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A water-soluble derivative of a stilbene compound and its preparation method and use
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A stilbene-based, water-soluble technology, which is applied in the field of preparing antitumor drugs, can solve the problems of weak water solubility and increased cost, and achieve the effects of low cost, high efficiency, and simple and reliable preparation methods
Inactive Publication Date: 2016-12-14
FUDAN UNIV
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[0003] Some studies have isolated the compound trans-4-[2-(3,5-dimethoxyphenyl)vinyl] from Sphaerophysa salsula (Pall.) DC. -1,2-benzenediol, as shown by tests, has obvious anti-tumor effect (ZL 200710041994.1, ZL200710041995.6); however, practice shows that due to the relatively weak water solubility of the compound, it is limited by the characteristics of the compound itself Restrictions, significantly increase the cost in drug development and application, therefore, it is necessary to research and develop derivatives of such compounds with water solubility, in order to facilitate their application in the field of drugs
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Embodiment 1
[0038] Preparation of Trans-4-[2-(3,5-dimethoxyphenyl)vinyl]-1,2-benzenediol phosphate disodium salt
[0039] Add (O-tert-butyl)-Trans-4-[2-(3,5-dimethoxyphenyl)vinyl]-1,2-benzenediol phosphate 10g, methanol 100 mL to 500 mL reaction In the bottle, feed an appropriate amount of dry hydrogen chloride gas, raise the temperature to 40-50 degrees to react for 24 hours, filter, remove the solvent under reduced pressure, and recrystallize the product with acetone to obtain the phosphate ester of the compound, filter, dry, and use 2 M NaOH in Form a salt in methanol, filter, add acetone to precipitate a white solid, and dry to obtain 6.1 g of the product. The obtained compound was analyzed by nuclear magnetic resonance, and the results are shown in Table 1.
[0040] Table 1 NMR data of Trans-4-[2-(3,5-dimethoxyphenyl)vinyl]-1,2-benzenediol phosphate disodium salt
[0041] ( 1 H NMR 500 MHz, 13 C NMR 500 MHz in CDCl 3 middle)
[0042] serial number
Embodiment 2
[0043] Example 2 In vitro antitumor effect test of Trans-4-[2-(3,5-dimethoxyphenyl)vinyl]-1,2-benzenediol phosphate disodium salt
[0044] Take the cells in the logarithmic phase 3×10 per well 4 Inoculated on a 96-well plate, discarded the supernatant after 12 hours, and administered according to the following groups: the normal control group and the drug-dosed group (concentration 0-100 μM), each group was provided with 6 duplicate wells, cultured for 24 hours, and the supernatant was discarded. Add 50 μl of culture solution with MTT and incubate for 4 hours (0.5 mg / mL), add 100 μl DMSO, shake for 1 hour, and measure the OD value at 570 nm on a microplate reader.
[0045]The results showed that after adding the drug, the cell activity decreased obviously, and the cell activity decreased with the increase of the drug concentration. IC50 for SF188 (glioma cells), HGC-27 (gastric cancer cells), MCF-7wt (breast cancer cells), H460 (large cell lung cancer cells) (cell lines were ...
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Abstract
The invention belongs to the field of antitumor compounds, and relates to a water-soluble derivative of a stilbene compound, in particular to trans-4-[2-(3,5-dimethoxyphenyl)vinyl] of formula I ‑1, 2‑benzenediol water-soluble derivatives, their preparation method and their application in the preparation of antitumor drugs. The present invention uses the compound Trans-4-[2-(3,5-disubstituent phenyl)vinyl]-1,2-benzenediol as the mother nucleus to carry out water-soluble transformation to obtain the stilbene compound water soluble derivatives. The results of in vitro anti-tumor tests show that the water-soluble derivatives of stilbene compounds of the present invention have obvious inhibitory effects on glioma cells SF188, U87wt, breast cancer cells MCF‑7wt, and large cell lung cancer cells H460 , the cell viability decreased with increasing drug concentration. The compound of the present invention is an effective antitumor agent, and further, the compound of the present invention can be used to prepare antitumor drugs. I.
Description
technical field [0001] The invention belongs to the field of antitumor compounds, and relates to a water-soluble derivative of a stilbene compound, in particular to trans-4-[2-(3,5-dimethoxyphenyl)vinyl]-1, 2-Benzene glycol water-soluble derivatives, their preparation method and their application in the preparation of antitumor drugs. Background technique [0002] According to reports, more than 6 million people die of various cancers every year in the world, and 8 million new cases are reported, and the data is still increasing year by year. There are millions of new cancer patients in our country every year, about 2 million patients waiting for treatment, and more than 1 million deaths. Cancer has become the first cause of death. Therefore, the research and preparation of antitumor drugs has become a hot spot in the field of biomedicine. [0003] Some studies have isolated the compound trans-4-[2-(3,5-dimethoxyphenyl)vinyl] from Sphaerophysa salsula (Pall.) DC. -1,2-ben...
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