Abstract
Seven new diorganotin(IV) complexes, [Me2SnL] (1), [Et2SnL] (2), [(n-Bu2SnL] (3), [Ph2SnL] (4), [(n-Oct2SnL] (5), [tert-Bu2SnL] (6), and [n-BuClSnL] (7) have been synthesized from the reaction of N′-(2-hydroybenzylidene)-4-tert-butylbenzohydrazide (H2L) with the corresponding diorganotin(IV) dichloride/oxide or organotin(IV) chloride dihydroxide. The synthesized compounds were structurally characterized by FT-IR, multinuclear NMR (1H and 13C) spectroscopies, elemental analysis, mass spectrometry, DFT/(B3LYP) calculations, and, for ligand single crystal, X-ray diffraction analysis. Spectroscopic evidence affirms coordination of ligand to the dialkyltin(IV) moieties through oxygen nitrogen donor sites in iminol form. The 1 J(119Sn, 13C) coupling constants, 584-655 Hz and 2 J(119Sn-1H) coupling constant, 79 Hz for complex (1), suggest pentacoordination around Sn atom in solution. Single-crystal X-ray structure of ligand show its existence in amido form. Supramolecular architecture mediated by N(2)-H···O(2) and C-H…π interactions is formed in solid state. The DFT calculations have been performed to obtain various structure-based molecular properties as well as to support experimental results. The synthesized compounds were screened in vitro against various human pathogenic microbial strains. Escherichia coli and Staphylococcus aureus were most visibly inhibited by complexes (4) and (7). Highest antifungal activity was shown by compound (6) against Fusarium solani. Compound (3) displayed highest cytotoxicity among synthesized compounds with LD50 0.44μg/mL.
Graphical Abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Anwer J, Ali S, Shahzadi S, Shahid M, Sharma SK, Qanungo K (2013) Synthesis, characterization, semi-empirical study and biological activities of homobimetallic complexes of tranexamic acid with organotin(IV). J Coord Chem 66:1142–1152. https://doi.org/10.1080/00958972.2013.776678
Armarego WL, Chai CLL (2013) Purification of laboratory chemicals. Butterworth-Heinemann, USA
Atta-ur-Rahman CM, Thomsen WJ (2001) Bioassay techniques for drug development. Harwood Academic Publishers, The Netherlands
Ayers PW, Anderson JS, Bartolotti LJ (2005) Perturbative perspectives on the chemical reaction prediction problem. Int J Quantum Chem 101:520–534. https://doi.org/10.1002/qua.20307
Ayoko GA, Bonire JJ, Abdulkadir SS, Olurinola PF, Ehinmidu JO, Kokot S, Yiasel S (2003) A multicriteria ranking of organotin(IV) compounds with fungicidal properties. Appl Organomet Chem 17:749–758. https://doi.org/10.1002/aoc.520
Becke AD (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys Rev A 38:3098. https://doi.org/10.1103/PhysRevA.38.3098
Beurskens P, Beurskens G, De Gelder R, Garcia-Granda S, Gould R, Israel R, Smits J (1999) The DIRDIF-99 program system. Crystallography Laboratory, University of Nijmegen, Nijmegen
Borba A, Albrecht M, Gómez-Zavaglia A, Suhm MA, Fausto R (2010) Low temperature infrared spectroscopy study of pyrazinamide: from the isolated monomer to the stable low temperature crystalline phase. J Phys Chem A 114:151–161. https://doi.org/10.1021/jp907466h
Bruker S (2006) SAINTPLUS and XPREP. Area Detector Control and Integration Software. Smart Apex Software Reference Manuals. Bruker Analytical X-ray Instruments Inc, Madison
Chaudhary P, Swami M, Sharma D, Singh R (2009) Ecofriendly synthesis, antimicrobial and antispermatogenic activity of triorganotin (IV) complexes with 4′-nitrobenzanilide semicarbazone and 4′-nitrobezanilide thiosemicarbazone. Appl Organomet Chem 23:140–149. https://doi.org/10.1002/aoc.1484
Chermette H (1999) Chemical reactivity indexes in density functional theory. J Comput Chem 20:129–154. https://doi.org/10.1002/(SICI)1096-987X(19990115)20:1<129:AID-JCC13>3.0.CO;2-A
