Chemokine receptor antagonists and use thereof
a technology of chemokine receptor and antagonist, which is applied in the field of chemokine receptor antagonists, can solve the problems of malignant tumors, easy complexity of various opportunistic infections such as carinii pneumonia, and gradual deterioration of immune functions, and achieve the effect of being used as a preventive and/or therapeutic agen
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example 1
1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole
[0612]Under an argon atmosphere, a dimethylformamide (500 mL) suspension of sodium hydride (60%, 18.9 g) was ice-cooled and then imidazole (30.9 g) was added so as to prevent an inner temperature from rising to 5° C. or higher. The reaction solution was stirred at 0° C. for 45 minutes. To the reaction solution, 2-(trimethylsilyl)ethoxymethyl chloride (72.4 g) was added dropwise. The reaction solution was stirred at room temperature for 14 hours. To the reaction solution, ice water (200 mL) was added. The aqueous layer was extracted twice with a solution (n-hexane:ethyl acetate=1:1 (200 mL)). The combined organic layer was washed with saturated sodium chloride solution and then dried over anhydrous magnesium sulfate. After removing anhydrous magnesium sulfate by filtration, the filtrate was concentrated to obtain the title compound (116 g) having the following physical properties.
[0613]TLC: Rf 0.50 (ethyl acetate:methanol=9:1);
[0614]NM...
example 2
(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methanol
[0615]To an anhydrous tetrahydrofuran (1,000 mL) solution of compound (115 g) produced in Example 1, a tetrahydrofuran solution (260 mL) of 2N lithium diisopropylamide was added at −78° C. under an argon atmosphere. The reaction solution was stirred at −78° C. for 2 hours. To this solution, dimethylformamide (100 mL) was added. The reaction solution was stirred at 0° C. for 30 minutes. To the reaction solution, water (200 mL) was added. The reaction solution was concentrated under reduced pressure. The aqueous layer was extracted three times with ethyl acetate (200 mL). The combined organic layer was washed in turn with water (100 mL) and saturated sodium chloride solution (100 mL), and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1→2:1) to obtain the...
example 3
2-(chloromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazole Hydrochloride
[0618]To a dichloromethane (30 mL) solution of the compound (2.44 g) produced in Example 2, thionyl chloride (1.85 mL) was added at 0° C. under an argon atmosphere. The reaction solution was stirred at room temperature for 30 minutes. To the reaction solution, a solution (n-hexane:ethyl acetate=1:1 (100 mL)) was added. The precipitated solid was collected by filtration. The solid was dried under reduced pressure to obtain the title compound (2.42 g) having the following physical properties.
[0619]TLC: Rf 0.71 (ethyl acetate:methanol:28% aqueous ammonia=90:10:1);
[0620]NMR (CDCl3): δ 0.00-0.08 (m, 9H), 0.98 (dd, J=8.4, 7.8 Hz, 2H), 3.62 (t, J=8.4 Hz, 2H), 5.20 (s, 2H), 5.57 (s, 2H), 7.29 (d, J=1.8 Hz, 1H), 7.38 (d, J=1.8 Hz, 1H).
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