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Synthesis, α-amylase inhibition and molecular docking study of bisindolylmethane sulfonamide derivatives

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Abstract

We have synthesized nineteen (1–19) bisindolylmethane sulfonamide analogs, characterized by different spectroscopic techniques such as 1HNMR and EI-MS and tested for α-amylase inhibitory potential. All compounds showed excellent to moderate degree of α-amylase inhibitory potential with IC50 values ranging between 1.192 ± 0.51 to 3.057 ± 0.18 μM as equated with standard acarbose (IC50 values 0.83 ± 0.36 μM). Among the series, six analogs such as 1, 4, 5, 6, 10, and 14 showed potent α-amylase inhibition with IC50 values 1.747 ± 0.2, 1.208 ± 0.15, 1.192 ± 0.51, 1.858 ± 0.08, 1.358 ± 0.27 and 1.527 ± 0.17 μM, respectively, as equated with standard acarbose. The structure-activity relationship based upon different substituents on phenyl part. Molecular docking studies performed to recognize the binding interaction of the most active compounds.

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Acknowledgements

We would like to thank IRMC and Imam Abdulrahman Bin Faisal University for Lab facilities.

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Authors and Affiliations

  1. Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), University of Dammam, Dammam, 31441, Saudi Arabia

    Muhammad Taha & Ashik Mosaddik

  2. Department of Chemistry, University of Wah, Quaid Avenue, Wah Cantt, 47000, Pakistan

    Tayyaba Noreen & Fasial Nawaz

  3. Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300, Bandar Puncak Alam, Selangor, Malaysia

    Tayyaba Noreen, Syahrul Imran & Nor Hadiani Ismail

  4. Faculty of Applied Science, UiTM Shah Alam, 40450, Shah Alam, Selangor D.E., Malaysia

    Syahrul Imran & Nor Hadiani Ismail

  5. Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, Qassim University, Buraidah, 51452, Saudi Arabia

    Sridevi Chigurupati

  6. School of Engineering, Monash University (Malaysia Campus), Bandar Sunway, 47500, Malaysia

    Manikandan Selvaraj

  7. Department of Chemistry, Hazara University, Mansehra, 21300, Khyber Pakhtunkhwa, Pakistan

    Fazal Rahim

  8. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, AIMST University, Semeling, 08100, Bedong, Kedah, Malaysia

    Ashok Kumar

  9. Management Information Systems, College of Applied Studies and Community Service, Imam Abdulrahman Bin Faisal University, P.O. Box. 1982, Dammam, 31441, Saudi Arabia

    Abdullah M. Alghamdi

  10. King Fahad specialist hospital in Dammam, (general surgery resident), Dammam, 31441, Saudi Arabia

    Yousif Abdulrahman nasser alqahtani

  11. College of Medicine Imam Abdulrahman Bin Faisal University, P.O. Box. 1982, Dammam, 31441, Saudi Arabia

    Abdulaziz Abdulrahman nasser alqahtani

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  1. Muhammad Taha
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  2. Tayyaba Noreen
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  3. Syahrul Imran
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  11. Abdullah M. Alghamdi
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  12. Yousif Abdulrahman nasser alqahtani
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  13. Abdulaziz Abdulrahman nasser alqahtani
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Correspondence to Muhammad Taha.

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Taha, M., Noreen, T., Imran, S. et al. Synthesis, α-amylase inhibition and molecular docking study of bisindolylmethane sulfonamide derivatives. Med Chem Res 28, 2010–2022 (2019). https://doi.org/10.1007/s00044-019-02431-4

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