Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor.
Publication
, Journal Article
Han, Y; Belley, M; Bayly, CI; Colucci, J; Dufresne, C; Giroux, A; Lau, CK; Leblanc, Y; McKay, D; Therien, M; Wilson, M-C; Skorey, K ...
Published in: Bioorganic & medicinal chemistry letters
June 2008
A series of quinoline/naphthalene-difluoromethylphosphonates were prepared and were found to be potent PTP1B inhibitors. Most of these compounds bearing polar functionalities or large lipophilic residues did not show appreciable oral bioavailability in rodents while small and less polar analogs displayed moderate to good oral bioavailability. The title compound was found to have the best overall potency and pharmacokinetic profile and was found to be efficacious in animal models of diabetes and cancer.
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Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
June 2008
Volume
18
Issue
11
Start / End Page
3200 / 3205
Related Subject Headings
- Rats
- Protein Tyrosine Phosphatase, Non-Receptor Type 1
- Organophosphonates
- Neoplasms
- Naphthalenes
- Molecular Structure
- Mice
- Medicinal & Biomolecular Chemistry
- Hydrocarbons, Halogenated
- Haplorhini
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Han, Y., Belley, M., Bayly, C. I., Colucci, J., Dufresne, C., Giroux, A., … Kennedy, B. P. (2008). Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor. Bioorganic & Medicinal Chemistry Letters, 18(11), 3200–3205. https://doi.org/10.1016/j.bmcl.2008.04.064
Han, Yongxin, Michel Belley, Christopher I. Bayly, John Colucci, Claude Dufresne, Andre Giroux, Cheuk K. Lau, et al. “Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor.” Bioorganic & Medicinal Chemistry Letters 18, no. 11 (June 2008): 3200–3205. https://doi.org/10.1016/j.bmcl.2008.04.064.
Han Y, Belley M, Bayly CI, Colucci J, Dufresne C, Giroux A, et al. Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor. Bioorganic & medicinal chemistry letters. 2008 Jun;18(11):3200–5.
Han, Yongxin, et al. “Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor.” Bioorganic & Medicinal Chemistry Letters, vol. 18, no. 11, June 2008, pp. 3200–05. Epmc, doi:10.1016/j.bmcl.2008.04.064.
Han Y, Belley M, Bayly CI, Colucci J, Dufresne C, Giroux A, Lau CK, Leblanc Y, McKay D, Therien M, Wilson M-C, Skorey K, Chan C-C, Scapin G, Kennedy BP. Discovery of [(3-bromo-7-cyano-2-naphthyl)(difluoro)methyl]phosphonic acid, a potent and orally active small molecule PTP1B inhibitor. Bioorganic & medicinal chemistry letters. 2008 Jun;18(11):3200–3205.
Published In
Bioorganic & medicinal chemistry letters
DOI
EISSN
1464-3405
ISSN
0960-894X
Publication Date
June 2008
Volume
18
Issue
11
Start / End Page
3200 / 3205
Related Subject Headings
- Rats
- Protein Tyrosine Phosphatase, Non-Receptor Type 1
- Organophosphonates
- Neoplasms
- Naphthalenes
- Molecular Structure
- Mice
- Medicinal & Biomolecular Chemistry
- Hydrocarbons, Halogenated
- Haplorhini