Quinoline- and Isoindoline-Integrated Polycyclic Compounds as Antioxidant, and Antidiabetic Agents Targeting the Dual Inhibition of α-Glycosidase and α-Amylase Enzymes Article Swipe
Mohammed Al‐Ghorbani
,
Osama Alharbi
,
Abdel-Basit Al-Odayni
,
Naaser A. Y. Abduh
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.3390/ph16091222
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.3390/ph16091222
Novel analogs of quinoline and isoindoline containing various heterocycles, such as tetrazole, triazole, pyrazole, and pyridine, were synthesized and characterized using FT-IR, NMR, and mass spectroscopy, and their antioxidant and antidiabetic activities were investigated. The previously synthesized compound 1 was utilized in conjugation with ketone-bearing tetrazole and isoindoline-1,3-dione to synthesize Schiff’s bases 2 and 3. Furthermore, hydrazide 1 was treated with aryledines to provide pyrazoles 4a–c. Compound 5 was obtained by treating 1 with potassium thiocyanate, which was then cyclized in a basic solution to afford triazole 6. On the other hand, pyridine derivatives 7a–d and 8a–d were synthesized using 2-(4-acetylphenyl)isoindoline-1,3-dione via a one-pot condensation reaction with aryl aldehydes and active methylene compounds. From the antioxidant and antidiabetic studies, compound 7d showed significant antioxidant activity with an EC50 = 0.65, 0.52, and 0.93 mM in the free radical scavenging assays (DPPH, ABTS, and superoxide anion radicals). It also displayed noteworthy inhibitory activity against both enzymes α-glycosidase (IC50: 0.07 mM) and α-amylase (0.21 mM) compared to acarbose (0.09 mM α-glycosidase and 0.25 mM for α-amylase), and higher than in the other compounds. During in silico assays, compound 7d exhibited favorable binding affinities towards both α-glycosidase (−10.9 kcal/mol) and α-amylase (−9.0 kcal/mol) compared to acarbose (−8.6 kcal/mol for α-glycosidase and −6.0 kcal/mol for α-amylase). The stability of 7d was demonstrated by molecular dynamics simulations and estimations of the binding free energy throughout the simulation session (100 ns).
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.3390/ph16091222
- https://www.mdpi.com/1424-8247/16/9/1222/pdf?version=1693364639
- OA Status
- gold
- Cited By
- 13
- References
- 83
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4386284233
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W4386284233Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.3390/ph16091222Digital Object Identifier
- Title
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Quinoline- and Isoindoline-Integrated Polycyclic Compounds as Antioxidant, and Antidiabetic Agents Targeting the Dual Inhibition of α-Glycosidase and α-Amylase EnzymesWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2023Year of publication
- Publication date
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2023-08-30Full publication date if available
- Authors
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Mohammed Al‐Ghorbani, Osama Alharbi, Abdel-Basit Al-Odayni, Naaser A. Y. AbduhList of authors in order
- Landing page
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https://doi.org/10.3390/ph16091222Publisher landing page
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https://www.mdpi.com/1424-8247/16/9/1222/pdf?version=1693364639Direct link to full text PDF
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YesWhether a free full text is available
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goldOpen access status per OpenAlex
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https://www.mdpi.com/1424-8247/16/9/1222/pdf?version=1693364639Direct OA link when available
- Concepts
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Chemistry, Isoindoline, ABTS, Quinoline, Stereochemistry, Antioxidant, Tetrazole, Combinatorial chemistry, DPPH, Organic chemistryTop concepts (fields/topics) attached by OpenAlex
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13Total citation count in OpenAlex
- Citations by year (recent)
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2025: 4, 2024: 8, 2023: 1Per-year citation counts (last 5 years)
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83Number of works referenced by this work
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10Other works algorithmically related by OpenAlex
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