CN112062743B - Resveratrol derivative and application thereof - Google Patents
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Abstract
The invention provides a resveratrol derivative shown in a formula (II), wherein R in the formula (II) 1 Is hydroxy, halogen, C 1 ～C 4 Alkyl, or C 1 ～C 4 When methoxy radical, R 2 Is H; r 1 When is H, R 2 Is halogen; particular preference is given to R 1 Is hydroxy, halogen, C 1 ～C 4 Alkyl or C 1 ～C 4 When methoxy radical, R 2 Is H. The invention provides a novel compound resveratrol derivative and a preparation method thereof, the operation process is simple, the raw material sources are commercialized and easily obtained, and the inhibition effect of the resveratrol derivative is obviously improved compared with that of resveratrol and 7-hydroxycoumarin. Compared with the prior method for modifying resveratrol, the reaction is completed in one step, and is more direct, efficient and quick.
Description
(I) technical field
The invention relates to a resveratrol derivative and a preparation method and application thereof.
(II) background of the invention
Tumor is a new organism formed by abnormal proliferation and differentiation caused by the loss of normal regulation and control of local tissue cells on the gene level under the action of various tumorigenic factors. The tumor has the characteristics of quick growth, easy transfer, difficult radical cure, high lethality and the like, and is a serious disease seriously threatening the life safety of human beings.
Resveratrol (3, 4', 5-trihydroxy-1, 2-stilbene) is a non-flavonoid polyphenol compound produced by various plants, is a natural polyphenol drug with wide action, is a phytoalexin produced when plants suffer from external stress, mainly exists in berry plants such as grapes and is found in 100 plants at present. Research in recent years shows that resveratrol has various biological activities and pharmacological effects, especially has very obvious effects on oxidation resistance, tumor resistance, inflammation resistance and protection of nervous and cardiovascular diseases, and can be widely applied to the fields of medicines, foods, cosmetics, health care products and the like. However, low bioavailability prevents their therapeutic use, and therefore, resveratrol derivatives or analogues based on stilbene are receiving more attention, which have higher bioavailability and lower biotoxicity than resveratrol but are complicated to react.
Disclosure of the invention
In order to solve the problems of low bioavailability, complex preparation process of the resveratrol derivative or the analogue and the like of the existing resveratrol, the invention provides the resveratrol derivative with high bioavailability and good antitumor activity, and the method for preparing the resveratrol derivative with the coumarin structure by only one step is simple, efficient and convenient.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a resveratrol derivative shown in a formula (II),
in the formula (II), R 1 Is hydroxy, halogen, C 1 ～C 4 Alkyl or C 1 ～C 4 Methoxy radical, R 2 Is H.
Preferably, the resveratrol derivative shown in the formula (II) is one of the following:
the preparation route of the resveratrol derivative is as follows:
specifically, the preparation method of the resveratrol derivative shown in the formula (II) comprises the following steps: adding a compound shown as a formula (I) into a solvent, reacting with an olefin compound at 60-100 ℃ for 6-8 h under the conditions of a catalyst, an oxidant and an additive, and after the reaction is finished, carrying out post-treatment on the obtained reaction liquid to obtain a resveratrol derivative shown as a formula (II);
in the formula (I), R 1 Is hydroxy, halogen, C 1 ～C 4 Alkyl or C 1 ～C 4 Methoxy radical, R 2 Is H; the solvent is acetic acid, the catalyst is palladium bis (acetylacetonate), the oxidant is silver acetate, the additive is potassium persulfate, and the olefin compound is methyl acrylate; the ratio of the amount of the catalyst, the oxidant, the additive, the olefin compound and the compound shown in the formula (I) is 0.05-0.1.
Further, the volume of the solvent is 6 to 11mL/mmol based on the amount of the substance of the compound represented by the formula (I).
Further, the amount ratio of the catalyst, oxidant, additive, olefin compound to the substance of the compound represented by formula (I) is 0.1.2.
