Design, Synthesis, and Biological Evaluation of New Indole-Acrylamide-1,2,3-Triazole Derivatives as Potential α-Glucosidase Inhibitors

Sadat-Ebrahimi, Seyed Esmaeil; Babania, Hiva; Mohammadi‐Khanaposhtani, Maryam; Asgari, Mohammad; Mojtabavi, Somayeh; Faramarzi, Mohammad Ali; Yahya-Meymandi, Azadeh; Zareie, Samaneh; Larijani, Bagher; Biglar, Mahmoud; Rastgar, Hossein; Foroumadi, Alireza; Mahdavi, Mohammad

doi:10.1080/10406638.2020.1854323

Cited by 9 publications

(3 citation statements)

References 25 publications

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“…Anticancer activity [81] Indole-acrylamide analogs coupled with aromatic azides CuAAC Enzyme (α-glucosidase) inhibitory activity [82] Thiosemicarbazone analogs coupled with aromatic azides…”

Section: Cuaacmentioning

confidence: 99%

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

Halay

Açıkbaş

2023

ACE

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Click chemistry is totally an approach consisting of efficient and reliable reactions that bind two molecular building blocks and require no complex purification techniques. The aspire of achieving molecules with the desired characteristics and behaviour is the key to the click chemistry concept. In this concept, in order to obtain 1,2,3-triazole products as diversely functionalized molecules, copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction has been widely used for years in the field of materials science, organic synthesis and the biochemistry. This review focusses on the importance of click chemistry for obtaining biologically active triazole molecules and therefore the applications of such 1,2,3-triazole derivatives in medicinal chemistry field are highlighted.

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Section: Cuaacmentioning

confidence: 99%

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

Halay

Açıkbaş

2023

ACE

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“…Increased glucose level occurs in the blood due to diabetes, which can lead to serious side effects such as coronary heart disease, stroke, liver damage, nephropathy, retinopathy, and peripheral nephropathy over time . Furthermore, both the oral cavity and small intestine contain a variety of digestive enzymes that are involved in starch hydrolysis. , Among them, α-glucosidase is synthesized through a fast and efficient method, − as well as α-amylase plays a crucial role in regulating the postprandial glucose concentration, so they are considered necessary enzymes for the digestion of starch and glycogen, respectively. Inhibiting either α-glucosidase or α-amylase is therefore a successful strategy to reduce postprandial hyperglycemia.…”

Section: Introductionmentioning

confidence: 99%

Molecular Modeling and Synthesis of Indoline-2,3-dione-Based Benzene Sulfonamide Derivatives and Their Inhibitory Activity against α-Glucosidase and α-Amylase Enzymes

et al. 2023

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Diabetes is also known as a critical and noisy disease. Hyperglycemia, that is, increased blood glucose level is a common effect of uncontrolled diabetes, and over a period of time can cause serious effects on health such as blood vessel damage and nervous system damage. However, many attempts have been made to find suitable and beneficial solutions to overcome diabetes. Considering this fact, we synthesized a novel series of indoline-2,3-dione-based benzene sulfonamide derivatives and evaluated them against α-glucosidase and α-amylase enzymes. Out of the synthesized sixteen compounds (1–16), only three compounds showed better results; the IC50 value was in the range of 12.70 ± 0.20 to 0.90 ± 0.10 μM for α-glucosidase against acarbose 11.50 ± 0.30 μM and 14.90 ± 0.20 to 1.10 ± 0.10 μM for α-amylase against acarbose 12.20 ± 0.30 μM. Among the series, only three compounds showed better inhibitory potential such as analogues 11 (0.90 ± 0.10 μM for α-glucosidase and 1.10 ± 0.10 μM for α-amylase), 1 (1.10 ± 0.10 μM for α-glucosidase and 1.30 ± 0.10 μM for α-amylase), and 6 (1.20 ± 0.10 μM for α-glucosidase and 1.60 ± 0.10 μM for α-amylase). Molecular modeling was performed to determine the binding affinity of active interacting residues against these enzymes, and it was found that benzenesulfonohydrazide derivatives can be indexed as suitable inhibitors for diabetes mellitus.

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“…In this regards, several series of synthetic indole or bisindole based α-glucosidase inhibitors have been introduced (Fig. 1, compounds F-J) [22][23][24][25][26].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, in vitro, and in silico biological evaluations of new coumarin-indole hybrids as anti-α-glucosidase agents

Niri

Sayahi

Behrouz

et al. 2022

Preprint

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Background A new series of coumarin-indole hybrids was designed and synthesized as novel anti-diabetic agents through inhibition of α-glucosidase, which is an important anti-diabetic target. The title hybrids were designed based on hybridization of two active pharmacophors against α-glucosidase: coumarin and indole. Methods The thirteen various derivatives 4a-m were synthesized, purified, and fully characterized. These compounds were evaluated against α-glucosidase in vitro and in silico. In silico pharmacokinetic study of the most potent compounds was also performed. Results Most of the title compounds exhibited high anti-α-glucosidase activity in comparison to standard drug acarbose. In particular, the phenoxy derivative 4d namely 3-((1H-indol-3-yl)(3-phenoxyphenyl)methyl)-4-hydroxy-2H-chromen-2-one showed promising activity. This compound is a competitive inhibitor into α-glucosidase and showed the lowest binding energy at α-glucosidase active site in comparison to other potent newly synthesized compounds and acarbose. Conclusion Compound 4d can be a lead compound for further structural development to obtain an effective and potent α-glucosidase inhibitor.

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Design, Synthesis, and Biological Evaluation of New Indole-Acrylamide-1,2,3-Triazole Derivatives as Potential α-Glucosidase Inhibitors

Cited by 9 publications

References 25 publications

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

Click chemistry: A fascinating, Nobel-winning method for the improvement of biological activity

Molecular Modeling and Synthesis of Indoline-2,3-dione-Based Benzene Sulfonamide Derivatives and Their Inhibitory Activity against α-Glucosidase and α-Amylase Enzymes

Design, synthesis, in vitro, and in silico biological evaluations of new coumarin-indole hybrids as anti-α-glucosidase agents

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