5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors.

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Tytuł:: 5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors.
Autorzy:: Niu T; College of Medicine, Yanbian University, Yanji 133000, China; China-Japan Union Hospital of Jilin University, Changchun 130033, China.
Wang P; National Center for Drug Screening, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Science, Chinese Academy of Sciences, Shanghai 201203, China.
Li C; College of Medicine, Yanbian University, Yanji 133000, China; Department of Pharmacy, Yanbian University Hospital, Yanji 133000, China.
Dou T; College of Pharmacy, Yanbian University, Yanji 133000, China.
Piao H; College of Pharmacy, Yanbian University, Yanji 133000, China.
Li J; National Center for Drug Screening, Shanghai Institute of Materia Medica, Shanghai Institutes for Biological Science, Chinese Academy of Sciences, Shanghai 201203, China. Electronic address: .
Sun L; College of Medicine, Yanbian University, Yanji 133000, China; College of Pharmacy, Yanbian University, Yanji 133000, China. Electronic address: .
Źródło:: Bioorganic chemistry [Bioorg Chem] 2021 Jan; Vol. 106, pp. 104483. Date of Electronic Publication: 2020 Nov 19.
Typ publikacji:: Journal Article; Research Support, Non-U.S. Gov't
Język:: English
Imprint Name(s):: Publication: Amsterdam : Elsevier
Original Publication: New York, London, Academic Press.
MeSH Terms:: Enzyme Inhibitors/*pharmacology
Furans/*pharmacology
Isoleucine/*pharmacology
Phenylalanine/*pharmacology
Protein Tyrosine Phosphatase, Non-Receptor Type 1/*antagonists & inhibitors
Rhodanine/*pharmacology
Dose-Response Relationship, Drug ; Enzyme Inhibitors/chemical synthesis ; Enzyme Inhibitors/chemistry ; Furans/chemical synthesis ; Furans/chemistry ; Humans ; Isoleucine/chemistry ; Molecular Structure ; Phenylalanine/chemistry ; Protein Tyrosine Phosphatase, Non-Receptor Type 1/metabolism ; Rhodanine/chemistry ; Structure-Activity Relationship
Contributed Indexing:: Keywords: Furan; Isoleucine; PTP1B inhibitor; Phenylalanine; Rhodanine
Substance Nomenclature:: 0 (Enzyme Inhibitors)
0 (Furans)
04Y7590D77 (Isoleucine)
47E5O17Y3R (Phenylalanine)
7O50LKL2G8 (Rhodanine)
EC 3.1.3.48 (PTPN1 protein, human)
EC 3.1.3.48 (Protein Tyrosine Phosphatase, Non-Receptor Type 1)
Entry Date(s):: Date Created: 20201203 Date Completed: 20210908 Latest Revision: 20210908
Update Code:: 20240104
DOI:: 10.1016/j.bioorg.2020.104483
PMID:: 33268007
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Two series of 5-aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, 5g was found to have the best PTP1B inhibitory potency (IC 50 = 2.66 ± 0.16 µM) and the best cell division cycle 25 homolog B (CDC25B) inhibitory potency (IC 50 = 0.25 ± 0.02 µM). Enzymatic data together with molecular modeling results demonstrated that the introduction of a sec-butyl group at the 2-position of the carboxyl group remarkably improved the PTP1B inhibitory activity.
(Copyright © 2020 Elsevier Inc. All rights reserved.)

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