Further, the post-treatment is as follows: adding saturated NaCl aqueous solution into the reaction solution, extracting for 3 times by using ethyl acetate, wherein the volume of the ethyl acetate is 94-165 mL/mmol based on the substance of the compound shown in the formula (I) each time, combining organic phases, drying by using anhydrous sodium sulfate, filtering, and rotationally evaporating at 40 ℃ to remove the solvent to obtain a crude product containing the compound shown in the formula (II); and (3) performing silica gel column chromatography on the crude product, wherein the volume ratio is 8:1, adopting dichloromethane and methanol solution as mobile phase, tracking and collecting eluent with Rf value of 0.3-0.5 by TLC, collecting obtained eluent, removing solvent under reduced pressure, and drying to obtain resveratrol derivative shown in formula (II).
The invention also provides application of the resveratrol derivative shown in the formula (II) in preparing an anti-tumor medicament.
Further, the tumor is a tumor associated with Hela cells.
More preferably, the resveratrol derivative shown in the formula (II) is one of the compounds shown in the formulae (II-1) to (II-4).
More preferably, the resveratrol derivative shown in the formula (II) is an application of a compound shown in the formula (II-3) in preparing a tumor medicament related to Hela cells.
Compared with the prior art, the invention has the following beneficial effects:
(1) The invention provides a novel compound resveratrol derivative and application thereof, the operation process is simple, the raw material sources are commercialized and easily obtained, and the synthesized novel compound has the antitumor proliferation activity of the resveratrol drug derivative modified by para-chlorine atoms, and the II-3 compound (the concentration is 7.82 +/-0.4) has the optimal inhibition effect which is improved by about 2 times compared with the optimal inhibition effect of resveratrol and is improved by about 2.7 times compared with the optimal inhibition effect of 7-hydroxycoumarin.
(2) Compared with the prior method for modifying resveratrol, the reaction is completed in one step, and is more direct, efficient and quick.
(IV) description of the drawings
FIGS. 1 and 2 are a hydrogen nuclear magnetic spectrum and a mass spectrum of the compound II-1 in example 1, respectively;
FIGS. 3 and 4 are the hydrogen nuclear magnetism and mass spectra of compound I-2 in example 3, respectively;
FIGS. 5 and 6 are the hydrogen nuclear magnetism and mass spectra of the compound II-2 in example 3, respectively;
FIGS. 7 and 8 are the hydrogen nuclear magnetism and mass spectra of compound I-3 in example 5, respectively;
FIGS. 9 and 10 are a hydrogen nuclear magnetic spectrum and a mass spectrum of the compound II-3 in example 5, respectively;
FIGS. 11 and 12 are the hydrogen nuclear magnetism and mass spectra of compound I-4 in example 7, respectively;
FIGS. 13 and 14 are a hydrogen nuclear magnetism spectrum and a mass spectrum of compound II-4 of example 7, respectively.
(V) detailed description of the preferred embodiments
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
the technical solution of the present invention is illustrated by the following specific examples, but the scope of the present invention is not limited thereto:
example 1: preparation of resveratrol derivative II-1
50mg (0.22 mmol) of resveratrol I-1 was added to 2ml of an acetic acid solvent, and 6.7mg (0.022 mmol) of palladium bis (acetylacetonate) was added thereto; 44mg (0.264 mmol) of silver acetate; 71mg (0.264 mmol) of potassium persulfate, 23mg (0.264 mmol) of methyl acrylate; reacting at 100 ℃ for 8h, adding 60ml of saturated NaCl aqueous solution into the reaction solution after the reaction is finished, extracting with ethyl acetate for 30ml each time, collecting an organic phase after 3 times of extraction, drying an organic layer with anhydrous sodium sulfate, filtering, and rotationally evaporating at 40 ℃ to remove the solvent to obtain a crude product II-1; and (3) performing silica gel column chromatography on the II-1 crude product, wherein the volume ratio is 8:1 as mobile phase, collecting eluate with Rf value of 0.3-0.5 by TLC tracking, removing solvent under reduced pressure, drying, and drying to obtain 14.9mg of compound shown in formula II-1.
