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Synthesis of Bis-indolylmethane sulfonohydrazides derivatives as potent α-Glucosidase inhibitors

Publication date:

October 2018


Source:Bioorganic Chemistry, Volume 80

Author(s): Mohammed Gollapalli, Muhammad Taha, Hayat Ullah, Muhammad Nawaz, Laode Muhammad Ramadhan AlMuqarrabun, Fazal Rahim, Faiza Qureshi, Ashik Mosaddik, Norizan Ahmat, Khalid Mohammed Khan

In search of better α-glucosidase inhibitors, a series of bis-indolylmethane sulfonohydrazides derivatives (1-14) were synthesized and evaluated for their α-glucosidase inhibitory potential. All derivatives exhibited outstanding α-glucosidase inhibition with IC50 values ranging between 0.10 ± 0.05 to 5.1 ± 0.05 μM when compared with standard drug acarbose having IC50 value 856.28 ± 3.15 μM. Among the series, analog 7 (0.10 ± 0.05 μM) with tri-chloro substitution on phenyl ring was identified as the most potent inhibitor of α-glucosidase (∼ 8500 times). The structure activity relationship has been also established. Molecular docking studies were also performed to help understand the binding interaction of the most active analogs with receptors. From the docking studies, it was observed that all the active bis-indolylmethane sulfonohydrazides derivatives showed considerable binding interactions within the active site (acarbose inhibition site) of α-glucosidase. We also evaluated toxicity of all derivatives and found none of them are toxic.
Graphical abstract




Authors:   Author(s): Mohammed Gollapalli, Muhammad Taha, Hayat Ullah, Muhammad Nawaz, Laode Muhammad Ramadhan AlMuqarrabun, Fazal Rahim, Faiza Qureshi, Ashik Mosaddik, Norizan Ahmat, Khalid Mohammed Khan
Journal:   Bioorganic Chemistry
Volume:   80
Year:   2018
Pages:   112
DOI:   10.1016/j.bioorg.2018.06.001
Publication date:   18-Jun-2018
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