SKF-89976A

SKF-89976A is an anticonvulsant, acting as a GABA reuptake inhibitor via blockade of GAT-1.[1]

SKF-89976A
Names
Other names
N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid
Identifiers
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).
Infobox references

Synthesis

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

References
  1. 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.
  2. Lscher, W.; SK&F-89976-A. Drugs Fut 1986, 11, 1, 36.
  3. 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.
  4. William E. Bondinell, John J. Lafferty, & Charles L. Zirkle, U.S. patent 4,383,999 (1983 to SmithKline Beecham Corp).
  5. William E. Bondinell, et al. EP0066456 (1985 to SmithKline Beecham Corp).
  6. 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.
  7. Knud Erik Andersen, et al. WO1995018793 (to Novo Nordisk AS).


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