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Synthesis and urease inhibitory activities of benzophenone semicarbazones/thiosemicarbazones

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Abstract

Twenty-five benzophenone semicarbazones and thiosemicarbazones 3–27 were synthesized starting from benzophenones via hydrazones treated with different aryl isocyanates and isothiocyantes under reflux. All synthetic derivatives were evaluated for their urease inhibitory potential. Good to moderate inhibition trend against urease was observed with the IC50 values in the range of 8.7–119.5 µM, when compared with the standard thiourea (IC50 = 21.2 ± 1.3 µM). Compound 15 showed better inhibition than the standard having the IC50 value of 8.7 ± 0.6 µM. Compounds 3, 4, 8, 11–14, 16, and 17 with the IC50 values within the range of 26.1 to 43.6 µM, demonstrated good to moderate activities while compound 9 (IC50 = 119.5 ± 1.6 µM) displayed very weak activity. The enzyme kinetic studies on the most active compounds 15 and 17 were performed to deduce their modes of inhibition and dissociation constants K i.

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Acknowledgements

We are thankful to the Higher Education Commission (HEC) Pakistan for financial support under National Research Grant Program for Universities to Project No. 20–1910.

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Authors and Affiliations

  1. H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi, 75270, Pakistan

    Arshia Arshia, Ajmal Khan, Khalid Mohammed Khan, Syed Muhammad Saad, Sumaira Javaid & M. Iqbal Choudhary

  2. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, 22060, Pakistan

    Ajmal Khan

  3. Department of Chemistry, Federal Urdu University of Arts, Sciences and Technology, Gulshan-e-Iqbal, Science Campus, Karachi, 75300, Pakistan

    Nida Iqbal Siddiqui

  4. PCSIR Laboratories Complex, Karachi, Shahrah-e-Dr Salimuzzaman Siddiqui, Karachi, 75280, Pakistan

    Shahnaz Perveen

  5. Department of Biochemistry, Faculty of Sciences, King Abdulaziz University, Jeddah, 21412, Saudi Arabia

    M. Iqbal Choudhary

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  1. Arshia Arshia
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  2. Ajmal Khan
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  3. Khalid Mohammed Khan
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  4. Syed Muhammad Saad
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  5. Nida Iqbal Siddiqui
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  7. Shahnaz Perveen
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  8. M. Iqbal Choudhary
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Correspondence to Khalid Mohammed Khan or M. Iqbal Choudhary.

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Arshia, A., Khan, A., Khan, K.M. et al. Synthesis and urease inhibitory activities of benzophenone semicarbazones/thiosemicarbazones. Med Chem Res 25, 2666–2679 (2016). https://doi.org/10.1007/s00044-016-1673-0

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  • DOI: https://doi.org/10.1007/s00044-016-1673-0

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