Citation: Fu-Xing ZHANG, Xin DENG, Zhe-Hao YANG, Xin ZHANG, Kang-Xia FU, Liang-Bing SHENG, Xiao-Ming ZHU, Wu-Jiu JIANG, Jiang-Xi YU. Synthesis, structure, and anticancer activity of organotin 9-fluorenone-4-carboxylates[J]. Chinese Journal of Inorganic Chemistry, ;2023, 39(7): 1287-1294. doi: 10.11862/CJIC.2023.092 shu

Synthesis, structure, and anticancer activity of organotin 9-fluorenone-4-carboxylates

  • Corresponding author: Fu-Xing ZHANG, zfx8056@163.com
  • Received Date: 22 November 2022
    Revised Date: 31 March 2023

Figures(8)

  • Three organotin 9-fluorenone-4-carboxylate compounds, triphenyltin 9‑fluorenone‑4‑carboxylate [(C6H5)3Sn(C14H7O3)] (1), tricyclohexyltin 9-fluorenone-4-carboxylate [(C6H11)3Sn(C14H7O3)] (2), and tri(2-methyl-2-phenylpropyl) tin 9-fluorenone-4-carboxylate [(C6H5C(CH3)2CH2)3Sn(C14H7O3)] (3), were synthesized by the solvothermal method using methanol as a solvent. The compounds were characterized by elemental analysis, IR spectroscopy, NMR (1H, 13C, and 119Sn), and thermogravimetric analysis. The crystal structures of the compounds were determined by single-crystal X-ray diffraction. The compounds were studied by quantum chemical calculation and in vitro anticancer activity. The results show that compound 1 has a 1D chain structure and the central tin atom is a five-coordinated distorted trigonal bipyramid configuration; compounds 2 and 3 are single tin nuclear molecules and the tin atoms are four-coordinated distorted tetrahedron configurations. The compounds have good inhibitory activity on the human cervical carcinoma cell line (HeLa), human liver cancer cell line (HUH-7), human non-small cell lung cancer cell line (A549), human lung adenocarcinoma cell line (H1975) and breast cancer cell line (MCF-7).
  • 加载中
    1. [1]

      Sung H, Ferlay J, Siegel R L, Laversanne M, Soerjomataram I, Jemal A, Bray F. Global cancer statistics 2020: GLOBOCAN estimates of incidence and mortality worldwide for 36 cancers in 185 countries[J]. CA Cancer J. Clin., 2021,71:209-249. doi: 10.3322/caac.21660

    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[J]. RSC Adv., 2019,9(6):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[J]. Chem. Rev., 2019,119(2):1058-1137. doi: 10.1021/acs.chemrev.8b00271

    4. [4]

      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[J]. Molecules, 2020,25(4):859-875. doi: 10.3390/molecules25040859

    5. [5]

      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[J]. Appl. Organomet. Chem., 2020,34(1)e5283.

    6. [6]

      Liu J, Lin Y C, Liu M, Wang S Q, Li Y X, Liu X C, Tian L J. Synthesis, structural characterization and cytotoxic activity of triorganotin 5-(salicylideneamino)salicylates[J]. Appl. Organomet. Chem., 2019,33(3)e4715. doi: 10.1002/aoc.4715

    7. [7]

      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[J]. Eur. J. Med. Chem., 2010,45:883-889. doi: 10.1016/j.ejmech.2009.11.026

    8. [8]

      Xiao X, Liang J W, Xie J Y, Liu X, Zhu D S, Dong 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]. J. Mol. Struct., 2017,1146:233-241. doi: 10.1016/j.molstruc.2017.05.141

    9. [9]

      Somesan A A, Vieriu S M, Crăciun A, Silvestru C, Chiroi P, Nutu A, Jurj A, Lajos R, Berindan-Neagoe I, Varga R A. C, O-chelated organotin(Ⅳ) derivatives as potential anticancer agents: Synthesis, characterization, and cytotoxic activity[J]. Appl. Organomet. Chem., 2022,36(3)e6540.

    10. [10]

      Dahmani M, Harit T, Et-touhami A, Yahyi A, Eddike D, Tillard M, Benabbes R. Two novel macrocyclic organotin(Ⅳ) carboxylates based on bipyrazoledicarboxylic acid derivatives: Syntheses, crystal structures and antifungal activities[J]. J. Organomet. Chem., 2021,948121913. doi: 10.1016/j.jorganchem.2021.121913

    11. [11]

      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]. J. Mol. Struct., 2020,1205127635. doi: 10.1016/j.molstruc.2019.127635

    12. [12]

      Ruan B F, Tian Y P, 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[J]. Inorg. Chim. Acta, 2011,365(1):302-308. doi: 10.1016/j.ica.2010.09.024

    13. [13]

      Zhang J H, Zhang R F, Ma C L, Wang D Q, Wang H Z. New organotin carboxylates derived from 6-chloro-3-pyridineacetic acid exhibiting discrete molecular, drum-like, linear polymeric and ladder structures constructed from dimeric tetraorganodistannoxane units[J]. Polyhedron, 2011,30(4):624-631. doi: 10.1016/j.poly.2010.11.035

    14. [14]

      Airapetyan D V, Petrosyan V S, Gruener S V, Zaitsev K V, Arkhipov D E, Korlyukov A A. Disproportionation reactions within the series of coordinated monoorganostannanes[J]. J. Organomet. Chem., 2013,747:241-248. doi: 10.1016/j.jorganchem.2013.07.005

    15. [15]

      Iqbal M, Ali S, Muhammad N, Parvez M, Langer P, Villinger A. Synthesis, characterization, crystal structures and electrochemical studies of organotin(Ⅳ) carboxylates[J]. J. Organomet. Chem., 2013,723:214-223. doi: 10.1016/j.jorganchem.2012.10.006

    16. [16]

      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[J]. Chinese J. Inorg. Chem., 2017,33(5):830-836.  

