Curcumenol derivatives and application of curcumenol derivatives in preparing antitumor drug
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A technology of curcumol and its derivatives, applied in the field of medicine, can solve the problems of clinical application limitations, poor water solubility of curcumol, etc.
Active Publication Date: 2018-02-27
同写意(北京)科技发展有限公司
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[0004] Curcumol is one of the important substances of zedoary volatile oil. At present, there have been many studies on its anti-tumor pharmacological effects. Related studies have shown that zedoary can not only directly destroy
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Embodiment 1
[0033] The preparation of embodiment 1 curcumol derivative
[0034] The preparation scheme is as follows:
[0035]
[0036] 1. Furfurylamine (25mmol), put it in an eggplant-shaped bottle, add dry tetrahydrofuran to it, add triethylamine (75mmol) as an acid-binding agent, place it on a magnetic stirrer, and slowly add chlorinated acetyl chloride dropwise to it at room temperature (37.5mmol) of tetrahydrofuran solution with constant stirring, 1h dropwise addition is completed, and the reaction is continued at room temperature. The ester layer was backwashed with saturated aqueous sodium chloride solution, dried with an appropriate amount of anhydrous magnesium sulfate, filtered after 1 h, concentrated under reduced pressure to obtain a tan crude product, and dried in a vacuum oven to obtain compound 1, which was directly put into the next reaction.
[0037] 2. Add curcumol (5mmol) into an eggplant-shaped bottle, add dry tetrahydrofuran and stir to dissolve, weigh sodium hydr...
Embodiment 2
[0044] Embodiment 2: in vitro antitumor activity experiment
[0045] Select part of the curcumol derivatives synthesized in Example 1 to carry out in vitro anti-tumor activity experiments, respectively select HepG2 (human liver cancer cells), Hela (human cervical cancer cells), A549 (human lung cancer cells) cell lines, and use MTT (3- (4,5-dimethylthiazole-2)-2,5-diphenyltetrazolium bromide) reduction method was used to determine the inhibitory activity of curcumol-3-substituted ether derivatives on three human cancer cell lines, And calculate the drug concentration when the inhibition rate reaches 50%, ie the IC50 value, and use 5-fluorouracil as the positive control.
[0046] Tumor cells in the logarithmic growth phase were selected, digested with trypsin, and mixed with RPMI 1640 medium to make 6×10 4 / mL of cell suspension, and then add the cell suspension to 96-well culture plate, 37°C, 5% CO 2 Conditioned for 24 hours. Add the pre-configured drugs with different conc...
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Abstract
The invention relates to curcumenol derivatives and application of the curcumenol derivatives in preparing an antitumor drug. By performing structure modification on the curcumenol derivatives, aftera furfuryl amine fragment is introduced at a hydroxy group site of curcumenol, amine is further introduced through Mannich reaction to obtain a series of the curcumenol derivatives of a structure of aformula (I) as well as pharmaceutically acceptable salts, hydrates, solvates or prodrugs of the curcumenol derivatives which are not reported. Verified by an in vitro bioactivity experiment, the newcurcumenol derivatives have the inhibitory activity to a cervical cancer, a liver cancer, a lung cancer and the like, and the compound activity of most of the new curcumenol derivatives are remarkablyhigher than that of curcumenol as a parent of the new curcumenol derivatives. In addition, the polarity of the vast majority of the synthesized curcumenol derivatives is remarkably improved comparedwith the curcumenol; according to the similarity and intermiscibility principle, the phenomenon that the solubility of the synthesized curcumenol derivatives is higher than that of the curcumenol of aparent compound is proved to a certain degree, and a basic theoretical basis is provided for better performing preparation research and exerting efficacy. The formula (I) is shown in the description.
Description
technical field [0001] The invention relates to the technical field of medicine, more specifically to derivatives of curcumol, methods for preparing derivatives of curcumol and applications of derivatives of curcumol. The method is to modify the structure of curcumol monomer with anti-tumor activity to obtain a series of curcumol derivatives with better curative effect. Background technique [0002] Tumor is a serious threat to human life and health, and its mortality rate ranks second, second only to cardiovascular disease, which has the highest mortality rate. The International Cancer Research Center predicts that in the next 20 years or so, the number of deaths from cancer worldwide will rise to 13 million per year, and the number of new cancer cases will rise to 22 million per year. Tumor will become a major problem in disease prevention and control in the future, and the situation is becoming more and more severe. By 2050, the number of cases is expected to rise to 23....
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