Synthesis, In Vitro Evaluation and Molecular Docking of the 5-Acetyl-2-aryl-6-hydroxybenzo[b]furans against Multiple Targets Linked to Type 2 Diabetes.

Biomolecules
Malose J MphahleleSamantha Gildenhuys

Abstract

The 5-acetyl-2-aryl-6-hydroxybenzo[b]furans 2a-h have been evaluated through in vitro enzymatic assay against targets which are linked to type 2 diabetes (T2D), namely, α-glucosidase, protein tyrosine phosphatase 1B (PTP1B) and β-secretase. These compounds have also been evaluated for antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical scavenging method. The most active compounds against α-glucosidase and/or PTP1B, namely, 4-fluorophenyl 2c, 4-methoxyphenyl 2g and 3,5-dimethoxyphenyl substituted 2h derivatives were also evaluated for potential anti-inflammatory properties against cyclooxygenase-2 activity. The Lineweaver-Burk and Dixon plots were used to determine the type of inhibition on compounds 2c and 2h against α-glucosidase and PTP1B receptors. The interactions were investigated in modelled complexes against α-glucosidase and PTP1B via molecular docking.

References

Mar 5, 1992·Nature·R LüthyD Eisenberg
Dec 5, 1993·Journal of Molecular Biology·A Sali, T L Blundell
Dec 1, 1996·Critical Reviews in Biochemistry and Molecular Biology·N SekarY Shechter
Mar 15, 2001·Current Opinion in Cell Biology·N K Tonks, B G Neel
Sep 5, 2002·Nature Reviews. Drug Discovery·Andrew L Hopkins, Colin R Groom
Apr 3, 2003·Journal of the American Chemical Society·Bruce G SzczepankiewiczMichael R Jirousek
Nov 7, 2003·The Journal of Clinical Endocrinology and Metabolism·Mary F CarrollDavid S Schade
Dec 31, 2003·Methods in Enzymology·András Fiser, Andrej Sali
May 4, 2004·Chembiochem : a European Journal of Chemical Biology·Hans-Joachim BöhmMartin Stahl
Jun 25, 2004·Nucleic Acids Research·Burkhard RostJinfeng Liu
Jul 20, 2004·Nature Structural & Molecular Biology·Christian WiesmannStig K Hansen
Dec 9, 2004·Bioinformatics·Gianluca Pollastri, Aoife McLysaght
Jan 6, 2005·Molecular and Cellular Biology·Sandra GalicTony Tiganis
Jun 14, 2005·Bioorganic & Medicinal Chemistry Letters·Manish DixitAtul Goel
Jun 28, 2005·Nucleic Acids Research·J ChengP Baldi
Jul 18, 2006·Nature Medicine·Kendra K BenceBarbara B Kahn
May 1, 2007·Drug Discovery Today·Sheng Zhang, Zhong-Yin Zhang
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Jun 24, 2008·Journal of Medicinal Chemistry·William K Hagmann
Aug 15, 2012·Journal of Cheminformatics·Marcus D HanwellGeoffrey R Hutchison
Oct 25, 2012·Diabetes, Metabolic Syndrome and Obesity : Targets and Therapy·Christoph Rosak, Gabriele Mertes
Mar 16, 2013·Current Diabetes Reports·Eric Lontchi-YimagouAndre Pascal Kengne
Jun 12, 2013·Nucleic Acids Research·Daniel W A BuchanDavid T Jones
Dec 3, 2014·European Journal of Medicinal Chemistry·Ravi NaikKyeong Lee
Dec 9, 2014·European Journal of Medicinal Chemistry·Hena Khanam, Shamsuzzaman
Mar 3, 2015·European Journal of Medicinal Chemistry·Jung-Feng HsiehWen-Tai Li
Apr 18, 2015·Nucleic Acids Research·Alexey DrozdetskiyGeoffrey J Barton
Feb 9, 2017·Biochemistry Research International·Zhi-Long ShiZhao-Xiang Yang
May 5, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ariana PicuMariana Carmen Chifiriuc
May 13, 2017·ChemMedChem·Zhiyang Liu, Shutao Ma
Jun 7, 2017·Chemical Biology & Drug Design·Alexander A SpasovYuri N Klimochkin
Sep 22, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Yeong Hun SongKi Hun Park
Nov 18, 2017·Current Opinion in Structural Biology·Paweł Śledź, Amedeo Caflisch
Apr 4, 2018·Nature Communications·Paul J MeakinFranck Peiretti
Jan 16, 2019·Diabetes & Metabolic Syndrome·Akram AhangarpourMiaad Sayahi
May 11, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Wen-Jia DanJin-Ming Gao
Jun 14, 2019·Evidence-based Complementary and Alternative Medicine : ECAM·Siba ShanakHilal Zaid
Aug 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Srijan ShresthaJae Sue Choi
Nov 7, 2019·Bioinformatics·Anne MorgatUNKNOWN UniProt Consortium

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Citations

Sep 2, 2020·European Journal of Medicinal Chemistry·Antonios KousaxidisAthina Geronikaki
Aug 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Massimo GenovesePaolo Paoli

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Methods Mentioned

BETA
column chromatography
nuclear magnetic resonance
silica gel column chromatography
fluorescence
NMR
X-ray
interaction studies

Software Mentioned

MODELLERv9
PSIPRED
AutoDock4
JPred
ProCheck
PORTER
AutoDockTools
Origin Pro
AutoDockTool
SCRATCH

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