975) and breast cancer (MCF-7).
- tri(o-chlorobenzyl)tin 2,
- 4,
- 6-trimethylbenzoate,
- tri(o-bromobenzyl)tin salicylate,
- crystal structure,
- quantum chemistry,
- in vitro antitumor activity
1. [1]
  Zhang, R. S.; Sun, K. X.; Zhang, S. W.; Zeng, H. M.; Zou, X. N.; Chen, R.; Gu, X. Y.; Wei, W. Q.; He, J. Report of cancer epidemiology in china 2015. Chin. J. Ondol. 2019, 40, 19–28.
2. [2]
  Zaki, M.; Hairat, S.; Aazam, E. S. Scope of organometallic compounds based on transition metal-arene systems as anticancer agents: starting from the classical paradigm to targeting multiple strategies. RSC Adv. 2019, 9, 3239–3278. doi: 10.1039/C8RA07926A
3. [3]
  Kenny, R. G.; Marmion, C. J. Toward multi-targeted platinum and ruthenium drugs - a new paradigm in cancer drug treatment regimens. Chem. Rev. 2019, 119, 1058–1137. doi: 10.1021/acs.chemrev.8b00271
4. [4]
  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
5. [5]
  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
6. [6]
  Yusof, E. N. M.; Latif, M. A. M.; Tahir, M. I. M.; Sakoff, J. A.; Veerakumarasivam, A.; Page, A. J.; Tiekink, E. R. T.; Ravoof, T. B. S. A. Homoleptic tin(IV) compounds containing tridentate ONS dithiocarbazate Schiff bases: synthesis, X-ray crystallography, DFT and cytotoxicity studies. J. Mol. Struct. 2020, 1205, 127635–127643. doi: 10.1016/j.molstruc.2019.127635
7. [7]
  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.
8. [8]
  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, 38, 270–276.
9. [9]
  Attanzio, A.; D'Agostino, S.; Busà, R.; Frazzitta, A.; Rubino, S.; Girasolo, M. A.; Sabatino, P.; Tesoriere, L. Cytotoxic activity of organotin(IV) derivatives with triazolopyrimidine containing exocyclic oxygen atoms. Molecules 2020, 25, 859–875. doi: 10.3390/molecules25040859
10. [10]
  Kumari, R.; Banerjee, S.; Roy, P.; Nath, M. Organotin(IV) complexes of NSAID, ibuprofen, X-ray structure of Ph₃Sn(IBF), binding and cleavage interaction with DNA and in vitro cytotoxic studies of several organotin complexes of drugs. Appl. Organometal. Chem. 2019, 34, e5283–e5306.
11. [11]
  Liu, J.; Lin, Y.; Liu, M.; Wang, S.; Li, Y.; Liu, X.; Tian, L. Synthesis, structural characterization and cytotoxic activity of triorganotin 5-(salicylideneamino)salicylates. Appl. Organometal. Chem. 2019, 33, e4715–e4724. doi: 10.1002/aoc.4715
12. [12]
  Shu, S.; Zhang, F. X.; Tang, R. H.; Yan, S. Y.; Zhu, X. M.; Sheng, L. B.; Kuang, D. Z.; Yu, J. X.; Jiang, W. J. Syntheses, structures and antitumor activities of tri(o-bromobenzyl)tin diethyldithiocarbamate and tri(m-fluorobenzyl)tin pyrrolidine dithiocarbamate. Chin. J. Struct. Chem. 2020, 39, 459–466.
13. [13]
  Jiang, W. J.; Kuang, D. Z.; Yu, J. X.; Feng, Y. L.; Zhang, F. X.; Wang, J. Q. Synthesis, crystal structure, quantum chemistry and thermal stability of the bis-oxygen-bridged tetranuclear dibutyltin (2, 4, 6-trimethyl)benzoate. Chin. J. Inorg. Chem. 2020, 28, 2363–2368.
14. [14]
  Feng, Y. L.; Kuang, D. Z.; Zhang, F. X.; Yu, J. X.; Jiang, W. J.; Zhu, X. M. Two di-n-butyltin carboxylates with a Sn₄O₄ ladder-like framework: microwave solvothermal syntheses, structures and in vitro antitumor activities. Chin. J. Inorg. Chem. 2017, 33, 830–836.
15. [15]
  Feng, Y. L.; Kuang, D. Z.; Zhang, F. X.; Yu, J. X.; Jiang, W. J.; Zhu, X. M. Microwave-solvothermal syntheses, crystal structures and in vitro antitumor activities of two bis[oxo-bis(aromatic carboxylato dibutyltin)]. Chin. J. Inorg. Chem. 2017, 33, 589–594.
16. [16]
  Liu, C. L.; Xu, D.; Wen. Q.; Wang, H. X.; Xie, M. S.; Zhu, D. S. Synthesis, characterizations and thermal stability of a tricyclohexyltin carboxylate based on substituted isophthalic acid. Chem. Bull. 2014, 77, 819–822.
17. [17]
  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.
18. [18]
  Zhang, F. X.; He, T. F.; Yao, S. F.; Zhu, X. M.; Sheng, L. B.; Kuang, D. Z.; Yu, J. X.; Jiang, W. J. Synthesis, crystal structures and in vitro antitumor activity of two organotin hydroxybenzoate. Chin. J. Inorg. Chem. 2019, 35, 598–604.
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Jingjing QING , Fan HE , Zhihui LIU , Shuaipeng HOU , Ya LIU , Yifan JIANG , Mengting TAN , Lifang HE , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
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]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  Sikai Wu , Xuefei Wang , Huogen Yu . Hydroxyl-enriched hydrous tin dioxide-coated BiVO4 with boosted photocatalytic H2O2 production. Chinese Journal of Structural Chemistry, 2024, 43(12): 100457-100457. doi: 10.1016/j.cjsc.2024.100457
19. [19]
  Shiyi WANG , Chaolong CHEN , Xiangjian KONG , Lansun ZHENG , Lasheng LONG . Polynuclear lanthanide compound [Ce₄^ⅢCe₆^Ⅳ(μ₃-O)₄(μ₄-O)₄(acac)₁₄(CH₃O)₆]·2CH₃OH for the hydroboration of amides to amine. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 88-96. doi: 10.11862/CJIC.20240342
20. [20]
  Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(314)
HTML views(8)

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