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Synthesis and evaluation of novel xanthene-based thiazoles as potential antidiabetic agents.

التفاصيل البيبلوغرافية
العنوان: Synthesis and evaluation of novel xanthene-based thiazoles as potential antidiabetic agents.
المؤلفون: Naseem S; Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan., Shafiq Z; Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan.; Department of Pharmaceutical & Medicinal Chemistry, University of Bonn, Bonn, Germany., Taslimi P; Department of Biotechnology, Faculty of Science, Bartin University, Bartin, Turkey.; Department of Chemistry, Faculty of Science, Istinye University, Istanbul, Turkey., Hussain S; Institute of Chemical Sciences, Bahauddin Zakariya University, Multan, Pakistan., Taskin-Tok T; Department of Chemistry, Faculty of Arts and Sciences, Gaziantep University, Gaziantep, Turkey.; Department of Bioinformatics and Computational Biology, Institute of Health Sciences, Gaziantep University, Gaziantep, Turkey., Kisa D; Department of Molecular Biology and Genetics, Faculty of Science, Bartin University, Bartin, Turkey., Saeed A; Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan., Temirak A; Chemistry of Natural and Microbial Products Department, Pharmaceutical and Drug Industries Research Institute, National Research Centre, Dokki, Cairo, Egypt., Tahir MN; Department of Physics, University of Sargodha, Sargodha, Pakistan., Rauf K; Department of Chemistry, Govt. Post-Graduate Gordon College, Rawalpindi, Pakistan., El-Gokha A; Chemistry Department, Faculty of Science, Menoufia University, Menoufia, Egypt.
المصدر: Archiv der Pharmazie [Arch Pharm (Weinheim)] 2023 Jan; Vol. 356 (1), pp. e2200356. Date of Electronic Publication: 2022 Oct 11.
نوع المنشور: Journal Article
اللغة: English
بيانات الدورية: Publisher: Wiley-VCH Verlag GmbH & Co. KGaA Country of Publication: Germany NLM ID: 0330167 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1521-4184 (Electronic) Linking ISSN: 03656233 NLM ISO Abbreviation: Arch Pharm (Weinheim) Subsets: MEDLINE
أسماء مطبوعة: Publication: <2005->: Weinheim Germany : Wiley-VCH Verlag GmbH & Co. KGaA
Original Publication: Weinheim, Verlag Chemie GmbH.
مواضيع طبية MeSH: Butyrylcholinesterase*/metabolism , Acetylcholinesterase*/metabolism, Hypoglycemic Agents/pharmacology ; Molecular Docking Simulation ; Structure-Activity Relationship ; Thiazoles ; Cholinesterase Inhibitors/chemistry ; Glycoside Hydrolases/metabolism
مستخلص: A series of xanthene-based thiazoles was synthesized and characterized by different scpectroscopic methods, i.e. Proton nuclear magnetic resonance ( 1 H NMR), carbon nuclear magnetic resonance ( 13 C NMR), infrared spectroscopy, carbon hydrogen nitrogen analysis, and X-ray crystallography. The inhibition potencies of 18 newly synthesized thiazole derivatives were investigated on the activities of acetylcholinesterase (AChE), butyrylcholinesterase (BChE), α-amylase (α-Amy), and α-glycosidase (α-Gly) enzymes in accordance with their antidiabetic and anticholinesterase ability. The synthesized compounds have the highest inhibition potential against the enzymes at low nanomolar concentrations. Among the 18 newly synthesized molecules, 3b and 3p were superior to the known commercial inhibitors of the enzymes and have a much more effective inhibitory potential, with IC 50 : 2.37 and 1.07 nM for AChE, 0.98 and 0.59 nM for BChE, 56.47 and 61.34 nM for α-Gly, and 152.48 and 124.84 nM for α-Amy, respectively. Finally, the optimized 18 compounds were subjected to molecular docking to describe the interaction between thiazole derivatives and AChE, BChE, α-Amy, and α-Gly enzymes in which important interactions were monitored with amino acid residues of each target enzyme.
(© 2022 Deutsche Pharmazeutische Gesellschaft.)
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معلومات مُعتمدة: 6975/NRPU/R&D Z. S. is thankful to Higher Education Commission (HEC), Islamabad, Pakistan
فهرسة مساهمة: Keywords: cholinesterase; molecular docking; thiazoline; xanthene; α-amylase; α-glycosidase
المشرفين على المادة: EC 3.1.1.8 (Butyrylcholinesterase)
EC 3.1.1.7 (Acetylcholinesterase)
0 (Hypoglycemic Agents)
0 (Thiazoles)
0 (Cholinesterase Inhibitors)
EC 3.2.1.- (Glycoside Hydrolases)
تواريخ الأحداث: Date Created: 20221011 Date Completed: 20230103 Latest Revision: 20230103
رمز التحديث: 20240628
DOI: 10.1002/ardp.202200356
PMID: 36220614
قاعدة البيانات: MEDLINE
الوصف
تدمد:1521-4184
DOI:10.1002/ardp.202200356