Prodrug of galactoside inhibitors of galectins
A kind of galactopyranosyl, prodrug technology, applied in the field of new prodrug compounds
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example 1
[0403] 5-bromo-3-deoxy-3-yl-3- [4- (3,4,5-trifluorophenyl) -1H-1,2,3- triazol-1-yl] -6-O - 1-thio phosphate -α-D- galactopyranoside
[0404]
[0405] 5-bromo-pyridin-3-yl 6-O- tert-butyldimethylsilyl-3-deoxy-3- [4- (3,4,5-trifluorophenyl) -1H-1,2,3 - triazol-1-yl] -1-thio -α-D- galactopyranoside
[0406]
[0407] 5-bromo-3-deoxy-3-yl-3- [4- (3,4,5-trifluorophenyl) -1H-1,2,3- triazol-1-yl] -1 thio -α-D- galactopyranoside (200mg, 0.375mmol) in DMF (5mL) was added imidazoline (43.9mg, 0.563mmol) and TBS-Cl (84.4mg, 0.563mmol). In n 2 The reaction was stirred under an atmosphere at room temperature for 6 hours. Water was added (20mL) and DCM (20mL). The aqueous phase was extracted, washed combined organic layers washed with water (20mL) and brine (20mL), and dried over anhydrous sodium sulfate with DCM (15mL × 2). The solvent was removed in vacuo to give the title compound, which was used without further purification in the next step. [C25H30BrF3N4O4SSi] + [M + h] + The m / z calc...
example 2
[0426]5-bromopyridine-3-yl-3-deoxidation-3- [4- (3,4,5-trifluorophenyl) -1H-1, 2, 3-triazole-1-yl] -2 - Phosphate-1-thio-α-D-pyride galactoside
[0427]
[0428] 5-bromopyrid-3-yl 4,6-O-bubbazole-3-deoxidation-3- [4- (3,4,5-trifluorophenyl) -1H-1, 2, 3-triazole -1-yl] -2-O-phosphate-1-thioside-α-D-pyrid
[0429]
[0430] In n 2 Atmosphere 0 ° C, 5-bromipate-3-yl 4,6-O-bubbazyl-3-deoxidation-3- [4- (3,4,5-trifluorophenyl) -1H-1 2,3-triazole-1-yl] -1-thio-α-D-pyranium galactoside (200 mg, 0.322 mmol) and DMAP (78.6 ml, 0.644 mmol) DCM (15.00 mL) solution Add DIEA (1.38ml, 8.05mol), then add POCL drop 3 (0.147ml, 1.61 mmol). When TLC showed no residual starting material, the vacuum was removed at room temperature, and ammonium hydroxide (15 ml) was added, and the white solid was precipitated, and it was collected by filtration without further purification. Used in the next step.
[0431] [C26H21BRF3N407PS] - [M + h] - M / Z calculated value: 699,701; measured value: 699, 701.
[...
example 3
[0437] 3,4-dichlorophenyl 3-deoxidation-3- [4- (3,4,5-trifluorophenyl) -1H-1, 2, 3-triazole-1-yl] -2-O- Phosphate-1-thio-α-D-pyrid gylactide
[0438]
[0439] 3,4-dichlorophenyl 4,6-O-benzo-3-deoxidation-3- [4- (3,4,5-trifluorophenyl) -1H-1, 2, 3-triazole -1-yl] -1-thio-α-D-gyramide galactoside
[0440]
[0441] To 3,4-dichlorophenyl-4,6-O-BB-3-deoxidation-3- [4- (3,4,5-trifluorophenyl) -1H-1, 2, 3- Avanthene-1-yl] -1-thio-[alpha-D-gyramol) anhydrous MECN (24 ml) solution is added to anhydrous MECN (1 mL) in anhydrous MECN (1 mL). OME) 2 (0.87 mL, 5.791 mmol) and camphor (30 mg, 0.116 mmol). This transparent yellow mixture is stirred at room temperature. After 20 minutes, the reaction mixture became a cloudy white precipitate. After 2 hours, the solvent was evaporated and the reaction was stopped. The crude reactants were dissolved in EtOH (180 mL) under heating conditions and were allowed to crystallize at room temperature for 36 hours. The formed crystals were filtered and d...
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