Inhibitors of cognitive decline
An alkyl, pharmaceutical technology for compounds derived from plant extracts capable of addressing chemical and biological instability
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[0249]The preparation of the compounds of the present invention may involve the protection and deprotection of various chemical groups. The need for protection and deprotection, and the selection of suitable protecting groups, can be readily determined by those skilled in the art. The chemistry of protecting groups can be found, for example, in T.W. Greene and P.G.M. Wuts, Protective Groups in Organic Synthesis, 3rd Edition, Wiley & Sons, Inc., New York (1999), which is incorporated herein by reference in its entirety .
[0250] Reactions can be monitored according to any suitable method known in the art. For example, product formation can be detected by spectroscopic means such as NMR spectroscopy (eg 1 H or 13 C), infrared spectroscopy, spectrophotometry (eg, UV-visible), mass spectroscopy, or monitoring by chromatographic methods such as high performance liquid chromatography (HPLC) or thin layer chromatography (TLC).
[0251] Compounds of embodiments of the present inv...
Embodiment 1
[0341] A. Extraction of conditioned ginger oil: reaction of ginger oil with 4-chlorobenzylamine, followed by reduction with sodium borohydride in methanol, and fractionation using column chromatography
[0342] Ginger oil (10 g) was dissolved in toluene (250 mL) and 4-chlorobenzylamine (3.4 g) was added. The mixture was kept under a nitrogen atmosphere and heated at reflux for 16 hours with removal of water through a Dean-Stark distillation apparatus. At this point, the Dean-Stark trap was removed, and the reaction mixture was cooled to 0°C on an ice bath. With vigorous stirring, a solution of sodium borohydride (10 g) in methanol (100 mL) was added portionwise over 30 minutes. When the addition was complete, the mixture was heated at reflux for 16 hours. At this point, the reaction mixture was cooled to room temperature and poured into saturated aqueous sodium bicarbonate (300 mL). The resulting mixture was concentrated by rotary evaporation, and the aqueous residue was pa...
Embodiment 2
[0363] A. Extraction of conditioned ginger oil: reaction of ginger oil with 4-trifluoromethylbenzylamine, followed by reduction with sodium borohydride in methanol, and fractionation using column chromatography
[0364] Ginger oil (10 g) was dissolved in toluene (250 mL) and 4-trifluoromethylbenzylamine (3.5 g) was added. The mixture was kept under a nitrogen atmosphere and heated at reflux for 16 hours with removal of water through a Dean-Stark distillation apparatus. At this point, the Dean-Stark trap was removed, and the reaction mixture was cooled to 0°C on an ice bath. With vigorous stirring, a solution of sodium borohydride (10 g) in methanol (100 mL) was added portionwise over 30 minutes. When the addition was complete, the mixture was heated at reflux for 16 hours. At this point, the reaction mixture was cooled to room temperature and poured into saturated aqueous sodium bicarbonate (300 mL). The resulting mixture was concentrated by rotary evaporation, and the aque...
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