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Hydroxytriazenes incorporating sulphonamide derivatives: evaluation of antidiabetic, antioxidant, anti-inflammatory activities, and computational study

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Abstract

The existent investigation deals with synthesis, characterization, computational analysis, and biological activities of some hydroxytriazene derivatives containing sulphonamide moiety. The compounds were screened for antidiabetic, antioxidant, and anti-inflammatory activities. The antidiabetic activity was assessed using α-glucosidase and α-amylase inhibition assays with IC50 values ranging from 32.0 to 759.13 μg/mL and 157.77 to 340.47 μg/mL while standard drug acarbose showed IC50 values 12.21 and 69.74 μg/mL, respectively. The antioxidant activity was evaluated using DPPH and ABTS radical scavenging assays with IC50 value ranging from 54.01 to 912.66 μg/mL and 33.22 to 128.11 μg/mL, and standard drug ascorbic acid showed IC50 values 29.12 μg/mL and 69.13 μg/mL, respectively. Anti-inflammatory activity was investigated using the carrageenan-induced paw edema method, where percentage inhibition was up to 93.0 and 98.57 for 2 h and 4 h, respectively, and all the compounds were found to exhibit excellent anti-inflammatory activity. Moreover, prediction of activity spectra for substance and molecular docking were also performed. The PASS prediction hypothesized the potential of the compounds for anti-inflammatory activity, and docking results suggested the best binding pose for compounds 1b and 2b with the least energy value from which compounds can be considered as potent COX-2 inhibitors. Furthermore, possible interactions between hydroxytriazene analogues and the targets of antioxidant NADPH oxidase and antidiabetic human maltase-glucoamylase enzyme have been identified. The HOMO and LUMO analysis revealed charge transfer within the compounds. These findings suggested that the synthesized compounds can be potential agents for the treatment of diabetes and inflammation.

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Materials and methods and all the instrumentation spectra like IR, 1H NMR, 13C NMR, and mass spectra are provided in the SI.

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Acknowledgements

Authors are thankful to SAIF, Chandigarh, India and MNIT, Jaipur, India for providing spectral analysis.

Funding

P.K. Baroliya acknowledges the financial support from the Science and Engineering Research Board, Government of India, for the award of the TARE grant (TAR/2018/000282).

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Authors and Affiliations

  1. Department of Chemistry, Mohanlal Sukhadia University, Udaipur, India

    Laxmi K. Chauhan, Jaishri Chopra, Ajay K. Goswami & Prabhat K. Baroliya

  2. Department of Medicinal and Pharmaceutical Chemistry, Sree Vidyanikethan College of Pharmacy, Tirupathi, India

    Murugesan Vanangamudi

  3. Amity Institute of Pharmacy (AIP), Amity University Madhya Pradesh (AUMP), Gwalior, India

    Murugesan Vanangamudi

  4. Department of Environmental Sciences, Mahatma Gandhi Gramoday Chitrakoot Vishwavidyalaya, Chitrakoot, Satna, India

    Indra P. Tripathi

  5. Department of Pharmacology and Toxicology Studies, Bhupal Noble Institute of Pharmaceutical Sciences, Udaipur, India

    Amit Bhargava

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Chauhan, L.K., Chopra, J., Vanangamudi, M. et al. Hydroxytriazenes incorporating sulphonamide derivatives: evaluation of antidiabetic, antioxidant, anti-inflammatory activities, and computational study. Mol Divers 27, 223–237 (2023). https://doi.org/10.1007/s11030-022-10420-w

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