SKF-89976A

SKF-89976A
Names
	Other names N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid
Identifiers
CAS Number	85375-85-5;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:91734;
ChEMBL	ChEMBL38686;
ChemSpider	83429;
IUPHAR/BPS	4705;
PubChem CID	92409;
UNII	HKU93AZP6B;
CompTox Dashboard (EPA)	DTXSID101005836 ;
	InChI InChI=1S/C22H25NO2/c24-22(25)20-13-7-15-23(17-20)16-8-14-21(18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-6,9-12,14,20H,7-8,13,15-17H2,(H,24,25) Key: TXQKSMSLZVKQBI-UHFFFAOYSA-N;
	SMILES C1CC(CN(C1)CCC=C(C2=CC=CC=C2)C3=CC=CC=C3)C(=O)O;
Properties
Chemical formula	C22H25NO2
Molar mass	335.447 g·mol−1
Pharmacology
Drug class	GABA reuptake inhibitor; GABA transporter 1 (GAT-1) inhibitor; Anticonvulsant
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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

Synthesis

Synthesis:^[2]^[3] Patent:^[4]^[5]

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).

Related compounds

References

↑ 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

Borden, L. A.; Murali Dhar, T. G.; Smith, K. E.; Weinshank, R. L.; Branchek, T. A.; Gluchowski, C. (1994). "Tiagabine, SK&F 89976-A, CI-966, and NNC-711 are selective for the cloned GABA transporter GAT-1". European Journal of Pharmacology. 269 (2): 219–224. doi:10.1016/0922-4106(94)90089-2. PMID 7851497.

This anticonvulsant-related article is a stub. You can help Wikipedia by adding missing information.

[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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