Dennington R, Keith T, Millam JG (2009) GaussView, Ver. 5.0.9 Semichem Inc, Shawnee Mission KS USA
Fani S, Kamalidehghan B, Lo KM, Hashim NM, Chow KM, Ahmadipour F (2015) Synthesis, structural characterization, and anticancer activity of a monobenzyltin compound against MCF-7 breast cancer cells. Drug Des Devel Ther 9:6191–6201. https://doi.org/10.2147/DDDT.S87064
Finney D (1971) Probit analysis, 3rd edn. Cambridge University Press, London
Frisch M et al. (2009) Gaussian 09, revision D. 01. Gaussian, Inc., Wallingford CT
Fukushima K, Dubey SK, Suzuki S (2012) YgiW homologous gene from Pseudomonas aeruginosa 25 W is responsible for tributyltin resistance. J Gen Appl Microbiol 58:283–289. https://doi.org/10.2323/jgam.58.283
Geerlings P, De Proft F (2008) Conceptual DFT: the chemical relevance of higher response functions. PCCP 10:3028–3042. https://doi.org/10.1039/B717671F
Geerlings P, De Proft F, Langenaeker W (2003) Conceptual density functional theory. Chem Rev 103:1793–1874. https://doi.org/10.1021/cr990029p
Gholivand K, EbrahimiValmoozi AA, Gholami A, Dusek M, Eigner V, Abolghasemi S (2016) Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates. J Organomet Chem 806:33–44. https://doi.org/10.1016/j.jorganchem.2015.09.030
Girasolo MA, Attanzio A, Sabatino P, Tesoriere L, Rubino S, Stocco G (2014) Organotin(IV) derivatives with 5,7-disubstituted-1,2,4-triazolo[1,5-a]pyrimidine and their cytotoxic activities: the importance of being conformers. Inorg Chim Acta 423(Part B):168–176. https://doi.org/10.1016/j.ica.2014.07.015
Holeček J, Lyčka A (1986) Dependence of| 1J (119Sn13C)| on the C- Sn- C angle in n-butyltin (IV) compounds. Inorg Chim Acta 118:L15–L16
Hong M, Yin H-D, Cui J-C (2011) Weakly-bridged dimeric diorganotin (IV) compounds derived from pyruvic acid hydrazone Schiff base ligands: synthesis, characterization and crystal structures. Solid State Sci 13:501–507. https://doi.org/10.1016/j.solidstatesciences.2010.11.010
Kohn W, Becke AD, Parr RG (1996) Density functional theory of electronic structure. J Phys Chem 100:12974–12980. https://doi.org/10.1021/jp960669l
Kovala-Demertzi D, Dokorou V, Primikiri A, Vargas R, Silvestru C, Russo U, Demertzis MA (2009) Organotin meclofenamic complexes: synthesis, crystal structures and antiproliferative activity of the first complexes of meclofenamic acid—Novel anti-tuberculosis agents. J Inorg Biochem 103:738–744. https://doi.org/10.1016/j.jinorgbio.2009.01.014
Lee C, Yang W, Parr R (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density. Phys Rev B: Condens Matter 37(2):785–789
Lockhart TP, Manders WF (1986) Structure determination by NMR spectroscopy. Dependence of| 2J (119Sn, 1H)| on the Me-Sn-Me angle in methyltin(IV) compounds. Inorg Chem 25:892–895. https://doi.org/10.1021/ic00227a002
Meetsma A (2001) PLUTO. Molecular graphics program. University of Groningen, The Netherlands
Muhammad N, Zia-Ur-Rehman Shujah S, Shah A, Ali S, Meetsma A, Hussain Z (2012) Syntheses, structural characteristics, and antimicrobial activities of new organotin (IV) 3-(4-bromophenyl)-2-ethylacrylates. J Coord Chem 65:3766–3775. https://doi.org/10.1080/00958972.2012.718076
Parr R, Yang W (1989) Density functional theory of atoms and molecules. Oxford Univ Press, New York
Parr RG, Yang W (1995) Density-functional theory of the electronic structure of molecules. Annu Rev Phys Chem 46:701–728. https://doi.org/10.1146/annurev.pc.46.100195.003413
Pettinari C, Marchetti F, Pettinari R, Martini D, Drozdov A, Troyanov S (2001) Synthesis and characterisation of tin (IV) and organotin (IV) derivatives 2-{[(2-hydroxyphenyl) imino] methyl} phenol. Inorg Chim Acta 325:103–114. https://doi.org/10.1016/S0020-1693(01)00654-5
Rehman W, Baloch MK, Badshah A (2008) Synthesis, spectral characterization and bio-analysis of some organotin (IV) complexes. Eur J Med Chem 43:2380–2385. https://doi.org/10.1016/j.ejmech.2008.01.019
