Chemistry:GSK1360707F

GSK1360707F
Identifiers
	IUPAC name (1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane;
CAS Number	1013098-04-8 ;
PubChem CID	24802841;
ChemSpider	32739425;
UNII	9DE44WJ46X;
Chemical and physical data
Formula	C14H17Cl2NO
Molar mass	286.20 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC[C@@]12C[C@@]1(CCNC2)c3ccc(c(c3)Cl)Cl;
	InChI InChI=1S/C14H17Cl2NO/c1-18-9-13-7-14(13,4-5-17-8-13)10-2-3-11(15)12(16)6-10/h2-3,6,17H,4-5,7-9H2,1H3/t13-,14-/m0/s1; Key:ICXJGCSEMJXNQF-KBPBESRZSA-N;
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Short description: Chemical compound

GSK1360707F is a potent and selective triple reuptake inhibitor.^[1] It is chemically related to amitifadine and NS-2359 (GSK-372,475). Until recently,^[when?] it was under development for the treatment of major depressive disorder; its development was put on hold for strategic reasons.^{[citation needed]}

Synthesis

Synthesis of GSK1360707F^[2]

BOC Protecting group.
Enolization and trapping with triflate group (cf Comins' reagent).
Suzuki reaction
Reduction (only 1 mol eq. LAH because N-BOC can be reduced to N-Me)
Trifluoroacetic acid (TFA) removal of protecting group.
Simmons–Smith reaction cyclopropanation.
Williamson ether synthesis (c.f. NS patents & paxil).

Transporter occupancy

GSK1360707F has recently (2013) been tested on baboons (Papio anubis) & humans for transporter occupancy using PET.^[3]

References

↑ "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. July 2010. doi:10.1021/jm100481d. PMID 20527970.
↑ Bertani, Barbara; Romano Di Fabio & Fabrizio Micheli et al., "Azabicyclic compounds as inhibitors of monoamines reuptake", WO patent 2008031772, published 2008-03-20
↑ "Monoamine transporter occupancy of a novel triple reuptake inhibitor in baboons and humans using positron emission tomography". The Journal of Pharmacology and Experimental Therapeutics 346 (2): 311–7. August 2013. doi:10.1124/jpet.112.202895. PMID 23685546.

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[1] "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. July 2010. doi:10.1021/jm100481d. PMID 20527970.

[2] Bertani, Barbara; Romano Di Fabio & Fabrizio Micheli et al., "Azabicyclic compounds as inhibitors of monoamines reuptake", WO patent 2008031772, published 2008-03-20

[3] "Monoamine transporter occupancy of a novel triple reuptake inhibitor in baboons and humans using positron emission tomography". The Journal of Pharmacology and Experimental Therapeutics 346 (2): 311–7. August 2013. doi:10.1124/jpet.112.202895. PMID 23685546.

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[2]

[3]