Yellow solid, yield 24.2%.1H NMR (600mhz, dmso) δ 8.48 (d, J =9.7hz, 1h), 7.58 (d, J =8.6hz, 2h), 7.51 (d, J =16.1hz, 1h), 7.15 (d, J =16.0hz, 1h), 7.09 (d, J =2.2hz, 1h), 6.80 ((d, J =8.6hz, 2h), 6.64 (d, J =2.1hz, 1h), 6.22 (d, J =9.8hz, 1h), ESI + :Calculated for C 17 H 12 O 4 :[M+H] + 281.02,found 280.1。
Example 2: preparation of resveratrol derivative II-1
The same procedures as in example 1 were repeated except that the mass and mole of bis (acetylacetonate) palladium were changed to 3.04mg (0.01 mmol), the temperature was changed to 60 ℃ and the reaction time was changed to 6 hours, to obtain 4.76mg of a pure compound represented by the formula (II-1) in a reaction yield of 7.72%.
Example 3: preparation of resveratrol analog II-2
189mg (1 mmol) of 5-bromoresorcinol are added to 4ml of acetonitrile, 35mg (0.05 mmol) of bis-triphenylphosphonium dichloropalladium, 303mg (3 mmol) of triethylamine are added thereto, and finally 312mg (3 mmol) of a solution containing 4-methylstyrene, N 2 Protection, 110 deg.CReacting for 4h, after the reaction is finished, adding 60ml of saturated NaCl aqueous solution into the reaction solution, extracting with ethyl acetate for 3 times (30 ml each time), collecting an organic phase, drying an organic layer by anhydrous sodium sulfate, filtering, and rotationally evaporating at 40 ℃ to remove the solvent to obtain a crude product I-2; and (3) performing silica gel column chromatography on the I-2 crude product, wherein the volume ratio is 4:1 as mobile phase, collecting eluate with Rf value of 0.3-0.5 by TLC tracking, removing solvent under reduced pressure, drying, and drying to obtain 27.6mg of compound shown in formula I-2.
White solid, yield 17%.1H NMR (600mhz, dmso) δ 9.24 (s, 2H), 7.47 (d, J =7.8hz, 2h), 7.17 (d, J =7.8hz, 2h), 7.00 (s, 2H), 6.43 (s, 2H), 6.15 (s, 1H), 2.31 (s, 3H). ESI + :Calculated for C 15 H 14 O 2 :[M-H] - 225.12,found 226.3。
40mg (0.18 mmol) of Compound I-2 was added to 2ml of an acetic acid solvent, and 5.5mg (0.018 mmol) of palladium bis (acetylacetonate) was added thereto; 33.4mg (0.2 mmol) of silver acetate; 54mg (0.2 mmol) of potassium persulfate, 17.2mg (0.2 mmol) of methyl acrylate; reacting at 100 ℃ for 8h, adding 60ml of saturated NaCl aqueous solution into the reaction solution after the reaction is finished, extracting with ethyl acetate for 30ml each time, collecting an organic phase after 3 times of extraction, drying an organic layer by anhydrous sodium sulfate, filtering, and rotationally evaporating at 40 ℃ to remove the solvent to obtain a crude product II-2; and (3) performing silica gel column chromatography on the II-2 crude product, wherein the volume ratio is 8:1 as mobile phase, collecting eluate with Rf value of 0.3-0.5 by TLC tracking, removing solvent under reduced pressure, drying, and drying to obtain 13.6mg of compound shown in formula II-2.
