GSK1360707F

From Wikipedia, the free encyclopedia
Jump to: navigation, search
GSK1360707F
GSK1360707F structure.png
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 CID 24802841
Chemical data
Formula C14H17Cl2NO 
Mol. mass 286.196 g/mol
 YesY (what is this?)  (verify)

GSK1360707F is a new and potent selective triple reuptake inhibitor.[1]

This research chemical is still relatively new so no details are available for it yet.

It sort of has certain similarities between Amitifadine and NS-2359 (GSK-372,475).

Synthesis[edit]

This is the basic synthesis of GSK1360707F.
  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 (i think other schemes too for last-step if look at NS patents & possibly paxil).

Advanced Synthesis[edit]

[2][3][4]

Baboons[edit]

GSK1360707F has recently (2013) been tested on baboons (Papio anubis) for transporter occupancy.[5]

See also[edit]

References[edit]

  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. doi:10.1021/jm100481d. PMID 20527970.  edit
  2. ^ Elitzin, V. I.; Harvey, K. A.; Kim, H.; Salmons, M.; Sharp, M. J.; Tabet, E. A.; Toczko, M. A. (2010). "Development of a New Synthesis for the Large-Scale Preparation of Triple Reuptake Inhibitor (−)-GSK1360707". Organic Process Research & Development 14 (4): 912. doi:10.1021/op100139f.  edit
  3. ^ doi:10.1016/j.tetlet.2011.05.005
    This citation will be automatically completed in the next few minutes. You can jump the queue or expand by hand
  4. ^ Deschamps, N. M.; Elitzin, V. I.; Liu, B.; Mitchell, M. B.; Sharp, M. J.; Tabet, E. A. (2010). "An Enyne Cycloisomerization Approach to the Triple Reuptake Inhibitor GSK1360707F". The Journal of Organic Chemistry 76 (2): 712–715. doi:10.1021/jo102098y. PMID 21174473.  edit
  5. ^ 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. doi:10.1124/jpet.112.202895. PMID 23685546.  edit