Silicon-containing diorganotin complexes with salicylaldehyde thiosemicarbazone and their anticancer activity

  • Qian Liu
  • Bo Xie
  • Sen LinEmail author
  • Qihua Liao
  • Ruihong Deng
  • Yan ZhaohuaEmail author
Regular Article


Eight novel silicon-containing diorganotin complexes with salicylaldehyde thiosemicarbazone were synthesized. They were characterized by \(^{1}\hbox {H NMR}\), \(^{13}\hbox {C NMR}\), IR spectra, elemental analysis and X-ray single-crystal diffraction. Spectroscopic and X-rays studies indicated that the thiosemicarbazone Schiff base and tin atom were coordinated as a parallel five- and six-membered heterocyclic structure. In addition, the bioassay of the synthesized complexes was performed and the results show that the silicon-containing diorganotin complexes with salicylaldehyde thiosemicarbazone have good anticancer activity on human breast cancer cells.

Graphic Abstract

Eight silicon-containing organotin complexes containing salicylaldehyde thiosemicarbazone derivatives were synthesized. The Sn atom in the complexes were penta-coordinated in a distorted trigonal bipyramidal configuration, forming a five- and six-membered chelate ring through the coordination of oxygen, nitrogen, sulfur atoms. All the complexes showed significant anticancer activity, especially complex 3cb and 3ab.


Diorganotin synthesis structure anticancer activity 


Supplementary material

12039_2019_1650_MOESM1_ESM.pdf (451 kb)
Supplementary material 1 (pdf 451 KB)


