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

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

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 characte...

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Published in:Future Medicinal Chemistry
Main Author: Al-Salahi R.; Ahmad R.; Anouar E.; Iwana Nor Azman N.I.; Marzouk M.; Abuelizz H.A.
Format: Article
Language:English
Published: Future Medicine Ltd. 2018
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85051851796&doi=10.4155%2ffmc-2018-0141&partnerID=40&md5=b8383e3ff482a4404b33b01fafc6d37b
id 2-s2.0-85051851796
spelling 2-s2.0-85051851796
Al-Salahi R.; Ahmad R.; Anouar E.; Iwana Nor Azman N.I.; Marzouk M.; Abuelizz H.A.
3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
2018
Future Medicinal Chemistry
10
16
10.4155/fmc-2018-0141
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85051851796&doi=10.4155%2ffmc-2018-0141&partnerID=40&md5=b8383e3ff482a4404b33b01fafc6d37b
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 (IC 50 = 69.20, 59.60, 49.40, 50.20 and 83.20 μM, respectively) compared with the standard acarbose (IC 50 = 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. © 2018 2018 Newlands Press.
Future Medicine Ltd.
17568919
English
Article
author Al-Salahi R.; Ahmad R.; Anouar E.; Iwana Nor Azman N.I.; Marzouk M.; Abuelizz H.A.
spellingShingle Al-Salahi R.; Ahmad R.; Anouar E.; Iwana Nor Azman N.I.; Marzouk M.; Abuelizz H.A.
3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
author_facet Al-Salahi R.; Ahmad R.; Anouar E.; Iwana Nor Azman N.I.; Marzouk M.; Abuelizz H.A.
author_sort Al-Salahi R.; Ahmad R.; Anouar E.; Iwana Nor Azman N.I.; Marzouk M.; Abuelizz H.A.
title 3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
title_short 3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
title_full 3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
title_fullStr 3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
title_full_unstemmed 3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
title_sort 3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study
publishDate 2018
container_title Future Medicinal Chemistry
container_volume 10
container_issue 16
doi_str_mv 10.4155/fmc-2018-0141
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85051851796&doi=10.4155%2ffmc-2018-0141&partnerID=40&md5=b8383e3ff482a4404b33b01fafc6d37b
description 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 (IC 50 = 69.20, 59.60, 49.40, 50.20 and 83.20 μM, respectively) compared with the standard acarbose (IC 50 = 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. © 2018 2018 Newlands Press.
publisher Future Medicine Ltd.
issn 17568919
language English
format Article
accesstype
record_format scopus
collection Scopus
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