Roy M, Roy S, Singh KS, Kalita J, Singh SS (2016) Synthesis, characterisation and anti-diabetic activities of triorganotin (IV) azo-carboxylates derived from amino benzoic acids and resorcinol: crystal structure and topological study of a 48 membered macrocyclic-tetrameric trimethyltin(IV) complex. Inorg Chim Acta 439:164–172. https://doi.org/10.1016/j.ica.2015.10.012
Sharma S, Meena R, Singh RV, Fahmi N (2016) Synthesis, characterization, antimicrobial, and DNA cleavage evaluation of some organotin(IV) complexes derived from ligands containing the 1H-indole-2,3-dione moiety. Main Group Met Chem 39:31–40. https://doi.org/10.1515/mgmc-2015-0030
Sheldrick G (1997) SHELX-97: Programs for crystal structure analysis Göttingen, Germany
Shpakovsky D et al (2014) Synthesis, antiradical activity and in vitro cytotoxicity of novel organotin complexes based on 2, 6-di-tert-butyl-4-mercaptophenol. Dalton Trans 43:6880–6890. https://doi.org/10.1039/C3DT53469C
Shujah S, Muhammad N, Ali S, Khalid N, Tahir MN (2011) New dimeric and supramolecular organotin (IV) complexes with a tridentate schiff base as potential biocidal agents. J Organomet Chem 696:2772–2781. https://doi.org/10.1016/j.jorganchem.2011.04.010
Shujah S, Muhammad N, Shah A, Ali S, Khalid N, Meetsma A (2013) Bioactive hepta-and penta-coordinated supramolecular diorganotin (IV) Schiff bases. J Organomet Chem 741:59–66. https://doi.org/10.1016/j.jorganchem.2013.05.019
Sirajuddin M, Ali S, McKee V, Zaib S, Iqbal J (2014) Organotin(iv) carboxylate derivatives as a new addition to anticancer and antileishmanial agents: design, physicochemical characterization and interaction with Salmon sperm DNA. RSC Adv 4:57505–57521. https://doi.org/10.1039/C4RA10487K
Spek A (1998) PLATON. Program for the Automated Analysis of Molecular Geometry
Tariq M, Ali S, Muhammad N, Shah NA, Sirajuddin M, Tahir MN, Khalid N, Khan MR (2014) Biological screening, DNA interaction studies, and catalytic activity of organotin (IV) 2-(4-ethylbenzylidene) butanoic acid derivatives: synthesis, spectroscopic characterization, and X-ray structure. J Coord Chem 67:323–340. https://doi.org/10.1080/00958972.2014.884217
Zhang Y-Y, Zhang R-F, Zhang S-L, Cheng S, Li Q-L, Ma C-L (2016) Syntheses, structures and anti-tumor activity of four new organotin(iv) carboxylates based on 2-thienylselenoacetic acid. Dalton Trans 45:8412–8421. https://doi.org/10.1039/C6DT00532B
Zia ur R, Muhammad N, Shuja S, Ali S, Butler IS, Meetsma A, Khan M (2009) New dimeric, trimeric and supramolecular organotin(IV) dithiocarboxylates: synthesis, structural characterization and biocidal activities. Polyhedron 28:3439–3448. https://doi.org/10.1016/j.poly.2009.07.025
Acknowledgements
The authors are thankful to Higher Education Commission of Pakistan for the financial support.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
11696_2017_333_MOESM1_ESM.docx
Supplementary material: CCDC reference number 993525 contains the supplementary crystallographic data for N′-(2-hydroxybenzylidene)-4-tert-butylbenzohydrazide (H2L). These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.ac.uk/data_request/cif. Electronic Supplementary Material associated with this article can be found in the online version of this paper (DOI: xxxxxxxxxx) (DOCX 7686 kb)
Rights and permissions
About this article
Cite this article
Shujah, S., Ali, S., Khalid, N. et al. Synthesis, spectroscopic characterization, X-ray structure, DFT calculations, and antimicrobial studies of diorganotin (IV) complexes of monotopic oxygen nitrogen donor Schiff base. Chem. Pap. 72, 903–919 (2018). https://doi.org/10.1007/s11696-017-0333-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11696-017-0333-2