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SKF-89976A

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SKF-89976A
Names

Other names N-(4,4-diphenyl-3-butenyl)-3-piperidinecarboxylic acid
Identifiers
CAS Number	85375-85-5
IUPHAR/BPS	4705
PubChem CID	92409
CompTox Dashboard(EPA)	DTXSID101005836
Properties
Chemical formula	C₂₂H₂₅NO₂
Molar mass	335.447 g·mol⁻¹
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

SKF-89976A is ananticonvulsant, acting as aGABA reuptake inhibitor via blockade ofGAT-1.^[1]

Synthesis

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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).

References

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^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

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Tiagabine, SK&F 89976-A, CI-966, and NNC-711 are selective for the cloned GABA transporter GAT-1

GABATooltip γ-Aminobutyric acidmetabolism andtransport modulators

Transporter

GATTooltip GABA transporter	Inhibitors:4-Aminovaleric acid β-Alanine Arecaidine CI-966 DABA Deramciclane (EGIS-3886, EGYT-3886) EF-1502 Gabaculine Guvacine Ibotenic acid Muscimol Nipecotic acid NNC 05-2090 NO-711 Riluzole SKF-89976A SNAP-5114 TACA Tiagabine
VIAATTooltip Vesicular inhibitory amino acid transporter	Inhibitors:β-Alanine Bafilomycin A1 Chicago sky blue 6B Evans blue GABA Glycine N-Butyric acid Nigericin Nipecotic acid Valinomycin Vigabatrin

Enzyme

GADTooltip Glutamate decarboxylase	Inhibitors:3-Mercaptopropionic acid AAOA L-Allylglycine Semicarbazide Activators:3-Methyl-GABA
GABA-TTooltip γ-Aminobutyrate aminotransferase	Inhibitors:3-Hydrazinopropionic acid DABA γ-Acetylenic-GABA AOAA EOS Gabaculine Isoniazid L-Cycloserine Phenelzine PEH Rosmarinic acid (lemon balm) Sodium valproate Valnoctamide Valproate pivoxil Valproate semisodium (divalproex sodium) Valproic acid Valpromide Vigabatrin Activators:3-Methyl-GABA