3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study

Rashad Al-Salahi, Rohaya Ahmad, Elhassane Anouar, Nor Izzati Iwana Nor Azman, Mohamed Marzouk, Hatem A. Abuelizz

Research output: Contribution to journalArticle

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Abstract

Aim: Using a simple modification on a previously reported synthetic route, 3-benzyl(phenethyl)-2-thioxobenzo[g]quinazolin-4(3H)-ones (1 and 2) were synthesized with high yields. Further transformation of 1 and 2 produced derivatives 3-26, which were structurally characterized based on NMR and MS data, and their in vitro α-glucosidase inhibitory activity was evaluated using Baker's yeast α-glucosidase enzyme. Results: Compounds 2, 4, 8, 12 and 20 exhibited the highest activity (IC50 = 69.20, 59.60, 49.40, 50.20 and 83.20 μM, respectively) compared with the standard acarbose (IC50 = 143.54 μM). Conclusion: A new class of potent α-glucosidase inhibitors was identified, and the molecular docking predicted plausible binding interaction of the targets in the binding pocket of α-glucosidase and rationalized the structure-activity relationship (SARs) of the target compounds.

LanguageEnglish
Pages1889-1905
Number of pages17
JournalFuture Medicinal Chemistry
Volume10
Issue number16
DOIs
Publication statusPublished - Jan 1 2018

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Quinazolines
alpha-Glucosidases
Inhibitory Concentration 50
Acarbose
Structure-Activity Relationship
Saccharomyces cerevisiae
Enzymes
Glycoside Hydrolase Inhibitors

All Science Journal Classification (ASJC) codes

  • Molecular Medicine
  • Pharmacology
  • Drug Discovery

Cite this

3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors : Synthesis and molecular docking study. / Al-Salahi, Rashad; Ahmad, Rohaya; Anouar, Elhassane; Iwana Nor Azman, Nor Izzati; Marzouk, Mohamed; Abuelizz, Hatem A.

In: Future Medicinal Chemistry, Vol. 10, No. 16, 01.01.2018, p. 1889-1905.

Research output: Contribution to journalArticle

Al-Salahi, Rashad ; Ahmad, Rohaya ; Anouar, Elhassane ; Iwana Nor Azman, Nor Izzati ; Marzouk, Mohamed ; Abuelizz, Hatem A. / 3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors : Synthesis and molecular docking study. In: Future Medicinal Chemistry. 2018 ; Vol. 10, No. 16. pp. 1889-1905.
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abstract = "Aim: Using a simple modification on a previously reported synthetic route, 3-benzyl(phenethyl)-2-thioxobenzo[g]quinazolin-4(3H)-ones (1 and 2) were synthesized with high yields. Further transformation of 1 and 2 produced derivatives 3-26, which were structurally characterized based on NMR and MS data, and their in vitro α-glucosidase inhibitory activity was evaluated using Baker's yeast α-glucosidase enzyme. Results: Compounds 2, 4, 8, 12 and 20 exhibited the highest activity (IC50 = 69.20, 59.60, 49.40, 50.20 and 83.20 μM, respectively) compared with the standard acarbose (IC50 = 143.54 μM). Conclusion: A new class of potent α-glucosidase inhibitors was identified, and the molecular docking predicted plausible binding interaction of the targets in the binding pocket of α-glucosidase and rationalized the structure-activity relationship (SARs) of the target compounds.",
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