CN111333495B - (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and preparation method and application thereof - Google Patents
(4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and preparation method and application thereof Download PDFInfo
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- CN111333495B CN111333495B CN202010311435.3A CN202010311435A CN111333495B CN 111333495 B CN111333495 B CN 111333495B CN 202010311435 A CN202010311435 A CN 202010311435A CN 111333495 B CN111333495 B CN 111333495B
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Abstract
The invention provides a new compound (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, a preparation method and application thereof, and the structure thereof is shown as the following formula:
Description
Technical Field
The invention relates to the field of biochemical medicine, in particular to (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, a preparation method and application thereof.
Background
The basic structure of the benzophenone compound is that two benzene rings are respectively connected to two sides of a carbonyl group. The benzene ring may be substituted with alkyl, alkoxy, amino, hydroxyl, etc. The type and position of these substituents can also affect their biological activity. Benzophenone and xanthone are structurally similar. The two benzene rings of xanthone are connected through carbonyl and oxygen atoms to form a conjugated system and a planar structure. The two benzene rings of benzophenone are connected only through carbonyl groups, and can form a conjugated system but not necessarily form a planar structure. Thus, there is a similarity and difference in the biological activity of benzophenone and xanthone compounds.
Various substituents on the phenyl ring of benzophenone determine its biological activities, and the change of one or more substituents can change its biological activities.
(4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone and its use are not disclosed in domestic and foreign literature.
Disclosure of Invention
Therefore, the invention aims to provide a benzophenone compound with certain physiological and pharmacological activities. In order to realize the purpose of the invention, the invention adopts the following technical scheme:
in a first aspect of the present invention, there is provided a novel benzophenone compound (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone, which has the structure shown in formula (i):
in a second aspect of the present invention, there is provided a process for the preparation of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone, comprising the step of reacting 4-methoxy-3-hydroxybenzoic acid with 2, 4-dimethylphenol in an eaton reagent to form a benzophenone compound.
Further, the eaton reagent system is composed of phosphorus pentoxide and methane sulfonic acid, and the molar ratio of the 4-methoxy-3-hydroxybenzoic acid to the 2, 4-dimethylphenol is 1.
Further, the method comprises the following steps: adding phosphorus pentoxide into methanesulfonic acid, and stirring at 110 ℃ to dissolve the phosphorus pentoxide to obtain an Eton reagent; cooling the Eton reagent to 90 ℃, adding equal mass of 4-methoxy-3-hydroxybenzoic acid and 2, 4-dimethylphenol, and continuing to react at 90 ℃; after the reaction is finished, pouring the reaction solution into water, separating out a viscous substance, and extracting to obtain a primary product; the primary product is purified by medium-pressure preparative chromatography to obtain (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone.
In a third aspect of the invention, an application of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone in preparing an anti-tumor medicament is provided.
Furthermore, the tumors comprise leukemia HL-60, lung cancer A-549, liver cancer SMMC-7721, liver cancer HepG2, liver cancer Huh-7, liver cancer SK-HEP-1, liver cancer MHCC97H, liver cancer PLC/PRF/5 breast cancer MCF-7, colon cancer SW480, cervical cancer HeLa, prostate cancer PC-3, breast cancer MDA-MB-231, human neuroblastoma SH-SY5Y and lung cancer Taxol-resistant strain A549/Taxol.
In a fourth aspect of the present invention, there is provided an antitumor agent comprising (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone, or a pharmaceutically acceptable salt or ester thereof as an active ingredient.
The compound (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone shown in the formula I is a novel benzophenone compound, has obvious antitumor activity and can be used for preparing antitumor drugs. In particular to leukemia HL-60, lung cancer A-549, liver cancer SMMC-7721, breast cancer MCF-7, colon cancer SW480, liver cancer HepG2, liver cancer Huh-7, cervical cancer HeLa, prostate cancer PC-3, breast cancer MDA-MB-231, human neuroblastoma SH-SY5Y and lung cancer Taxol-resistant strain A549/Taxol. Meanwhile, the preparation method of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone has the advantages of simple operation, mild reaction condition and higher yield, and can be used for industrial mass preparation.
Detailed Description
In order to explain technical contents, structural features, and objects and effects of the technical means in detail, the following description is given with reference to specific embodiments.
Example 1: synthesis and resolution of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone
Phosphorus pentoxide (0.58g, 4.1 mmol) and methanesulfonic acid (10 mL) were sequentially added to a 25mL round-bottomed flask, heated to 110 ℃ and stirred to dissolve the phosphorus pentoxide and the methanesulfonic acid, and the reaction solution was cooled to 90 ℃ and 4-methoxy-3-hydroxybenzoic acid (0.34g, 2.0 mmol) and 2, 4-dimethylphenol (0.26 mL, 2.0 mmol) were sequentially added and the reaction was continued at 90 ℃ for 0.5h. Lifting the reaction bottle, cooling to room temperature, pouring the reaction solution into a proper amount of water, separating out viscous liquid, extracting with ethyl acetate, combining organic phases, drying with anhydrous sodium sulfate, evaporating under reduced pressure to remove the solvent, and separating and purifying the primary product by medium-pressure preparative chromatography to obtain 50mg of dark green solid, wherein the yield is 9.2%, and the mp is 101-104 ℃. A mixed solvent of ethyl acetate and petroleum ether was used as eluent for medium pressure preparative chromatography.
