A crocetin derivative gx-d, its preparation method, and its application in preventing or treating cardiovascular and cerebrovascular diseases
A cardiovascular and cerebrovascular disease, GX-D technology, applied in cardiovascular system diseases, drug combination, organic chemistry, etc., can solve the problem of poor fat solubility and water solubility of crocetin, clinical application limitations, high drug concentration and dosage To prevent or treat cardiovascular and cerebrovascular diseases, overcome low bioavailability, and improve bioavailability
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Embodiment 1
[0036] Embodiment 1 prepares crocetin derivative GX-D
[0037]
[0038] Take GX-1 (purchased from Sigma Company) (0.5mmol, 164mg), EDCI (1.25mmol, 239mg), HOBt (1.25mmol, 169mg) in a 100ml reaction bottle. In an ice bath, add Et 3 N (1.25mmol, 172μl) and CH 2 Cl 2 20ml, finally added piperidine (1.0mmol), reacted at 0°C for 4h, then reacted overnight at room temperature. Use TLC and LC-MS to detect whether the product is generated, and stop the reaction after confirming that the reaction is complete. The reaction solution was filtered, the solvent was removed in vacuo, 10ml of EA was added to dissolve, and 2% HCl, 5% NaHCO 3 , H 2 O each 10ml was washed 3 times, and finally the solvent was removed in vacuo to obtain the crude product. The obtained crude product GX-D is separated with a silica gel column, first two column volumes of CHCl 3 Carry out elution, then increase the eluent polarity CHCl 3 :CH 3 OH=10:1 for elution. Finally, the product GX-D was obtained, ...
Embodiment 2
[0039] Embodiment 2: Preparation of crocetin derivative GX-M:
[0040]
[0041] Separately take crocetin GX-1 (purchased from Sigma) (0.5mmol, 164mg), EDCI (1.25mmol, 239mg), HOBt (1.25mmol, 169mg) in 25ml reaction vials. Under ice bath condition, add Et3N (2.5mmol, 350μl) and CH 2 Cl 2 20ml, finally added 4-fluorobenzylamine (1.1mmol, 125μl), reacted at 0°C for 4h, then reacted overnight at room temperature. Use TCL and LC-MS to detect whether the product is generated, and stop the reaction after confirming that the reaction is complete. The reaction solution was filtered, the solvent was removed in vacuo, 10ml of EA was added to dissolve, and then washed three times with 2% HCl, 5% NaHCO3, 10ml of H2O respectively, and finally the solvent EA was removed in vacuo to obtain the crude product. The resulting crude product was separated on a silica gel column, eluting with three column volumes of CHCl3. Obtain the product GX-M crude product, then again silica gel column se...
Embodiment 3
[0042] Embodiment 3: Preparation of crocetin derivative GX-N:
[0043]
[0044] Separately take crocetin GX-1 (purchased from Sigma) (0.5mmol, 164mg), EDCI (1.25mmol, 239mg), HOBt (1.25mmol, 169mg) in 25ml reaction vials. Under ice bath condition, add Et3N (2.5mmol, 350μl) and CH2 Cl 2 20ml, finally added 3,5-difluorobenzylamine (1.1mmol, 130μl), reacted at 0°C for 4h, then reacted overnight at room temperature. Use TCL and LC-MS to detect whether the product is generated, and stop the reaction after confirming that the reaction is complete. The reaction solution was filtered, the solvent was removed in vacuo, 10ml of EA was added to dissolve, and then washed three times with 2% HCl, 5% NaHCO3, 10ml of H2O respectively, and finally the solvent EA was removed in vacuo to obtain the crude product. The resulting crude product was separated on a silica gel column, eluting with three column volumes of CHCl3. The crude product GX-N was obtained, and then separated on a silica ...
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