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Gsk1360707f

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Title: Gsk1360707f  
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Subject: Serotonin–norepinephrine–dopamine reuptake inhibitor, Caffeine, Isoethcathinone, TC-2216, DBL-583
Collection: Serotonin-Norepinephrine-Dopamine Reuptake Inhibitors
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Gsk1360707f

GSK1360707F
Systematic (IUPAC) name
(1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane
Clinical data
Legal status
?
Identifiers
ATC code ?
PubChem
Chemical data
Formula C14H17Cl2NO 
Mol. mass 286.196 g/mol
 YesY   

GSK1360707F is a new and potent selective triple reuptake inhibitor.[1] structurally related to amitifadine and NS-2359 (GSK-372,475).

Synthesis

Synthesis of GSK1360707F: WO 2008031772 
  1. BOC Protecting group.
  2. Enolization and trapping with triflate group.
  3. Suzuki reaction
  4. Reduction (only 1 mol eq. LAH because N-BOC can be reduced to N-Me)
  5. Trifluoroacetic acid (TFA) removal of protecting group.
  6. Simmons–Smith reaction cyclopropanation.
  7. Williamson ether synthesis (c.f. NS patents & paxil).

PET

GSK1360707F has recently (2013) been tested on baboons (Papio anubis) & humans for transporter occupancy.[2]

References

  1. ^ Micheli, F.; Cavanni, P.; Andreotti, D.; Arban, R.; Benedetti, R.; Bertani, B.; Bettati, M.; Bettelini, L.; Bonanomi, G.; Braggio, S.; Carletti, R.; Checchia, A.; Corsi, M.; Fazzolari, E.; Fontana, S.; Marchioro, C.; Merlo-Pich, E.; Negri, M.; Oliosi, B.; Ratti, E.; Read, K. D.; Roscic, M.; Sartori, I.; Spada, S.; Tedesco, G.; Tarsi, L.; Terreni, S.; Visentini, F.; Zocchi, A.; Zonzini, L. (2010). "6-(3,4-Dichlorophenyl)-1-[(Methyloxy)methyl]-3-azabicyclo[4.1.0]heptane: A New Potent and Selective Triple Reuptake Inhibitor". Journal of Medicinal Chemistry 53 (13): 4989–5001.  
  2. ^ Comley, R. A.; Salinas, C. A.; Slifstein, M.; Petrone, M.; Marzano, C.; Bennacef, I.; Shotbolt, P.; Van Der Aart, J.; Neve, M.; Iavarone, L.; Gomeni, R.; Laruelle, M.; Gray, F. A.; Gunn, R. N.; Rabiner, E. A. (2013). "Monoamine Transporter Occupancy of a Novel Triple Reuptake Inhibitor in Baboons and Humans Using Positron Emission Tomography". Journal of Pharmacology and Experimental Therapeutics 346 (2): 311–7.  
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