Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles

Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles

Twenty derivatives of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles (1–20) were synthesized and evaluated for their α-glucosidase inhibitory activities. Compounds containing hydroxyl and halogens (1–6, and 8–18) were found to be five to seventy folds more active with IC50 values in the range...

Full description

Bibliographic Details
Published in:Bioorganic Chemistry
Main Author: Taha M.; Ismail N.H.; Imran S.; Wadood A.; Rahim F.; Saad S.M.; Khan K.M.; Nasir A.
Format: Article
Language:English
Published: Academic Press Inc. 2016
Online Access:https://www.scopus.com/inward/record.uri?eid=2-s2.0-85008612459&doi=10.1016%2fj.bioorg.2016.04.006&partnerID=40&md5=b9d61da322363b367cd5c098bfebb791
id 2-s2.0-85008612459
spelling 2-s2.0-85008612459
Taha M.; Ismail N.H.; Imran S.; Wadood A.; Rahim F.; Saad S.M.; Khan K.M.; Nasir A.
Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
2016
Bioorganic Chemistry
66

10.1016/j.bioorg.2016.04.006
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85008612459&doi=10.1016%2fj.bioorg.2016.04.006&partnerID=40&md5=b9d61da322363b367cd5c098bfebb791
Twenty derivatives of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles (1–20) were synthesized and evaluated for their α-glucosidase inhibitory activities. Compounds containing hydroxyl and halogens (1–6, and 8–18) were found to be five to seventy folds more active with IC50 values in the range of 12.75 ± 0.10–162.05 ± 1.65 μM, in comparison with the standard drug, acarbose (IC50 = 856.45 ± 5.60 μM). Current study explores the α-glucosidase inhibition of a hybrid class of compounds of oxadiazole and benzofurans. These findings may invite researchers to work in the area of treatment of hyperglycemia. Docking studies showed that most compounds are interacting with important amino acids Glu 276, Asp 214 and Phe 177 through hydrogen bonds and arene-arene interaction. © 2016 Elsevier Inc.
Academic Press Inc.
452068
English
Article
author Taha M.; Ismail N.H.; Imran S.; Wadood A.; Rahim F.; Saad S.M.; Khan K.M.; Nasir A.
spellingShingle Taha M.; Ismail N.H.; Imran S.; Wadood A.; Rahim F.; Saad S.M.; Khan K.M.; Nasir A.
Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
author_facet Taha M.; Ismail N.H.; Imran S.; Wadood A.; Rahim F.; Saad S.M.; Khan K.M.; Nasir A.
author_sort Taha M.; Ismail N.H.; Imran S.; Wadood A.; Rahim F.; Saad S.M.; Khan K.M.; Nasir A.
title Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
title_short Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
title_full Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
title_fullStr Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
title_full_unstemmed Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
title_sort Synthesis, molecular docking and α-glucosidase inhibition of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles
publishDate 2016
container_title Bioorganic Chemistry
container_volume 66
container_issue
doi_str_mv 10.1016/j.bioorg.2016.04.006
url https://www.scopus.com/inward/record.uri?eid=2-s2.0-85008612459&doi=10.1016%2fj.bioorg.2016.04.006&partnerID=40&md5=b9d61da322363b367cd5c098bfebb791
description Twenty derivatives of 5-aryl-2-(6′-nitrobenzofuran-2′-yl)-1,3,4-oxadiazoles (1–20) were synthesized and evaluated for their α-glucosidase inhibitory activities. Compounds containing hydroxyl and halogens (1–6, and 8–18) were found to be five to seventy folds more active with IC50 values in the range of 12.75 ± 0.10–162.05 ± 1.65 μM, in comparison with the standard drug, acarbose (IC50 = 856.45 ± 5.60 μM). Current study explores the α-glucosidase inhibition of a hybrid class of compounds of oxadiazole and benzofurans. These findings may invite researchers to work in the area of treatment of hyperglycemia. Docking studies showed that most compounds are interacting with important amino acids Glu 276, Asp 214 and Phe 177 through hydrogen bonds and arene-arene interaction. © 2016 Elsevier Inc.
publisher Academic Press Inc.
issn 452068
language English
format Article
accesstype
record_format scopus
collection Scopus
_version_ 1809678486051225600

Similar Items