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Vol. 36 No. 10 (2024): Vol 36 Issue 10, 2024

Copyright (c) 2024 Vasudeva Rao Avupati

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Synthesis and in vitro Biological Evaluation of a Series of 5-Benzylidene Derivatives of Rhodanine-Sulfonylurea Hybrid as a Novel Class of α-Glucosidase Inhibitors

https://doi.org/10.14233/ajchem.2024.32383
Asha Nandini Suresh
School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0006-2859-3399
Adam Sammuel Anak Luang
School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0005-9302-497X
Michelle Chai Yet Ling
School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0005-9513-665X
Thishaa Nair Selvam
School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0009-0006-7347-9296
Vasudeva Rao Avupati
Department of Pharmaceutical Chemistry, School of Pharmacy, IMU University (Formerly known as International Medical University), 126, Jalan Jalil Perkasa 19, Bukit Jalil, 57000 Kuala Lumpur, Malaysia
https://orcid.org/0000-0003-0899-513X

Corresponding Author(s) : Vasudeva Rao Avupati

vasudevaraoavupati@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 10 (2024): Vol 36 Issue 10, 2024

Abstract

A novel rhodanine-sulfonylurea hybrid (C) has been prepared based on the isocyanate-amine reaction conditions in the first step and its 5-benzylidene analogues (C1-C13) were synthesized using Knoevenagel reaction conditions as the subsequent step. The physical and spectral characterization of all the synthesized compounds (C-C13) was performed using FT-IR, 1H NMR and HR-ESI-MS spectral methods. All compounds were subjected to in vitro α-glucosidase enzyme inhibitory properties at 100 µM concentration. The results were compared with a standard drug, voglibose, also tested at the similar concentrations. The bioassay results revealed that the intermediate compound C was more potent with a percentage inhibitory activity of 64.86%, which is relatively better than the series of 5-benzylidene analogues (C1-C13) synthesized from the intermediate C. This clearly displayed that substitution at position-5 on the rhodanine ring of intermediate C is not a favourable substitution to enhance the bioactivity; however, one of the derivative compounds, C12, has exhibited potency of 58.32%, which is close to the compound C. It is significant that both the intermediate C and compound C12 displayed better potency compared to the standard voglibose, with percentage inhibition recorded at 37.75%. The additive or synergistic potential of the bioactive pharmacophore tosylurea, which was earlier established, tolerated the rhodanine ring substitution towards retaining the α-glucosidase inhibitory properties.

Keywords

Rhodanine Sulfonylurea Rhodanine-Sulfonylurea hybrid 5-Bezylidene-rhodanine α-Glucosidase inhibitor
Suresh, A. N., Anak Luang, A. S., Yet Ling, M. C., Selvam, T. N., & Avupati, V. R. (2024). Synthesis and in vitro Biological Evaluation of a Series of 5-Benzylidene Derivatives of Rhodanine-Sulfonylurea Hybrid as a Novel Class of α-Glucosidase Inhibitors. Asian Journal of Chemistry, 36(10), 2467–2474. https://doi.org/10.14233/ajchem.2024.32383
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