Yellow solid, yield 27.8%.1H NMR (600mhz, cdcl3) δ 8.08 (d, J =9.7hz, 1h), 7.45 (d, J =7.8hz, 2h), 7.36 (d, J =16.0hz, 1h), 7.28 (s, 1H), 7.22 (d, J =7.8hz, 2h), 7.08 (d, J =12.8hz, 2h), 6.86 (s, 1H), 6.30 (d, J =9.7hz, 1h), 2.41 (s, 3H). ESI + :Calculated for C 18 H 14 O 3 :[M-H] - 277.21,found 278.1。
Example 4: preparation of resveratrol analog II-2
The procedure of example 3 was repeated except that the mass and mole of palladium bis (acetylacetonate) were changed to 2.736mg (0.009 mmol), the reaction temperature for the synthesis of the compound (II-2) was changed to 60 ℃ and the reaction time was changed to 6 hours in the method for the synthesis of the compound (II-2), to obtain 3.47mg of a pure compound represented by the formula (II-2) with a reaction yield of 6.93%.
Example 5: preparation of resveratrol analog II-3
189mg (1 mmol) of 5-bromoresorcinol are added to 4ml of acetonitrile, 35.05 (0.05 mmol) of bis-triphenylphosphonium dichloropalladium, 303mg (3 mmol) of triethylamine are added thereto, and finally 415.8mg (3 mmol) of a solution containing 4-chlorostyrene, N 2 Protecting, reacting at 110 ℃ for 4h, adding 60ml of saturated NaCl aqueous solution into reaction liquid after the reaction is finished, extracting with ethyl acetate for 30ml each time, collecting an organic phase after 3 times of extraction, drying and filtering an organic layer by anhydrous sodium sulfate, and rotationally evaporating at 40 ℃ to remove a solvent to obtain a crude product I-3; and (3) performing silica gel column chromatography on the I-3 crude product, wherein the volume ratio is 4:1 is used as a mobile phase, TLC tracks and collects the eluent with Rf value of 0.3-0.5, and the obtained eluent is decompressed to remove the solvent, dried and dried to obtain 85.9mg of the compound shown in the formula I-3.
White solid, yield 34.8%.1H NMR (400mhz, dmso) δ 7.61 (d, J =8.5hz, 2h), 7.41 (d, J =8.5hz, 2h), 7.09 (d, J =16.4hz, 1h), 7.03 (d, J =16.4hz, 1h), 6.45 (d, J =2.1hz, 1h), 6.18 (d, J =2.2hz, 1h). ESI + :Calculated for C 14 H 11 ClO 2 :[M-H] - 245.09,found 246.0。
78mg (0.32 mmol) of Compound I-3 was added to 2ml of an acetic acid solvent, and 9.7mg (0.032 mmol) of palladium bis (acetylacetonate) was added thereto; 64mg (0.384 mmol) of silver acetate; 103.8mg (0.384 mmol) of potassium persulfate, 33mg (0.384 mmol) of methyl acrylate; reacting at 100 ℃ for 8h, adding 60ml of saturated NaCl aqueous solution into the reaction solution after the reaction is finished, extracting with ethyl acetate for 30ml each time, collecting an organic phase after 3 times of extraction, drying an organic layer by anhydrous sodium sulfate, filtering, and rotationally evaporating at 40 ℃ to remove the solvent to obtain a crude product II-3; and (3) performing silica gel column chromatography on the II-3 crude product, wherein the volume ratio is 8:1 as mobile phase, collecting eluate with Rf value of 0.3-0.5 by TLC tracking, removing solvent under reduced pressure, drying, and drying to obtain 20.5mg of compound shown in formula II-3.
