Dioxane-modified tetrahydrocarboline-3-formyl-the-hgk, its preparation, antitumor activity and application
A technology of dioxane, -the-his-gly-lys, applied in dioxane-modified tetrahydrocarboline-3-formyl-The-HGK, its preparation, anti-tumor activity and application fields, Addresses issues such as multidrug resistance, troubled cancer care, expensive treatments, and more
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Embodiment 1
[0023] Example 1 Preparation of (3S)-1,1-dimethylol-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1)
[0024] 2 g (7.2 mmol) of L-tryptophan benzyl ester was added to 10 mL of dichloromethane, and the mixture was thoroughly stirred to dissolve. Under ice bath conditions, 1 mL of trifluoroacetic acid was slowly added dropwise to the solution. Then, 0.78 g (8.6 mmol) of 1,3-dihydroxyacetone was added to the solution, and the reaction was carried out at room temperature for 7 hours. TLC showed disappearance of L-tryptophan benzyl ester (dichloromethane / methanol: 30:1). Under ice bath conditions, 50 mL of saturated NaHCO was added to the solution 3 solution, stirred well, and then left a dichloromethane layer, which was then washed with saturated NaHCO 3 The solution (30 mL×3) was washed with saturated NaCl solution (30 mL×3), and the dichloromethane layer was dried with anhydrous sodium sulfate for 12 hours. Filtration and concentration of the filtrate under reduced ...
Embodiment 2
[0025] Example 2 Preparation of 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro-β-carboline-3- Benzyl carboxylate (2) Add 0.2 g (0.55 mmol) of (3S)-1,1-dimethylol-tetrahydro-β-carboline-3-carboxylic acid benzyl ester (1) to 5 mL of anhydrous acetone . In an ice bath, 100 μL of concentrated sulfuric acid was added thereto, followed by stirring at room temperature for 3 hours. TLC showed disappearance of compound 1 (petroleum ether / ethyl acetate, 4:1). in an ice bath with saturated NaHCO 3 The pH value of the reaction solution was adjusted to 7, the obtained solution was concentrated under reduced pressure to remove acetone, the residue was extracted and washed three times with ethyl acetate, and the ethyl acetate layer was washed with saturated NaCl solution until neutral. The ethyl acetate layer was dried over anhydrous sodium sulfate for 12 hours. After filtration, the filtrate was concentrated under reduced pressure to obtain a brownish-yellow solid, which w...
Embodiment 3
[0026] Example 3 Preparation of 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro-β-carboline-3- Carboxylic acid (3)
[0027] To 10 mL of methanol was added 0.20 g (0.5 mmol) of 3S-1-(1,1-dimethyl-1,3-dioxane-6-spiroyl)-1,2,3,4-tetrahydro- Beta-carboline-3-carboxylate benzyl ester (2) and 0.02 g Pd / C. After stirring and passing hydrogen for 12 h, TLC showed disappearance of compound 2 (petroleum ether / ethyl acetate, 4:1). Palladium on carbon (Pd / C) was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was triturated with ether to give 0.14 g (90%) of the title compound as a colorless solid. ESI-MS(m / e): 317[M+H] + .
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