    17. [17]

      KUANG D Z, YU J X, FENG Y L, ZHU X M, JIANG W J, ZHANG F X. Syntheses, structures and in vitro antitumor activity of bis(tricyclohexyltin) pyridinedicarboxylate with macrocyclic supramolecular structure[J]. Chinese J. Inorg. Chem., 2018,34(6):1035-1042.  

    18. [18]

      ZHANG F X, WANG J Q, KUANG D Z, FENG Y L, ZHANG Z J, XU Z F, ZHANG K. Microwave assisted solid-state synthesis, crystal structure and quantum chemistry of the tri(o-chlorobenzyl)tin cinnamate[J]. Chinese J. Inorg. Chem., 2011,27(6):1111-1115.  

    19. [19]

      Shu S, Zhang F X, Tang R H, Yan S Y, Zhu X M, Sheng L B, Kuang D Z, Feng Y L, Yu J X, Jiang W J. Syntheses, structures and antitumor activities of tri(o-bromobenzyl)tin diethyldithiocarbamate and tri(m-fluorobenzyl)tin pyrrolidine dithiocarbamate[J]. Chin. J. Struct. Chem., 2020,39(3):459-466.

    20. [20]

      LIU X, ZHANG F X, HE L F, LI D W, ZENG W H, JIANG S Y, HE X, SHENG L B, ZHU X M. Synthesis, structure and antitumor activity of two tris(o-bromobenzyl) tin carboxylates[J]. Chinese J. Inorg. Chem., 2022,38(1):46-52.  

    21. [21]

      ZHOU Y L, ZHANG F X, ZHU X M, TIAN J, XU S N, ZHAO B J, CHEN J J, LI F F, DENG X. Synthesis, structure, and anticancer activity of two organotin heterocyclic carboxylates complexes[J]. Chinese J. Inorg. Chem., 2022,38(8):1533-1540.

  • 加载中
    1. [1]

      Jingjing QINGFan HEZhihui LIUShuaipeng HOUYa LIUYifan JIANGMengting TANLifang HEFuxing ZHANGXiaoming 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

    2. [2]

      Haitang WANGYanni LINGXiaqing MAYuxin CHENRui ZHANGKeyi WANGYing ZHANGWenmin WANG . Construction, crystal structures, and biological activities of two Ln3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

    3. [3]

      Xinting XIONGZhiqiang XIONGPanlei XIAOXuliang NIEXiuying SONGXiuguang 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

    4. [4]

      Xin MAYa SUNNa SUNQian KANGJiajia ZHANGRuitao ZHUXiaoli 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

    5. [5]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin 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

    6. [6]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

    7. [7]

      Zhaoyang WANGChun YANGYaoyao SongNa HANXiaomeng LIUQinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114

    8. [8]

      Lu LIUHuijie WANGHaitong WANGYing 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

    9. [9]

      Meirong HANXiaoyang WEISisi FENGYuting 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

    10. [10]

      Jiajun WangGuolin YiShengling GuoJianing WangShujuan LiKe XuWeiyi WangShulai Lei . Computational design of bimetallic TM2@g-C9N4 electrocatalysts for enhanced CO reduction toward C2 products. Chinese Chemical Letters, 2024, 35(7): 109050-. doi: 10.1016/j.cclet.2023.109050

    11. [11]

      Qilu DULi ZHAOPeng NIEBo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006

    12. [12]

      Gaofeng WANGShuwen SUNYanfei ZHAOLixin MENGBohui WEI . Structural diversity and luminescence properties of three zinc coordination polymers based on bis(4-(1H-imidazol-1-yl)phenyl)methanone. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 849-856. doi: 10.11862/CJIC.20230479

    13. [13]

      Peng XUShasha WANGNannan CHENAo WANGDongmei YU . Preparation of three-layer magnetic composite Fe3O4@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 544-554. doi: 10.11862/CJIC.20230239

    14. [14]

      Peng ZHOUXiao CAIQingxiang MAXu LIU . Effects of Cu doping on the structure and optical properties of Au11(dppf)4Cl2 nanocluster. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1254-1260. doi: 10.11862/CJIC.20240047

    15. [15]

      Huan ZHANGJijiang WANGGuang FANLong TANGErlin YUEChao BAIXiao WANGYuqi 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 YANXiaoli CHENMiao CAIJing RENHuali CUIHua YANGJijiang 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]

      Xiaoxia WANGYa'nan GUOFeng SUChun HANLong 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

    18. [18]

      Kaimin WANGXiong GUNa DENGHongmei YUYanqin YEYulu 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

    19. [19]

      Shuyan ZHAO . Field-induced Co single-ion magnet with pentagonal bipyramidal configuration. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1583-1591. doi: 10.11862/CJIC.20240231

    20. [20]

      Bing LIUHuang ZHANGHongliang HANChangwen HUYinglei ZHANG . Visible light degradation of methylene blue from water by triangle Au@TiO2 mesoporous catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 941-952. doi: 10.11862/CJIC.20230398

Metrics
  • PDF Downloads(1)
  • Abstract views(604)
  • HTML views(33)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return