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2 protocols using tetrahydroquinoline

1

Comprehensive Synthesis of Quinoline and Isoquinoline Derivatives

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Chemicals and solvents were used without further purification as they were of the highest commercial grade, unless otherwise stated. 1,2,3,4-Tetrahydroquinoline, 1,2,3,4-Tetrahydroisoquinoline, Tris(2,2-bipyridyl)dichlororuthenium(II)hexahydrate, (Ru(bpy)3Cl2.6H2O), Tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3), 2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene (BINAP), Bromobenzene, 4-Iodoanisole, 4-IodoToluene, 4-Fluroiodobenzene, Methyliodide, Sodium tert-butoxide, Pyridine chloride, Ammonium hydroxide, Magnesium sulfate, Formic acid, triethylamine, Pottasium carbonate, (1Z,5Z)-cycloocta-1,5-diene and all the solvents (Acetonitrile, trideuteroAcetonitrile, Toluene, Dichloromethane, Cyclohexane, Tetrahydrofuran, Ethyl acetate, Ethanol, Chloroform) were purchased from Sigma-Aldrich. Decahydroquinoline and Decahydroisoquinoline were purchased from Ark Pharm, Inc. All the N-derivatives of Tetrahydroquinoline and Tetrahydroisoquinoline were synthesized in-house under N2 environment (see supporting information for synthetic details).
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2

Synthesis and Characterization of Gabazine-Oregon Green

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Drugs R(+)-Etomidate (etomidate) was purchased from Toronto Research Chemicals Inc. (North York, Ontario, Canada) . The salts used in buffers, HEPES, GABA, propofol, DMEM high glucose, fetal bovine serum, and 0.01% poly-L-Lys solution (70-150 kDa) were purchased from Sigma-Aldrich (St. Louis, MO, USA). Pregnenolone sulfate was purchased from Bio-Techne Corp. (Minneapolis, MN, USA) and Sigma-Aldrich. Phenobarbital was obtained from J.T. Baker Chemical Co (Phillipsburg, NJ, USA). Lipofectamine 2000, Opti-MEM, and trypsin-EDTA were obtained from Thermo Fischer Scientific (Waltham, MA, USA). (E)-3-(furan-2-yl)acrylic acid, (E)-3-(2thienyl)acrylic acid, 1-hydroxybenzotriazole hydrate (HOBt), p-toluidine, tetrahydroquinoline, tetrahydroisoquinoline and 1-aminoindoline hydrochloride were obtained from Sigma-Aldrich SRL (Milan, Italy) .
N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC), triethylamine, sodium hydride and iodomethane were purchased from Fluorochem (Glossop, UK).
Gabazine-oregon green (Gzn-OG) was synthesized as described previously (Sakamoto et al., 2019) .
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