Opsin-Binding Ligands, Compositions and Methods of Use
a technology of opsin and ligands, applied in the field of opsin-binding ligands, can solve the problems of ophthalmic, opsin can exhibit improper folding, and affect the visual perception of the animal so affected, and achieve the effects of reducing the stress on the photoreceptor cell, promoting the appropriate intracellular processing and transport, and reducing the viability of the photoreceptor cell
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example 1a
romethyl)-N-((2,6,6-trimethylcyclohex-1-enyl)methyl)aniline
[0420]To a stirred solution of 2,6,6-trimethylcyclohex-1-enecarbaldehyde (152 mg, 1.0 mmol) in methanol (3 mL) was added 3-(trifluoromethyl)aniline (161 mg, 1.0 mmol). To the stirred mixture was added acetic acid (0.1 mL) followed by sodium cyanborohydride (188 mg, 3.0 mmol). The reaction was stirred at room temperature for 3 hours and then the reaction was quenched by addition of saturated aqueous ammonium chloride (5 mL). The methanol was evaporated under reduced pressure and the residue was diluted with ethyl acetate (40 mL). The organic phase was washed with water (30 mL×2) and brine (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=100 / 1) to afford the title compound as a colorless oil (200 mg, Yield: 67%). Rf=0.8 (30:1 petroleum ether / ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 7.25 (t, ...
example 1
oromethyl)-N-((2,6,6-trimethylcyclohex-1-enyl)methyl)aniline hydrochloride
[0421]A solution of the product of Example 1a (61 mg, 0.21 mmol) in 4N hydrochloric acid in methanol (5 mL) was stirred at room temperature overnight. The mixture was concentrated to give white solid which was washed by acetone and dried under vacuo to afford the title compound as a white solid (56 mg, Yield: 80%). Mp=123-124.1° C.; 1H NMR (400 MHz, CDCl3) b 7.75 (d, J=8.0 Hz, 1H), 7.72 (s, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.43 (t, J=7.6 Hz, 1H), 4.98 (br, 1H), 3.90 (s, 2H), 1.97 (t, J=6.2 Hz, 2H), 1.58-1.53 (m, 5H), 1.43-1.41 (m, 2H), 0.96 (s, 6H) ppm; Mass spectrum (ESI+ve) m / z 298 (M+H+).
example 2
N-((2,6,6-trimethylcyclohex-1-enyl)methyl)aniline
[0422]To a stirred solution of 2,6,6-trimethylcyclohex-1-enecarbaldehyde (152 mg, 1.0 mmol) in methanol (3 mL) was added m-toluidine (107 mg, 1.0 mmol), acetic acid (0.1 mL) followed by sodium cyanoborhydride (187 mg, 3.0 mmol). The reaction was stirred at room temperature for 1 hour and then was quenched by addition of saturated aqueous ammonium chloride (5 mL). The methanol was was evaporated under reduced pressure and the residue was diluted with ethyl acetate (40 mL). The organic phase was washed with water (30 mL×2) and brine (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: petroleum ether / ethyl acetate=100 / 1) to afford the title compound as a colorless oil (185 mg, Yield: 76%). Rf=0.7 (20:1 petroleum ether / ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 7.09-7.05 (m, 1H), 6.50 (d, J=7.2 Hz, 1H), 6.42 (s, 1H), 6.41 (d, J=7.2 Hz, 1...
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