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Potential bioactive Vanillin–Schiff base di- and tri-organotin(IV) complexes of 4-((3,5-dimethylphenylimino)methyl)-2-methoxyphenol: synthesis, characterization and biological screenings

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Abstract

Eight different di- and triorganotin(IV) complexes of vanillin-Schiff base of the type R2SnClL and R3SnL [R = Me (1,6), n-Bu (2,7), Ph (3,8), tert-Bu (4), Cy (5) and L = 4-((3,5-dimethylphenylimino)methyl)-2-methoxyphenol] were synthesized. The products were characterized by elemental analysis, FT-IR, 1H, 13C and 119Sn NMR spectroscopy. The ligand 4-((3,5-dimethylphenylimino)methyl)-2-methoxyphenol is also characterized by single crystal X-ray analysis. In the 1H NMR spectra of 1 and 6, the 2 J(119/117Sn-1H) in the Sn-CH3 moiety has 57 and 54 Hz values, respectively, that confirm the formation of four-coordinated Sn species. Moreover, the 13C NMR value for ipso carbon of SnPh is 139 ppm which also confirms the formation of four-coordinated Sn species. The title ligand and its complexes were also screened for their biological activities such as interaction with DNA, enzymatic, antimicrobial, cytotoxic and antioxidant activities. The antimicrobial and cytotoxic activities of triorganotin(IV) derivatives are relatively higher than their corresponding diorganotin(IV) analogues due to their greater lipophilicity and permeability through cell membrane.

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Acknowledgments

M. Sirajuddin (Pin# P7-017) gratefully acknowledges the HEC Islamabad, Pakistan, for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Muhammad Sirajuddin, Saqib Ali, Farooq Ali Shah & Muhammad Ahmad

  2. Department of Physics, University of Sargodha, Sargodha, Pakistan

    Muhammad Nawaz Tahir

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  1. Muhammad Sirajuddin
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Correspondence to Saqib Ali.

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Supplementary material CRystallographic data for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre, CCDC# 814987 for HL. Copies of this information may be obtained free of charge from The Director, CCDC, 12, Union Road, Cambridge CB2 1EZ (FAX +44-1223-336033) or e-mail deposit@ccdc.cam. ac.uk or http://www.ccdc.cam.ac.uk.

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Sirajuddin, M., Ali, S., Shah, F.A. et al. Potential bioactive Vanillin–Schiff base di- and tri-organotin(IV) complexes of 4-((3,5-dimethylphenylimino)methyl)-2-methoxyphenol: synthesis, characterization and biological screenings. J IRAN CHEM SOC 11, 297–313 (2014). https://doi.org/10.1007/s13738-013-0301-x

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