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Silica-supported heterogeneous catalysts-mediated synthesis of chalcones as potent urease inhibitors: in vitro and molecular docking studies

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Abstract

We herein report a facile and high yielding protocol for silica-supported heterogeneous catalysts-mediated synthesis of chalcones. A comparison of results of our synthesis with conventional synthetic protocols is also being offered to assess the efficiency of the prepared catalysts. Biological evaluation of the newly synthesized compounds as urease inhibitors was performed. Most of the compounds were found to have potent urease inhibition activity. The chalcone 3-(3-hydroxyphenyl)-1-phenylpropenone was found to be the most potent with percentage inhibition 86.17 ± 0.89 and half maximal inhibitory concentration (IC50) value 11.51 ± 0.03 µM. The molecular docking study emphasized that the same congeners 3-(furan-2-yl)-1-(4-hydroxyphenyl)propenone, 3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)propanone, and 3-[4-(dimethylamino)phenyl]-1-(p-tolyl)propenone showed very good inhibitory potential against urease and show a higher docking scores 5718, 5940, 5596 and an ACE of − 246.66, − 244.79, and − 243.06 kJ/mol, respectively than the control ligand.

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Acknowledgements

The authors are highly grateful to Higher Education Commission (HEC) of Pakistan for funding Dr. Aeysha Sultan under Start-up Research Grant Program (SRGP) for project No 1507, as well as for financial assistance for EIMS and NMR analyses. We are also thankful to Government College University Faisalabad for assistance in FTIR and UV analyses. The authors thank the Researchers Supporting Project number (RSP-2019/6), King Saud University, Riyadh, Saudi Arabia.

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Authors and Affiliations

  1. Department of Chemistry, University of Education, Faisalabad Campus, Faisalabad, Pakistan

    Aeysha Sultan,  Mehr-un-Nisa & Mian Habib Ur Rehman

  2. Nano and Hybrid Materials Laboratory, Department of Physics, Periyar University, 636 011, Salem, India

    Shanavas Shajahan

  3. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh, 11451, Saudi Arabia

    Tansir Ahamad & Saad M. Alshehri

  4. Department of Chemistry, University of Lahore, Lahore, Pakistan

    Noreen Sajjad

  5. Department of Chemistry, Yilditz University of Engineering and Technology, Istanbul, Turkey

    Lokman Torun

  6. Department of Chemistry, Khawaja Ghulam Fareed University of Engineering and Technology, Rahim Yar Khan, Pakistan

    Muhammad Khalid

  7. Facultad de Ingeniería y Tecnología, Universidad San Sebastián, Bellavista 7, 420524, Santiago, Chile

    Roberto Acevedo

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  1. Aeysha Sultan
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  2. Shanavas Shajahan
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Correspondence to Roberto Acevedo.

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Sultan, A., Shajahan, S., Ahamad, T. et al. Silica-supported heterogeneous catalysts-mediated synthesis of chalcones as potent urease inhibitors: in vitro and molecular docking studies. Monatsh Chem 151, 123–133 (2020). https://doi.org/10.1007/s00706-019-02534-z

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  • DOI: https://doi.org/10.1007/s00706-019-02534-z

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