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Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor
Open accessAbstract
Previously it was found that a conformationally rigid analogue (2) of the epilepsy drug vigabatrin (1) did not inactivate gamma-aminobutyric acid aminotransferase (GABA-AT). A cyclic compound with an exocyclic double bond (6) was synthesized and was found to inactivate GABA-AT, but only in the absence of 2-mercaptoethanol. The corresponding difluoro-substituted analogue (14) was synthesized and was shown to be a very potent time-dependent inhibitor, even in the presence of 2-mercaptoethanol.
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Cited by
Metabolic and Pharmaceutical Aspects of Fluorinated Compounds
Johnson, B. M., Shu, Y.-Z., Zhuo, X., & Meanwell, N. A. (2020) · Journal of Medicinal Chemistry · doi:10.1021/acs.jmedchem.9b01877 · Cited by 719
Direct electrochemical defluorinative carboxylation of α-CF 3 alkenes with carbon dioxide
Gao, X.-T., Zhang, Z., Wang, X., Tian, J.-S., Xie, S.-L., Zhou, F., & Zhou, J. (2020) · Chemical Science · doi:10.1039/d0sc04091f · Cited by 142
Metadata
- Authors
- Pan, Y., Qiu, J., & Silverman, R. B.
- Venue
- Journal of Medicinal Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-11-11
- Volume
- 46
- Issue
- 25
- Pages
- 5292-5293
- ISSN
- 0022-2623 (ISSN-L)
- 1520-4804
- OpenAlex
- W2023363265
- Cited by
- 228
- References
- 0
- FWCI
- 2.67
- Type
- journal article
- Language
- en
- Open access
- green
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- CoChat. (2026). Citation check: Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor. https://app.cochat.ai/papers/10.1021/jm034162s
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- Pan, Y., Qiu, J., & Silverman, R. B. (2003). Design, Synthesis, and Biological Activity of a Difluoro-Substituted, Conformationally Rigid Vigabatrin Analogue as a Potent γ-Aminobutyric Acid Aminotransferase Inhibitor. Journal of Medicinal Chemistry. https://doi.org/10.1021/jm034162s
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