Synthesis and biological evaluation of α,α-difluorobenzylphosphonic acid derivatives as small molecular inhibitors of protein-tyrosine phosphatase 1B
A series of α,α-difluorobenzylphosphonic acids having a hydrophobic functional group were prepared via the Stille coupling reaction from halogenated α,α-difluorobenzylphosphonates. Evaluation of inhibitory activity toward protein tyrosine phosphatase (PTP 1B) revealed that the ethynyl, phenylethynyl...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 1999-02, Vol.9 (4), p.529-532 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Yokomatsu, Tsutomu Murano, Tetsuo Umesue, Ikuko Soeda, Shinji Shimeno, Hiroshi Shibuya, Shiroshi |
| description | A series of α,α-difluorobenzylphosphonic acids having a hydrophobic functional group were prepared
via the Stille coupling reaction from halogenated α,α-difluorobenzylphosphonates. Evaluation of inhibitory activity toward protein tyrosine phosphatase (PTP 1B) revealed that the ethynyl, phenylethynyl and (
E)-styryl groups on the benzene nuclei increased the inhibitory activity of α,α-difluorobenzylphosphonic acid. Inhibitory activities significantly increased upon introducing both (
E)-styryl and bis-methylsulfonamide functional groups onto the benzene nuclei of α,α-difluorobenzylphosphonic acid.
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| doi_str_mv | 10.1016/S0960-894X(99)00027-X |
| format | Article |
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via the Stille coupling reaction from halogenated α,α-difluorobenzylphosphonates. Evaluation of inhibitory activity toward protein tyrosine phosphatase (PTP 1B) revealed that the ethynyl, phenylethynyl and (
E)-styryl groups on the benzene nuclei increased the inhibitory activity of α,α-difluorobenzylphosphonic acid. Inhibitory activities significantly increased upon introducing both (
E)-styryl and bis-methylsulfonamide functional groups onto the benzene nuclei of α,α-difluorobenzylphosphonic acid.
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via the Stille coupling reaction from halogenated α,α-difluorobenzylphosphonates. Evaluation of inhibitory activity toward protein tyrosine phosphatase (PTP 1B) revealed that the ethynyl, phenylethynyl and (
E)-styryl groups on the benzene nuclei increased the inhibitory activity of α,α-difluorobenzylphosphonic acid. Inhibitory activities significantly increased upon introducing both (
E)-styryl and bis-methylsulfonamide functional groups onto the benzene nuclei of α,α-difluorobenzylphosphonic acid.
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via the Stille coupling reaction from halogenated α,α-difluorobenzylphosphonates. Evaluation of inhibitory activity toward protein tyrosine phosphatase (PTP 1B) revealed that the ethynyl, phenylethynyl and (
E)-styryl groups on the benzene nuclei increased the inhibitory activity of α,α-difluorobenzylphosphonic acid. Inhibitory activities significantly increased upon introducing both (
E)-styryl and bis-methylsulfonamide functional groups onto the benzene nuclei of α,α-difluorobenzylphosphonic acid.
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| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Antineoplastic agents Biological and medical sciences enzyme inhibitors Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology General aspects isosteres Medical sciences mimetics Molecular Structure Organophosphonates - chemical synthesis Organophosphonates - chemistry Organophosphonates - pharmacology Pharmacology. Drug treatments phosphonic acids and derivs Protein Tyrosine Phosphatases - antagonists & inhibitors substitutent effects |
| title | Synthesis and biological evaluation of α,α-difluorobenzylphosphonic acid derivatives as small molecular inhibitors of protein-tyrosine phosphatase 1B |
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