Chalcone derivatives as xanthine oxidase inhibitors: synthesis, binding mode investigation, biological evaluation, and ADMET prediction

Yang, Can; Liu, Yi; Tu, Yanbei; Li, Lizi; Du, Jiana; Yu, Dehong; He, Pei; Wang, Tao; Liu, Yan; Chen, Hao; Li, Yanfang

doi:10.1016/j.bioorg.2022.106320

Cited by 14 publications

(2 citation statements)

References 38 publications

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“…The SAR study revealed that the presence of hydroxyl group at 3th position on ring B of methoxychalcone increase the XO inhibition activity. Furthermore, the in vivo study showed the compound 89 with chalone skeleton could be a lead compound for the XO inhibition and used for the treatment of hyperuricemia 81 (Fig. 22).…”

Section: Recent Advancement In Nitrogen Containing Heterocycles As Xo...mentioning

confidence: 99%

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Singh,

Debnath,

Chawla

et al. 2024

RSC Med. Chem.

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Section: Recent Advancement In Nitrogen Containing Heterocycles As Xo...mentioning

confidence: 99%

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Singh,

Debnath,

Chawla

et al. 2024

RSC Med. Chem.

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“…[23] Keeping all this in mind, there is a hurried and grave need for the discovery of novel XO inhibitors with relatively fewer side effects and related complications. A diverse number of XO inhibitors have been reported by various researchers which includes pyrano [3,2-d]pyrimidines, [24,25] thiazoles, [26] pyrazoles, [27] flavonoids, [28][29][30][31] benzochromenes, [32] chalcones, [33,34] fraxamosides, [35] isocytosines, [36] 2-mercapto-6-phenylpyrimidine-4carboxylic acids, [37] naphtopyrans, [38] and so on.…”

Section: Introductionmentioning

confidence: 99%

Triazole derivatives as potential xanthine oxidase inhibitors: Design, enzyme inhibition potential, and docking studies

Gulati,

Khanna,

Kumar

et al. 2024

Archiv der Pharmazie

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Considerable ingenuity has been shown in the recent years in the discovery of novel xanthine oxidase (XO) inhibitors that fall outside the purine scaffold. The triazole nucleus has been the cornerstone for the development of many enzyme inhibitors for the clinical management of several diseases, where hyperuricemia is one of them. Here, we give a critical overview of significant research on triazole‐based XO inhibitors, with respect to their design, synthesis, inhibition potential, toxicity, and docking studies, done till now. Based on these literature findings, we can expect a burst of modifications on triazole‐based scaffolds in the near future by targeting XO, which will treat hyperuricemics, that is, painful conditions like gout that at present are hard to deal with.

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Xanthine Oxidase Inhibition by Monoterpene‐Chalcone Conjugates from Kaempferia subglobosa and Molecular Docking Insights

Boonsombat,

Jongsomjainuk,

Thongnest

et al. 2024

Chemistry An Asian Journal

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Kaempferia subglobosa is a perennial medicinal plant in the Zingiberaceae family, identified as a new species in January 2024. To uncover the biological benefits of K. subglobosa and its compounds, investigation of the metabolites of the roots and rhizomes, yielded three new monoterpene‐chalcone conjugates, the globosones A–C, representing a rare metabolite group within the Zingiberaceae, along with six known compounds. The biogenetic pathway for the globosones involves an oxidative [3+2] cycloaddition between α‐phellandrene and 4’‐methoxy‐4,2’,6’‐trihydroxychalcone. Biological testing revealed potent xanthine oxidase (XO) inhibition by globosones A and B, with IC50 values of 7.0±1.0 and 3.0±0.2 μM, respectively, surpassing the positive control drug allopurinol (IC50 7.2±0.1 μM). Globosones A–C also showed good aromatase inhibition (IC50 3.0–3.5 μM). Molecular docking studies indicated that globosones A and B may inhibit xanthine oxidase through binding at the FAD domain site. The physicochemical properties of these isolates suggest that they possess characteristics suitable for additional biological assessment in more advanced test systems. This study enhances an understanding of monoterpene‐chalcone conjugate inhibitors of XO, and offers preliminary insights into the metabolites and bioactivities of K. subglobosa, uncovering potent biological activities associated with this newly discovered plant species.

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Chalcone derivatives as xanthine oxidase inhibitors: synthesis, binding mode investigation, biological evaluation, and ADMET prediction

Cited by 14 publications

References 38 publications

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Heterocyclic compounds as xanthine oxidase inhibitors for the management of hyperuricemia: synthetic strategies, structure–activity relationship and molecular docking studies (2018–2024)

Triazole derivatives as potential xanthine oxidase inhibitors: Design, enzyme inhibition potential, and docking studies

Xanthine Oxidase Inhibition by Monoterpene‐Chalcone Conjugates from Kaempferia subglobosa and Molecular Docking Insights

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