12-p-methyl benzene acyloxy-14-deoxidized andrographolide photoaffinity labeling molecular probe, and preparation method and pharmaceutical composition thereof
A technology of tolyloxy and andrographolide, applied in the field of 12-p-tolyloxy-14-deoxyandrographolide photoaffinity labeling molecular probe, preparation and pharmaceutical composition thereof, capable of Solve the problem that the mechanism of action of the target protein is not fully elucidated
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Embodiment 1
[0049] Compound III 1 preparation of
[0050] 1.0g II was dissolved in 130mL dichloromethane, and 0.483g K was added 2 CO 3 , stirred magnetically at room temperature for 30 min, then slowly added 0.474 g of bromoacetyl chloride dropwise, and reacted at room temperature for 3 h. After the reaction was completed, it was washed with saturated brine (50mL×3), dried over anhydrous magnesium sulfate, and separated by silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =1:1), to obtain 1.071g compound III 1 , yield 85%. 1 H-NMR (CDCl 3 , 400MHz) δ: 7.92 (2H, d, J = 8.0Hz, ph), 7.39 (1H, s, H-14), 7.24 (2H, d, J = 8.0Hz, ph), 5.89 (1H, t, J=20.0Hz, H-12), 4.92(1H, s, H-17a), 4.83(3H, s, H-15, H-17b), 4.56(1H, d, J=12.0Hz, H-19a ), 4.26 (1H, d, J=12.0Hz, H-19b), 3.86 (2H, s, 19-CO CH 2 Br), 3.36(1H, dd, J=8.0Hz, 4.0Hz, H-3), 2.51~2.45(1H, H-11a), 2.39(3H, s, ph- CH 3 ), 2.26~2.19(4H, -OH, 7a, 9, 11b), 2.08~2.02(1H, H-7b), 1.83~1.50(7H, H-1, 2, 5, 6), 1.22(3H, overlapped-signa...
Embodiment 2
[0060] Compound V 1 preparation of
[0061] 0.5 g compound III 1 Dissolve in 50mL acetone, add 0.152g K 2 CO 3 , stirred magnetically at room temperature for 30 min, then gradually added 0.225 g of photoaffinity labeling group IV, and stirred magnetically at room temperature for 4 h. After the reaction is complete, pour the reaction solution into a beaker containing 100 mL of saturated sodium bicarbonate solution, extract with dichloromethane (100 mL×3), and then use saturated sodium bicarbonate solution (100 mL×3), saturated saline (100 mL×3 ) washing, dried over anhydrous magnesium sulfate, separated by silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =1:1), to obtain 0.579g compound V 1 , yield 91%. 1 H-NMR (CDCl 3 , 400MHz) δ: 8.19 (2H, d, J = 8.0Hz, ph), 7.93 (2H, d, J = 8.0Hz, ph), 7.78 (2H, d, J = 8.0Hz, ph), 7.68 (2H , d, J=8.0Hz, ph), 7.39 (1H, overlapped-signal, H-14), 7.24 (2H, d, J=8.0Hz, ph), 6.68 (2H, d, J=8.0Hz, ph ), 5.89 (1H, t, J=16.0Hz, H-12), 4.92 ...
Embodiment 3
[0071] Preparation of Compound IV
[0072] 5.0g p-nitrobenzoyl chloride was dissolved in 50mL toluene, and 5.04g anhydrous AlCl was added in batches 3 , stirred magnetically at room temperature for 24 h. After the reaction was completed, 50 mL of distilled water was added, stirred magnetically at room temperature for 30 min, washed with saturated sodium bicarbonate solution (30 mL×3), saturated brine (30 mL×3) successively, and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was dissolved in dichloromethane, and petroleum ether was slowly added dropwise until crystals were precipitated, then placed in a refrigerator, filtered, and dried to obtain 5.2 g of a light yellow solid.
[0073] Dissolve the product in 42 mL of acetic acid, add 7.04 g of chromium trioxide in batches, then slowly add 7.3 mL of concentrated sulfuric acid dropwise, and stir magnetically at room temperature for 8 h. After the reaction was completed, the reaction solution wa...
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