v t e Adrenergic receptor modulators
α₁	Agonists: 6-FNE Amidephrine Anisodine Buspirone Cirazoline Corbadrine Desglymidodrine Dexisometheptene Dipivefrine Dopamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etilefrine Etilevodopa Ethylnorepinephrine Indanidine Isometheptene L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Melevodopa Metaraminol Methoxamine Methyldopa Midodrine Naphazoline Norepinephrine Octopamine (drug) Oxymetazoline Phenylephrine Phenylpropanolamine Pseudoephedrine Synephrine Tetryzoline Tiamenidine XP21279 Xylometazoline Antagonists: Abanoquil Adimolol Ajmalicine Alfuzosin Amosulalol Anisodamine Arotinolol Atiprosin Atypical antipsychotics (e.g., brexpiprazole, clozapine,Chemistry:Olanzapine
α₂	Agonists: (R)-3-Nitrobiphenyline 4-NEMD 6-FNE Amitraz Apraclonidine Brimonidine Cannabivarin Clonidine Corbadrine Detomidine Dexmedetomidine Dihydroergotamine Dipivefrine Dopamine Droxidopa (L-DOPS) Etilevodopa Ephedrine Ergotamine Epinephrine Etilefrine Ethylnorepinephrine Guanabenz Guanfacine Guanoxabenz L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Lofexidine Medetomidine Melevodopa Methyldopa Mivazerol Naphazoline Norepinephrine Oxymetazoline Phenylpropanolamine Piperoxan Pseudoephedrine Rezatomidine Rilmenidine Romifidine Talipexole Tasipimidine Tetrahydrozoline Tiamenidine Tizanidine Tolonidine Urapidil Vatinoxan XP21279 Xylazine Xylometazoline Antagonists: 1-PP Adimolol Amesergide Aptazapine Atipamezole Atypical antipsychotics (e.g., asenapine, Chemistry:Brexpiprazole
β	Agonists: Abediterol Alifedrine Amibegron Arbutamine Arformoterol Arotinolol BAAM Bambuterol Befunolol Bitolterol Broxaterol Buphenine Carbuterol Carmoterol Cimaterol Clenbuterol Colterol Corbadrine Denopamine Dipivefrine Dobutamine Dopamine Dopexamine Droxidopa (L-DOPS) Ephedrine Epinephrine Etafedrine Etilefrine Etilevodopa Ethylnorepinephrine Fenoterol Formoterol Hexoprenaline Higenamine Indacaterol Isoetarine Isoprenaline Isoxsuprine L-DOPA (levodopa) L-Phenylalanine L-Tyrosine Levosalbutamol Mabuterol Melevodopa Methoxyphenamine Methyldopa Mirabegron Norepinephrine Orciprenaline Oxyfedrine PF-610355 Phenylpropanolamine Pirbuterol Prenalterol Ractopamine Procaterol Pseudoephedrine Reproterol Rimiterol Ritodrine Salbutamol Salmeterol Solabegron Terbutaline Tretoquinol Tulobuterol Vilanterol Xamoterol XP21279 Zilpaterol Zinterol Antagonists: Acebutolol Adaprolol Adimolol Afurolol Alprenolol Alprenoxime Amosulalol Ancarolol Arnolol Arotinolol Atenolol Befunolol Betaxolol Bevantolol Bisoprolol Bopindolol Bornaprolol Brefonalol Bucindolol Bucumolol Bufetolol Bufuralol Bunitrolol Bunolol Bupranolol Butaxamine Butidrine Butofilolol Capsinolol Carazolol Carpindolol Carteolol Carvedilol Celiprolol Cetamolol Cicloprolol Cinamolol Cloranolol Cyanopindolol Dalbraminol Dexpropranolol Diacetolol Dichloroisoprenaline Dihydroalprenolol Dilevalol Diprafenone Draquinolol Ecastolol Epanolol Ericolol Ersentilide Esatenolol Esprolol Eugenodilol Exaprolol Falintolol Flestolol Flusoxolol Hydroxycarteolol Hydroxytertatolol ICI-118,551 Idropranolol Indenolol Indopanolol Iodocyanopindolol Iprocrolol Isoxaprolol Isamoltane Labetalol Landiolol Levobetaxolol Levobunolol Levomoprolol Medroxalol Mepindolol Metipranolol Metoprolol Moprolol Nadolol Nadoxolol Nebivolol Nifenalol Nipradilol Oxprenolol Pacrinolol Pafenolol Pamatolol Pargolol Penbutolol Pindolol Practolol Primidolol Procinolol Pronethalol Propafenone Propranolol Ridazolol Ronactolol Soquinolol Sotalol Spirendolol SR 59230A Sulfinalol Talinolol Tazolol Tertatolol Tienoxolol Tilisolol Timolol Tiprenolol Tolamolol Toliprolol Xibenolol Xipranolol

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Identifiers

IUPAC name (1R,6S)-1-(3,4-Dichlorophenyl)-6-(methoxymethyl)-4-azabicyclo[4.1.0]heptane
CAS Number	1013098-04-8^Y
PubChem CID	24802841
ChemSpider	32739425
UNII	9DE44WJ46X
Chemical and physical data
Formula	C₁₄H₁₇Cl₂NO
Molar mass	286.20 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC[C@@]12C[C@@]1(CCNC2)c3ccc(c(c3)Cl)Cl
InChI InChI=1S/C14H17Cl2NO/c1-18-9-13-7-14(13,4-5-17-8-13)10-2-3-11(15)12(16)6-10/h2-3,6,17H,4-5,7-9H2,1H3/t13-,14-/m0/s1 Key:ICXJGCSEMJXNQF-KBPBESRZSA-N
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Chemistry:GSK1360707F

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