Inhibitors of Advanced Glycation End Products
a technology of end products and inhibitors, which is applied in the field of advanced lipoxidation endproducts, advanced glycation endproducts, and advanced glycation endproducts, which can solve the problems of no consensus at present on relative importance, and achieve the effects of inhibiting the development of age- and/or ale-associated complications, inhibiting ultrafiltration failure and peritoneal membrane destruction, and improving permeability of the peritoneal membran
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example 1
4-(4,5-Diethyl-1,1-imidazol-2-yl)-5-hydroxymethyl-2-methyl-pyridin-3-ol
[0316]
[0317]Pyridoxal hydrochloride (2.03 g, 10 mmol) was dissolved in MeOH (25 mL) and cooled to 0-5° C. 3,4-Hexanedione (8.4 mL, 70 mmol) was added at 0-5° C. and then aq. ammonium hydroxide solution (25%, 8 mL) keeping the temperature between 5-10° C. The reaction mixture was warmed to rt and stirred over a period of 15 h. The suspension was filtered and the filtrate was evaporated to distill off MeOH. Water (10 mL) was added and extracted with ethyl acetate (4×15 mL). The combined organic layers were washed with water (10 mL), brine (10 mL), dried over Na2SO4 (5 g) and evaporated to dryness. The residue was suspended in ethyl acetate (10 mL) and diethyl ether (20 mL) and stirred for 30 min. The suspension was filtered off, washed with diethyl ether (20 mL) and dried to give the title compound (920 mg) as yellow crystals.
example 2
4-(4,5-Diphenyl-1H-imidazol-2-yl)-5-hydroxymethyl-2-methyl-pyridin-3-ol
[0318]
[0319]Benzil (2.10 g, 10 mmol), ammonium acetate (11.5 g, 150 mmol) were dissolved in DMSO (60 mL) and heated to 100° C. Pyridoxal hydrochloride (4.1 g, 20 mmol) in DMSO (50 mL) was added drop wise and after 100 min stirring at 100° C. the reaction mixture was poured into icewater (300 mL) and aq. ammonium hydroxide solution (50 mL). The precipitate was filtered off, washed with water (100 mL), dissolved in ethyl acetate (150 mL) and extracted with water (2×50 mL). The organic layer was dried over MgSO4 (10 g) and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with toluene / acetone 7 / 3. Fractions containing product were evaporated to a volume of 50 mL and cooled to 0° C. The precipitate was filtered off and dried to give (250 mg) the title compound as a yellow solid.
example 3
4-[4,5-Bis-(4-fluoro-phenyl)-1,1-imidazol-2-yl)-5-hydroxymethyl-2-methyl-pyridin-3-ol
[0320]
[0321]4,4′-Difluorobenzil (2.46 g, 10 mmol), ammonium acetate (11.5 g, 150 mmol) were dissolved in DMSO (60 mL) and heated to 100° C. Pyridoxal hydrochloride (6.1 g, 30 mmol) in DMSO (50 mL) was added drop wise over a period of 40 min. The reaction mixture was cooled to rt and poured into icewater (300 mL) and aq. ammonium hydroxide solution (50 mL). The precipitate was filtered off, washed with water (100 mL), dissolved in ethyl acetate (150 mL) and extracted with water (2×50 mL). The organic layer was dried over MgSO4 (10 g) and evaporated to dryness. The residue was purified by flash chromatography on silica gel eluting with toluene / acetone 7 / 3. Fractions containing product were evaporated to a volume of 50 mL and cooled to 0° C. The precipitate was filtered off and dried to give (250 mg) the title compound as a yellow solid.
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