Yellow solid, yield 21.4%.1H NMR (600mhz, dmso) δ 8.39 (d, J =9.7hz, 1h), 7.76 (d, J =8.5hz, 2h), 7.71 (d, J =16.1hz, 1h), 7.44 (d, J =8.5hz, 2h), 7.18 (d, J =16.1hz, 1h), 7.02 (d, J =1.9hz, 1h), 6.52 (d, J =1.6hz, 1h), 6.02 (d, J =9.6hz, 1h), 5.76 (s, 1H). ESI + :Calculated for C 17 H 11 ClO 3 :[M-H] - 297.13,found 298.7。
Example 6: preparation of resveratrol analog II-3
The procedure of example 5 was repeated except that the mass and mole of palladium bis (acetylacetonate) were changed to 4.864mg (0.016 mmol), the reaction temperature for synthesizing the compound (II-3) was changed to 60 ℃ and the reaction time was changed to 6 hours in the method for synthesizing the compound (II-3), whereby 2.27mg of the pure compound represented by the formula (II-4) was obtained in a reaction yield of 2.37%.
Example 7: preparation of resveratrol analog II-4
189mg (1 mmol) of 5-bromoresorcinol are added to 4ml of acetonitrile, 35.05mg (0.05 mmol) of bistriphenylphosphine dichloropalladium, 303mg (3 mmol) of triethylamine and finally 415.8mg (3 mmol) of 3-chlorostyrene, N 2 Protecting, reacting at 110 ℃ for 4h, adding 60ml of saturated NaCl aqueous solution into reaction liquid after complete reaction, extracting with ethyl acetate for 30ml each time, collecting an organic phase after 3 times of extraction, drying an organic layer by anhydrous sodium sulfate, filtering, and rotationally evaporating at 40 ℃ to remove the solvent to obtain a crude product I-4; and (3) performing silica gel column chromatography on the I-4 crude product, wherein the volume ratio is 4:1, taking the solution of petroleum ether and ethyl acetate as a mobile phase, tracking and collecting the eluent with Rf value of 0.3-0.5 by TLC, decompressing and removing the solvent of the collected eluentDrying to obtain 74.7mg of compound shown in formula I-4.
White solid, yield 30.3%.1H NMR (400mhz, dmso) δ 7.68 (s, 1H), 7.55 (d, J =7.8hz, 1h), 7.38 (t, J =7.8hz, 1h), 7.30 (dd, J =7.9,1.0hz, 1h), 7.16 (d, J =16.4hz, 1h), 7.03 (d, J =16.4hz, 1h), 6.46 (t, J =2.9hz, 2h), 6.18 (d, J =2.2hz, 1h). ESI + :Calculated for C 14 H 11 ClO 2 :[M-H] - 245.14,found 246.7。
69mg (0.28 mmol) of Compound I-4 was added to 2ml of an acetic acid solvent, and 8.5mg (0.028 mmol) of bis (acetylacetonato) palladium was added thereto; 56mg (0.336 mmol) of silver acetate; 90.8mg (0.336 mmol) of potassium persulfate, 29mg (0.336 mmol) of methyl acrylate; reacting at 100 ℃ for 8h, adding 60ml of saturated NaCl aqueous solution into the reaction solution after the reaction is finished, extracting with ethyl acetate for 30ml each time, collecting an organic phase after 3 times of extraction, drying an organic layer by anhydrous sodium sulfate, filtering, and rotationally evaporating at 40 ℃ to remove the solvent to obtain a crude product II-4; and (3) performing silica gel column chromatography on the II-4 crude product, wherein the volume ratio is 8:1 as a mobile phase, collecting the eluent with Rf value of 0.3-0.5 by TLC tracking, removing solvent from the collected eluent under reduced pressure, drying, and drying to obtain 17.4mg of the compound shown in formula II-4.
Yellow solid, yield 20.8%.1H NMR (600mhz, dmso) δ 8.44 (dd, J =11.2,5.5hz, 1h), 7.88 (s, 1H), 7.77 (d, J =16.1hz, 1h), 7.65 (d, J =7.7hz, 1h), 7.41 (t, J =7.8hz, 1h), 7.34 (d, J =7.9hz, 1h), 7.17 (d, J =16.0hz, 1h), 7.04 (s, 1H), 6.56 (s, 1H), 6.04 (d, J =9.7hz, 1h). ESI + :Calculated for C 17 H 11 ClO 3 :[M-H] - 297.14,found 298.7。
Example 8: preparation of resveratrol analog II-4
The procedure of example 7 was repeated except that the mass and mole of palladium bis (acetylacetonate) were changed to 4.256mg (0.014 mmol), the reaction temperature for synthesizing the compound (II-4) was changed to 60 ℃ and the reaction time was changed to 6 hours in the method for synthesizing the compound (II-4), thereby obtaining 3.72mg of a pure compound represented by the formula (II-4) with a reaction yield of 3.9%.
