Abstract
N-(3,5-Difluoro-4-hydroxyphenyl)benzenesulfonamide (4) and its derivatives 5-7 were prepared as putative bioisosteres of the previously reported aldose reductase inhibitors, which are the N-benzenesulfonylglycine derivatives I-IV. The in vitro aldose reductase inhibitory activity of the prepared compounds is higher than that of the respective glycine derivatives. Furthermore, the parent compound 4 reveals high antioxidant potential. Additionally, the intestine permeability of 4 is determined, and there is initial evidence that there is an operating influx mechanism. Overall, the data indicate that the presented chemotype could serve as a core structure for the design of putative pharmacotherapeutic agents, aiming to the long-term complications of diabetes mellitus.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehyde Reductase / antagonists & inhibitors*
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Aldehyde Reductase / metabolism
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Animals
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Antioxidants / chemical synthesis
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Antioxidants / chemistry
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Antioxidants / pharmacology
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Benzenesulfonamides
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Biphenyl Compounds / metabolism
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Drug Design
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Enzyme Inhibitors / chemical synthesis*
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / pharmacology*
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Eye / drug effects
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Eye / enzymology
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Female
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Fluorine Compounds / chemical synthesis*
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Fluorine Compounds / chemistry
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Fluorine Compounds / pharmacology*
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Hydrazines / metabolism
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Hydroxylation
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Jejunum / drug effects
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Lipid Peroxidation / drug effects
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Male
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Molecular Structure
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Picrates
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Rats
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Structure-Activity Relationship
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Sulfonamides / chemical synthesis*
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Sulfonamides / chemistry
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Sulfonamides / pharmacology*
Substances
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Antioxidants
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Biphenyl Compounds
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Enzyme Inhibitors
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Fluorine Compounds
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Hydrazines
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Picrates
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Sulfonamides
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1,1-diphenyl-2-picrylhydrazyl
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Aldehyde Reductase