SKF-89976A
Appearance
![]() | |
Names | |
---|---|
Other names
N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid
| |
Identifiers | |
PubChem CID
|
|
CompTox Dashboard (EPA)
|
|
Properties | |
C22H25NO2 | |
Molar mass | 335.447 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
SKF-89976A is an anticonvulsant, acting as a GABA reuptake inhibitor via blockade of GAT-1.[1]
Synthesis
[edit]![](http://178.128.105.246/content-http-upload.wikimedia.org/wikipedia/commons/thumb/1/18/SKF-89976A_synthesis.svg/500px-SKF-89976A_synthesis.svg.png)
Ex 1: Finkelstein Sn2 alkylation between 1,1-Diphenyl-4-bromobutene [6078-95-1] (1) & Ethyl nipecotate [5006-62-2] (2) gives [89203-62-3] (3). Optional saponification of the ester group gives the title amino-acid compound (4).
See also
[edit]![](http://178.128.105.246/content-http-upload.wikimedia.org/wikipedia/commons/thumb/b/b3/NNC-47-0011.svg/150px-NNC-47-0011.svg.png)
References
[edit]- ^ Moldavan, Michael; Cravetchi, Olga; Allen, Charles N. (2017-12-01). "GABA transporters regulate tonic and synaptic GABAA receptor-mediated currents in the suprachiasmatic nucleus neurons". Journal of Neurophysiology. 118 (6): 3092–3106. doi:10.1152/jn.00194.2017. ISSN 1522-1598. PMC 5814714. PMID 28855287.
- ^ Lscher, W.; SK&F-89976-A. Drugs Fut 1986, 11, 1, 36.
- ^ Ali, Fadia E.; Bondinell, William E.; Dandridge, Penelope A.; Frazee, James S.; Garvey, Eleanor; Girard, Gerald R.; Kaiser, Carl; Ku, Thomas W.; Lafferty, John J.; Moonsammy, George I.; Oh, Hye-Ja; Rush, Julia A.; Setler, Paulette E.; Stringer, Orum D.; Venslavsky, Joseph W.; Volpe, Beth W.; Yunger, Libby M.; Zirkle, Charles L. (1985). "Orally Active and Potent Inhibitors of γ-Aminobutyric Acid Uptake". Journal of Medicinal Chemistry. 28 (5): 653–660. doi:10.1021/jm50001a020.
- ^ William E. Bondinell, John J. Lafferty, & Charles L. Zirkle, U.S. patent 4,383,999 (1983 to SmithKline Beecham Corp).
- ^ William E. Bondinell, et al. EP0066456 (1985 to SmithKline Beecham Corp).
- ^ Cao, R., Cao, Y., Dissing, S., Hansen, A. J., Kristjansen, P. E. G., Olsen, U. B. (September 2003). "579 Significant tumor growth inhibition of glioblastoma xenografts by NNC 47-0011 — a low molecular weight tricyclic tyrosine kinase modulator with anti-angiogenic activity". European Journal of Cancer Supplements. 1 (5): S175. doi:10.1016/S1359-6349(03)90611-2.
- ^ Knud Erik Andersen, et al. WO1995018793 (to Novo Nordisk AS).
External links
[edit]