Identification of benzothiazole‐rhodanine derivatives as α‐amylase and α‐glucosidase inhibitors: Design, synthesis, in silico, and in vitro analysis

A novel series of benzothiazole‐rhodanine derivatives (A1‐A10) were designed and synthesized, with the aim of developing possible antidiabetic agents and the spectral characterization of these compounds was done using infrared spectroscopy (IR), proton‐nuclear magnetic resonance (1H‐NMR), carbon‐nuc...

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Bibliographic Details
Published in:Journal of molecular recognition 2022-08, Vol.35 (8), p.e2959-n/a
Main Authors: Srinivasa, Mahendra Gowdru, Aggarwal, Natasha Naval, Gatpoh, Banylla Felicity Dkhar, Shankar, Madan Kumar, Byadarahalli Ravindranath, Kannika, Gurubasavaraj Veeranna, Pujar, Dixit, Sheshagiri, Mandal, Subhankar P., Bommenahally Ravanappa, Prashantha Kumar, Khanal, Pukar, Bistuvalli Chandrashekarappa, Revanasiddappa
Format: Article
Language:English
Subjects:
Acarbose
Amylases
Benzothiazole
Diabetes mellitus
Dynamic stability
Glucosidase
in silico analysis
Infrared spectroscopy
Mass spectroscopy
Molecular dynamics
NMR
Nuclear magnetic resonance
pharmacophore
Resonance
rhodanines
Stability analysis
α-Amylase
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Summary:A novel series of benzothiazole‐rhodanine derivatives (A1‐A10) were designed and synthesized, with the aim of developing possible antidiabetic agents and the spectral characterization of these compounds was done using infrared spectroscopy (IR), proton‐nuclear magnetic resonance (1H‐NMR), carbon‐nuclear magnetic resonance (C13‐NMR), and high resolution mass spectroscopy (HR‐MS) techniques. In vitro hypoglycemic potential of the compounds was evaluated by performing α‐amylase and α‐glucosidase enzyme inhibitory assays. In addition, these compounds were subjected to in silico analysis. Based on the results, compounds A5, A6, and A9 displayed good activity in comparison with the standard acarbose. Based on Lineweaver‐Burk plots, it was concluded that compounds A5 and A9 displayed competitive type of enzyme inhibition. Molecular dynamic simulations were conducted to evaluate the stability of the ligand‐protein complex by the calculation of the root mean square deviation, root means square fluctuation, and solvent accessible surface area. Graphical illustration that synthesis and characterization benzothiazole‐rhodanine derivatives.
ISSN:0952-3499
1099-1352
DOI:10.1002/jmr.2959