Example 9: antitumor detection of resveratrol drug analogs
Selecting tumor cell Hela (cervical cancer cell) and adopting MTT method to detect the proliferation activity of the anti-tumor cell. Cells were seeded at a concentration of 4000-5000 cells/well into 96-well plates containing 1640 culture medium of 10% fetal bovine serum, and the plate lids were annotated, and the ratio of CO was 5% 2 Culturing at 37 ℃ for 12 hours, allowing the cells to adhere to the surface of a 96-well plate, adding the test drug (the compound prepared in example II-1-II-4) to each well in a sterile operating table using a pipetting gun so that the drug concentration in each well is 0.01. Mu.M, 0.1. Mu.M, 1. Mu.M, 10. Mu.M, 100. Mu.M, five concentration gradients are set at each concentration, each concentration being set to five parallel groups, using resveratrol and 7-hydroxycoumarin as controls, and setting the 96-well plate again at 5% CO 2 And incubated at 37 ℃ for 24 hours. The 96-well plate was taken out, 10. Mu.L of MTT kit reagent (purchased from Promega) was added to each well, and the resulting mixture was protected from light to 5% CO 2 Incubating for 4 hours at 37 ℃, absorbing supernatant, adding 150uL sterile DMSO to dissolve formazan, further dissolving in an incubator at 37 ℃ for 5-10min, and finally measuring the absorbance by using an enzyme-labeling instrument. Thereby calculating the cytostatic rate and cytotoxicity, processing with ICE stimulator software, calculating IC 50 And IC 50 The results are shown in Table 1, with a 95% confidence interval.
The results show that: (1) the resveratrol drug derivatives modified by different substituents have certain antitumor activity on Hela (cervical carcinoma cells) and have certain biological significance. (2) The anti-tumor proliferation activity of the resveratrol drug derivative modified by para-chlorine atoms, the II-3 compound (the concentration is 7.82 +/-0.4) has the optimal inhibition effect, which is improved by about 2 times compared with the optimal inhibition effect of resveratrol, and is improved by about 2.7 times compared with the optimal inhibition effect of 7-hydroxycoumarin.
TABLE 1 antitumor Activity of resveratrol drug derivatives
Claims (6)
1. A resveratrol derivative represented by formula (II),
in the formula (II), R 1 Is hydroxy, halogen, C 1 ～C 4 Alkyl or C 1 ～C 4 Methoxy radical, R 2 Is H.
2. A resveratrol derivative of formula (ii) as claimed in claim 1 wherein: the resveratrol derivative shown in the formula (II) is one of the following:
3. the use of the resveratrol derivative according to claim 1 or 2 in preparing an anti-tumor medicament.
4. A use as claimed in claim 3, wherein: the tumor is a tumor associated with Hela cells.
5. Use according to claim 3 or 4, characterized in that: the resveratrol derivative is one of the compounds shown in formulas (II-1) to (II-4).
6. Use according to claim 3 or 4, characterized in that: the resveratrol derivative is a compound shown as a formula (II-3).
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| "6-或7-（取代苯乙烯基）香豆素类化合物的合成及其抗癌活性的研究";徐嵩等;《药学学报》;20001231;第35卷;第103-107页 * |
| Daniel Cha＇vez et al.."Novel stilbenes isolated from the root bark of Ekebergia benguelensis".《Tetrahedron Letters》.2001,第42卷第3685-3688页. * |
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