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Open Access Articles- Top Results for GSK1360707F

GSK1360707F

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GSK1360707F
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Systematic (IUPAC) name
(1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane
Clinical data
Identifiers
PubChem CID 24802841
Chemical data
Formula C14H17Cl2NO
286.196 g/mol
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GSK1360707F is a new and potent selective triple reuptake inhibitor.[1] structurally related to amitifadine and NS-2359 (GSK-372,475).

Synthesis

File:GSK1360707Fsynthesis.svg
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. ^ PMID 20527970 (PubMed)
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  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. PMID 23685546. doi:10.1124/jpet.112.202895.  edit