Dioxane modified tetrahydrocarboline-3-formyl-The-EDG, and preparation, anti-metastasis activity and application of dioxane modified tetrahydrocarboline-3-formyl-The-EDG
A dioxane, -the-glu-asp-gly technology, applied in the preparation methods of peptides, organic active ingredients, medical preparations of non-active ingredients, etc., can solve the problems of multidrug resistance and cancer treatment. Difficulties, Expensive Treatment Prices, etc.
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Embodiment 1
[0022] Example 1 Preparation (3S) -1, 1-dihydroxymethyl-tetrahydro-β-kethane-3-carboxylate (1)
[0023] 2 g (7.2 mmol) of L-tryptophan benzyl ester was added to 10 ml of dichloromethane, and thoroughly stirred it. Under ice bath, 1 ml of trifluoroacetic acid was slowly added dropwise. Then, 0.78 g (8.6 mmol) 1,3-dihydroxyacetone was added to the solution, and the room temperature was reacted for 7 hours. TLC showed L-tryptophan benzyl disappearance (dichloromethane / methanol: 30: 1). Under ice bath, 50ml saturated NaHCO is added to the solution 3 Solution, stir well, then leave a dichloromethane layer, then use saturated NaHCO 3 Solution (30 mL × 3) washing, then washed with saturated NaCl (30 ml × 3), dried over anhydrous sodium sulfate for 12 hours with anhydrous sodium sulfate. Filtration, the filtrate was concentrated to give 2.03 g (77%) title compound to be a yellow powder. ESI-MS (M / E): 367 [M + H] + .
Embodiment 2
[0024] Example 2 Preparation 3S-1- (1,1-dimethyl-1,3-dioxane-6-) -1,2,3,4-tetrahydro-β-β-β-β-β-3- Benzyl carboxylate (2)
[0025] 0.2 g (0.55 mmol) (3S) -1,1-dihydroxymethyl-tetrahydro-β-p-3-carboxylate (1) was added to 5 ml anhydrous acetone. Under ice bath, 100 μl of concentrated sulfuric acid was added, and then stirred at room temperature for 3 hours. The TLC showed the compound 1 disappeared (petroleum ether / ethyl acetate, 4: 1). Under ice bath, with saturated NAHCO 3 The solution regulates the reaction liquid pH of 7, and the resulting solution was concentrated under reduced pressure, and the residue was then raised by ethyl acetate, and the ethyl acetate layer was washed to neutral with a saturated NaCl solution. Ethyl acetate layer was dried over anhydrous sodium sulfate for 12 hours. Filtration, the filtrate was concentrated under reduced pressure, separated from the column chromatography (EtOAc EtOAc) EtOAc (35.8%) ESI-MS (M / E): 407 [M + H] + .
Embodiment 3
[0026] Example 3 Preparation 3S-1- (1, 1-dimethyl-1,3-dioxane-6-) -1,2,3,4-tetrahydro-β-β-β-β-3- Carboxylic acid (3)
[0027] 0.20 g (0.5 mmol) of 3S-1- (1,1-dimethyl-1,3-dioxane-6-spiro) -1, 2, 3, 4-tetrahydrogen - β-p-3-carboxylate (2) and 0.02 g of Pd / c. The mixture was stirred and passed by hydrogen, TLC showed compound 2 disappeared (petroleum ether / ethyl acetate, 4: 1). Palladium carbon (PD / C) was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was washed with diethyl ether to give 0.14 g (90%) title compound for colorless solids. ESI-MS (M / E): 317 [M + H] + .
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