Dihydropyridine type tumor chemotherapeutic sensitizer and application thereof
A dihydropyridine and compound technology, applied in the field of dihydropyridine tumor chemotherapy sensitizers, can solve the side effects of cardiovascular system and other problems
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Embodiment 1
[0063] Example 1: 2,6-Dimethyl-4-(3-nitrophenyl)-1-[(oxiranyl)methyl]-1,4-dihydropyridine-3,5-dicarboxy Acid dimethyl ester (intermediate)
[0064] Add 2.31g (57.8mmol) 60% sodium hydrogen and 50mL anhydrous tetrahydrofuran to the reaction flask, stir, and add 10g (28.9mmol) 2,6-dimethyl-4-(3-nitrophenyl) at 0°C -Dimethyl 1,4-dihydropyridine-3,5-dicarboxylate, after no gas is released, add 7.98g (86.7mol) of epichlorohydrin dropwise. After the addition, continue to stir for 0.5h, and react at room temperature for 24h. Slowly add 5 mL of water dropwise, concentrate under reduced pressure, add 20 mL of dichloromethane and 10 mL of water to the residue, stir for 10 min, separate the layers, extract the aqueous layer with 2×5 mL of dichloromethane, combine the organic layers, dry over anhydrous sodium sulfate, and filter. Concentration under reduced pressure, the residue was separated by column chromatography (petroleum ether: ethyl acetate = 3:2) to obtain 5.30 g of light yello...
Embodiment 2
[0065] Example 2: 1-[3-(2-hydroxyethylamino)-2-hydroxypropyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydro Dimethyl pyridine-3,5-dicarboxylate (I 1 )
[0066] Add 0.5g (1.25mmol) 2,6-dimethyl-4-(3-nitrophenyl)-1-[(oxiranyl)methyl]-1,4-dihydropyridine to the reaction flask -Dimethyl 3,5-dicarboxylate, 0.23g (3.75mmol) ethanolamine and 10mL methanol, stirred and refluxed for 5h, concentrated under reduced pressure, and the residue was column chromatographed (petroleum ether: ethyl acetate: triethylamine=30: 6:1) to obtain 500 mg of pale yellow oil, with a yield of 86.8%.
[0067] 1 HNMR (CDCl 3 )δ: 2.43~2.74(m, 4H, CHC H 2 NHC H 2 CH 2 OH), 2.50, 2.55 (2×s, 6H, C 2,6 -CH 3 ), 3.65(t, J=5.1Hz, 2H, CH 2 C H 2 OH), 3.69~3.74 (m, 1H, C H OH), 3.71, 3.73 (2×s, 6H, C 3,5 -COOCH 3 ), 3.84 (m, 2H, NC H 2 CH), 5.21(s, 1H, C 4 -H), 7.39(m, 1H, nitrogenyl 5-H), 7.69(m, 1H, nitrogenyl 6-H), 7.98~8.00(m, 1H, nitrogenyl 4-H), 8.15(m, 1H, nitrogenyl 2 -H)
[0068] ESI-MS(m / ...
Embodiment 3
[0071] Example 3: 1-[(2-Hydroxy-3-n-butylamino)propyl]-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylic acid dimethyl ester (I 2 )
[0072] Refer to I 1 Synthetic method, a light yellow oily substance was obtained with a yield of 90.3%.
[0073] 1 HNMR (CDCl 3 )δ: 0.90 (t, J=7.1Hz, 3H, CH 2 CH 2 CH 2 C H 3 ), 1.30~1.43 (m, 4H, CH 2 C H 2 C H 2 CH 3 ), 2.27~2.55(m, 4H, CHCH 2 NHC H 2 CH 2 CH 2 CH 3 ), 2.49, 2.55 (2×s, 6H, C 2,6 -CH 3 ), 3.57~3.62 (m, 1H, C H OH), 3.71, 3.72 (2×s, 6H, C 3,5 -COOCH 3 ), 3.82 (d, J=5.4Hz, 2H, NC H 2 CH), 5.21(s, 1H, C 4 -H), 7.37(m, 1H, nitrogenyl 5-H), 7.70(m, 1H, nitrogenyl 6-H), 7.97~8.00(m, 1H, nitrogenyl 4-H), 8.15(m, 1H, nitrogenyl 2 -H)
[0074] ESI-MS(m / z): 476[M+H] +
[0075] IR: 3400, 3032, 2948, 1692, 1636, 1577, 1571, 1527, 1430, 1386, 1349, 1203, 1157, 772
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