  1. 1.
    Yan X T, He B, Liu L H, Qu G B, Shi J B, Liao C Y, Hu L G and Jiang G B 2018 Organotin exposure stimulates steroidogenesis in H295R Cell via cAMP pathway Ecotox. Environ. Saf. 156 148CrossRefGoogle Scholar
  2. 2.
    Ransi D, Neil R E and Tilo S 2015 Organotin carboxylate catalyst in urethane formation in a polar solvent: an experimental and computational study RSC Adv. 5 48935CrossRefGoogle Scholar
  3. 3.
    Muhammad M N and Klaus J 2017 Organotin-based receptors for anions and ion pairs Chem. Commun. 53 8122CrossRefGoogle Scholar
  4. 4.
    Ali A and Adel N 2019 New organotin(IV) chlorides derived from \(N\)-(2-hydroxyphenyl) aryloxy sulfamates, Synthesis, characterization and DSC investigation J. Chem. Sci. 131 12CrossRefGoogle Scholar
  5. 5.
    Jerry O A and Damian C O 2018 Organotin(IV) dithiocarbamate complexes chemistry and biological activity Molecules 23 2571CrossRefGoogle Scholar
  6. 6.
    Tahani I K 2017 Synthesis, characterization, biological and anticancer activity of new Pd(II), Pt(IV), V(III) and Ru(III) complexes with a schiff base ligind deriving from dehydroacetic acid J. Chem. Pharma. Res. 9 164Google Scholar
  7. 7.
    Jai D and Suman D 2017 Synthesis, characterization and antimicrobial evaluation of schiff base complexes derived from [2,2’-(ethylenedioxy)bis(ethylamine)] and 5-chlorosalicylaldehyde Der. Pharma. Chem. 9 89Google Scholar
  8. 8.
    Jose M G, Teresa R A, Antonio N C, Simon H O and Elizabeth G 2017 Schiff base Sn(IV) complexes as cytotoxic agents: synthesis, structure, isosteric and bioisosreric replacement J. Organomet. Chem. 848 332CrossRefGoogle Scholar
  9. 9.
    Miljan N M, Aliona D, Ghenadie N, Nevenka G, Sinisa R, Jozef K, Peter R, Eva A E and Vladimir B A 2017 Effects of terminal substitution and iron coordination on antiproliferative activity of L-proline-salicylaldehyde-thiosemicarbazone hybrids Eur. J. Inorg. Chem. 40 4773Google Scholar
  10. 10.
    Nisha G, Anitta R T, Radhu S and Mary N L 2017 Plasmon-enhanced, two-photon absorption in Schiff-base-modified poly(styrene-co-maleic anhydride)-gold nanocomposites J. Appl. Polym. Sci. 134 46Google Scholar
  11. 11.
    Wasinee P, Victor M, Casey G D, Guy N L, Boujemaa M and Keith S M 2016 Ligand effects in a heteroleptic bis-tridentate iron(III) spin crossover complex showing a very high \(\text{ T }_{1/2}\) value Chem. Commun. 52 1443CrossRefGoogle Scholar
  12. 12.
    Haque R A and Salam M A 2015 Synthesis, structural characterization and biological activities of organotin(IV) complexes with 5-allyl-2-hydroxy-3-methoxybenzaldehyde-4- thiosemicarbazone J. Chem. Sci. 127 1589CrossRefGoogle Scholar
  13. 13.
    Shikha I, Tarlok S L, Henna S, Daljit S A, Geeta H and Jerry P J 2016 Synthesis, spectroscopy, structures and antimicrobial activity of mixed-ligind zinc(II) complexes of 5-nitro-salicylaldehyde thiosemicarbazones New J. Chem. 40 3642CrossRefGoogle Scholar
  14. 14.
    Pahontu E, Fala V, Gulea A, Poirier D, Tapcov V and Rosu T 2013 Synthesis and characterization of some new Cu(II), Ni(II) and Zn(II) complexes with salicylidene thiosemicarbazones: antibacterial antifungal and in vitro antileukemia activity Molecules 18 8812CrossRefGoogle Scholar
  15. 15.
    Niu L, Li Y L and Li Q S 2014 Medicinal properties of organotin compounds and their limitations caused by toxicity Inorg. Chim. Acta 423 2CrossRefGoogle Scholar
  16. 16.
    Matichenkov V V, Bocharnikova E A, Pahnenko E P, Khomiakov D M, Matichenkov I V, Zhan Q and Wei X 2016 Reduction of Cd, Cu, Ni, and Pb mobility by active Si in a laboratory study Mine Water Environ. 35 302CrossRefGoogle Scholar
  17. 17.
    Xie Q L, Sha G L and Liu Y L 1994 The Synthesis of [(phenyldimehtylsilyl) methyl] dicyelohexylitn dihtio-phosphates Chin. J. Org. Chem. 14 536Google Scholar
  18. 18.
    Kalaivani P, Prabhakaran R, Kaveri M V, Huang R, Staples R J and Natarajan K 2013 Synthesis, spectral, X-ray crystallography, electrochemistry, DNA/protein binding and radical scavenging activity of new palladium(II) complex containing triphenylarsine Inorg. Chim. Acta 405 415CrossRefGoogle Scholar
  19. 19.
    Lin S, Guo Y Y, Deng R H and Huang Z Q 2013 Catalytic activities of dialkytin compounds containing silicon to the condensation reaction of acetal(ketal)-alcohol Chin. J. Appl. Chem. 30 271Google Scholar
  20. 20.
    Mala N and Pramendra K S 2011 Chemistry and applications of organotin(IV) complexes of schiff bases Dalton Trans. 40 7077CrossRefGoogle Scholar
  21. 21.
    Lin S, Fu Z F, He X L, Liu H Y, Sun X Q, Wang X and Lu L D 2006 Synthesis, structure and anticancer activity of cyclohexyl (trimethysilylmethylene) tin diaromatase Chin. J. Org. Chem. 26 856Google Scholar
  22. 22.
    Gong G F, Song R, Zou Y B and Lin S 2013 Synthesis, characterization and antitumour activity of diorganotin (IV) complexes containing cilicon of 2-mercaptobenzothiazole Chin. J. Org. Chem. 33 803CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  1. 1.Department of ChemistryNanchang UniversityNanchangPeople’s Republic of China

Personalised recommendations