Application of cantharidin derivative in preparation of antitumour medicine
A technology of cantharidin derivatives and anti-tumor drugs, which is applied in the direction of anti-tumor drugs, drug combinations, active ingredients of heterocyclic compounds, etc. It can solve the problems of failure to become mainstream anti-cancer drugs, no intellectual property rights, and less research on the mechanism of action. question
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[0016] The processing steps of its synthetic method are:
[0017] The compound CH-01 was dissolved in freshly distilled DMSO, and mixed evenly with KCN, the molar ratio of the compound CH-01 to KCN was 1.0:1.0-3.0. Heating to reflux under constant stirring for 4 to 8 hours. The reaction system was cooled to room temperature and washed with an appropriate amount of 20% H 2 SO 4 acidified to pH=3, then extracted with ethyl acetate, the extract was washed with saturated brine, MgSO 4 Compound CH-02 was obtained by drying, concentrating and purifying by column chromatography.
[0018] The compound CH-03 provided by the present invention, the Chinese name is (2S,3R)-3-(carboxymethyl)-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2 -Carboxylic acid; the English name is (2S, 3R)-3-(carboxymethyl)-2,3-dimethyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid; the molecule is C 11 h 16 o 5 ; Molecular weight is 228.24; Melting point is 232.2~232.3℃; White solid. The structure is as foll...
Embodiment 1
[0038] Compound CH-02 and its synthesis
[0039] Dissolve 91.0 mg (5.0 mmol) of CH-01 in freshly distilled DMSO (10.0 mL) and mix well with 97.5 mg (15.0 mmol) of KCN, and heat to reflux in an oil bath for 5 hours while stirring continuously. The reaction system was cooled at room temperature, and 20% H 2 SO 4 acidified to pH=3, then extracted with ethyl acetate, the organic phase was washed with saturated brine, MgSO 4 Drying, concentration, and purification by column chromatography yielded 30.9 mg of a white solid. The yield was 29.6%. The product was analyzed by elemental analysis, IR spectrum, 1 H NMR spectrum, MS spectrum determination. The analysis results are as follows:
[0040] Elemental analysis (calculated value / measured value) (%): C 63.14 / 63.05, H 7.23 / 7.48, N 6.69 / 6.58;
[0041] IR spectrum (KBr): 2982.4, 2235.7, 1709.9, 1689.2, 1481.1, 1446.1, 1266.6, 1164.3, 1126.2, 1006.9, 932.4, 879.1, 817.3, 588.4, 469.2cm -1 ;
[0042] 1H NMR spectrum (300MHz, CDC...
Embodiment 2
[0045] Compound CH-03 and its synthesis
[0046] In a 25mL round-bottomed flask, put CH-02209.2mg (1.0mmol), add 10.0mL of concentrated hydrochloric acid at room temperature to dissolve it, heat up the oil bath slowly, and reflux for 8 hours. A white solid gradually precipitated out in the system. The mixture was filtered. The solid was washed with water and dried in vacuo; the filtrate was extracted with ethyl acetate and concentrated to obtain a white solid. The two obtained solids were combined and purified by column chromatography to obtain 134.0 mg of white solid. The yield was 58.7%. Product by IR spectrum, 1 H NMR spectrum, MS spectrum determination. The analysis results are as follows:
[0047] IR spectrum (KBr): 3065.9, 2975.6, 1754.9, 1722.6, 1348.6, 1279.1, 1200.5, 1160.6, 1085.8, 992.3, 928.5, 853.8, 742.1, 653.8, 552.4cm -1 ;
[0048] 1 H NMR spectrum (300MHz, d 6 -Acetone), δ: 1.19(s, 3H), 1.41(s, 3H), 1.95(d, J=16.8Hz, 1H), 1.62~2.31(m, 4H), 3.27(d, J=1...
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