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Synthesis, structural elucidation and biological activities of organotin(IV) derivatives of 4-(2-thienyl)butyric acid

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Abstract

A series of tri- and diorganotin(IV) derivatives of 4-(2-thienyl)butyric acid have been synthesized by the reaction of ligand acid with tri- and diorganotin salts in 1:1 and 2:1 molar ratios, respectively. The synthesized compounds have been confirmed by CHNS elemental analyses, FTIR, multinuclear NMR (1H and 13C) spectroscopy and X-ray diffraction studies. NMR data reveal a 5-coordinate geometry for the triorganotin(IV) derivatives, while 6-coordinate for the diorganotin(IV) derivatives, respectively. The X-ray crystallographic analysis of the compound 2 showed polymeric 5-coordinate trigonal bipyramidal geometry. Antimicrobial studies were also evaluated against different strains of bacteria (Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis and Staphylococcus aureus) and fungi (Mucor species, Aspergillus solani, Helminthosporium oryzae, Aspergillus flavus, Aspergillus niger) to establish the biological significance of these compounds. The synthesized compounds probably work by interfering with the ability of bacteria to form cell walls by keeping unwanted substances from entering their cells and stop the contents of their cells from leaking out due which the bacteria get die. The antifungal activity of some of the tested compound is comparable to that of the standard drug, terbinafine. From their antimicrobial results, it was concluded that they might be used as potential candidate for the generation of new antimicrobial drugs.

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Acknowledgments

The authors are thankful to higher education commission of Pakistan for financial support during the present study.

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Authors and Affiliations

  1. Allama Iqbal Open University Islamabad, Islamabad, Pakistan

    Farzana Shaheen

  2. Department of Chemistry, University of Science and Technology Bannu, Bannu, 28100, Pakistan

    Muhammad Sirajuddin

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

    Saqib Ali & Ali Haider

  4. Ecole Polytechnique Fédérale de Lausanne Institut Des Sciences et Ingénierie Chimiques EPFL SB ISIC LCOM, BCH 2402 (Batochime), 1015, Lausanne, Switzerland

    Paul Joseph Dyson

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

    Muhammad Nawaz Tahir

  6. Department of Pharmaceutical Chemistry, Riphah Institute of Pharmaceutical Sciences, Riphah International University, Islamabad, Pakistan

    Khadija Shahid

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  1. Farzana Shaheen
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  2. Muhammad Sirajuddin
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  3. Saqib Ali
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  4. Paul Joseph Dyson
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  5. Ali Haider
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Corresponding authors

Correspondence to Muhammad Sirajuddin or Saqib Ali.

Supplementary material

Supplementary material

Crystallographic data for complex 2 reported in this paper have been deposited with the Cambridge Crystallographic Data Centre, CCDC# 1447182. Copies of this information may be obtained free of charge from the Director, CCDC, 12, Union Road, Cambridge CB2 1EZ [Fax: +44 1223 336 033] or deposit@ccdc.cam.ac.uk or http://www.ccdc.cam.ac.uk.

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Shaheen, F., Sirajuddin, M., Ali, S. et al. Synthesis, structural elucidation and biological activities of organotin(IV) derivatives of 4-(2-thienyl)butyric acid. J IRAN CHEM SOC 14, 387–394 (2017). https://doi.org/10.1007/s13738-016-0987-7

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  • DOI: https://doi.org/10.1007/s13738-016-0987-7

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