IR(KBr)v max 552,628,761,790,876,1020,1134,1187,1218,1278, 1361,1423,1510,1564,1609,1728,2852,2918,2955,2976,3013,3288 cm -1 ； 1 H NMR (500 MHz, acetone-d 6 )δ2.22(s,6H,2CH 3 -),3.95(s,3H,CH 3 O-), 7.10(d,1H,J＝8.9Hz,H-5),7.22-7.24(m,2H,H-2,H-6),7.26-7.27 (m,1H,H-4’),7.33(dd,1H,J＝0.7,1.5Hz,H-6’),8.23(s,1H, HO-3),12.04(s,1H,HO-2’)； 13 C NMR (125 MHz, acetone-d) 6 )δ15.5,20.4, 56.3,111.5,116.9,119.2,123.4,127.4,127.7,131.4,131.8,138.5, 147.3,152.1,159.8,201.2。
Example 2: research on antitumor activity of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone
(1) The principle is as follows:
MTS is a novel MTT analogue and is a yellow dye. The succinate dehydrogenase in the mitochondria of the living cells can metabolize and reduce MTS to generate soluble Formazan (Formazan) compounds, and the content of the Formazan can be measured at 490nm by using an enzyme labeling instrument. In general, the amount of formazan produced is proportional to the number of viable cells, and therefore the number of viable cells can be estimated from the optical density OD value.
(2) Experimental method
(1) Inoculating cells: preparing single cell suspension with culture solution (DMEM or RMPI 1640) containing 10% fetal calf serum, inoculating 3000-15000 cells per well into 96-well plate, and inoculating adherent cells in volume of 100 μ l per well for 12-24 hr.
(2) Adding a solution of the test compound: the compound was dissolved in dimethyl sulfoxide (DMSO), and the compound was initially screened at a concentration of 40. Mu.M, with a final volume of 200. Mu.l per well, 3 multiple wells (mixed solution of 20. Mu.l MTS solution and 100. Mu.l culture medium) were provided for each treatment, and incubation was continued for 2-4h to allow the reaction to proceed sufficiently, and then the light absorption value was measured.
(3) Color development: after culturing for 48h at 37 ℃, removing culture solution in each hole of the adherent cells, and adding 20 mul of MTS solution and 100 mul of culture solution into each hole; discarding 100 mul of culture supernatant from the suspension cells, and adding 20 mul of MTS solution into each well; 3 blank double wells (mixed solution of 20. Mu.l MTS solution and 100. Mu.l culture medium) were set, incubation was continued for 2-4h, and the light absorption value was measured after the reaction was sufficiently progressed.
(4) Color comparison: selecting 492nm wavelength, reading the light absorption value of each hole by a multifunctional enzyme labeling instrument (MULTISKAN FC), recording the result, and drawing a tumor cell inhibition percentage graph by taking the compound number as the abscissa and the cell inhibition percentage as the ordinate after data processing.
(5) For tumor cells with a percentage of inhibition of more than 50%, they were rescreened at concentrations of 40. Mu.M, 8. Mu.M, 1.6. Mu.M, 0.32. Mu.M, 0.064. Mu.M, and the IC of the compound on the tumor cells was determined 50 The value is obtained. Two positive compounds of cisplatin (DDP) and paclitaxel (Taxol) are set in each experiment, a cell growth curve is drawn by taking the concentration as the abscissa and the cell survival percentage as the ordinate, and the IC of the compound is calculated by using a two-point method (Reed and Muench method) 50 The value is obtained.
For convenience of description, (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone is abbreviated as compound 1. According to the experimental method of the technical scheme, cisplatin (DDP) and paclitaxel (Taxol) are used as positive control compounds, a small amount of samples are taken and dissolved in DMSO to prepare a 40 mu M solution, and then the inhibitory activity of 15 human tumor cells is detected (tables 1-6).
TABLE 1 inhibitory Activity of Compound 1 at a concentration of 40. Mu.M against 5 cancer cells
TABLE 2 inhibitory Activity of Compound 1 at a concentration of 40. Mu.M on 5 hepatoma cells
TABLE 3 inhibitory Activity of Compound 1 at a concentration of 40. Mu.M against 5 cancer cells
TABLE 4 IC of Compound 1 on 5 cancer cells 50 Value of
TABLE 5 IC of Compound 1 on 2 hepatoma cells 50 Value of
TABLE 6 IC of Compound 1 on 5 additional cancer cells 50 Value of
As can be seen from tables 1-6, the percentage of inhibition of compound 1 on leukemia HL-60, lung cancer A-549, liver cancer SMMC-7721, breast cancer MCF-7, colon cancer SW480, liver cancer (HepG 2 and Huh-7), cervical cancer HeLa, prostate cancer PC-3, breast cancer MDA-MB-231, human neuroblastoma SH-SY5Y and lung cancer paclitaxel resistant strain A549/Taxol exceeds 50%, and IC thereof is IC 50 The value is between 0.111 and 6.87 mu M, so that the (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone has good inhibition effect on the 12 human cancer cells.
As can be seen from tables 4-6, compound 1 is shown to be IC for leukemia HL-60, lung cancer A-549, liver cancer SMMC-7721, breast cancer MCF-7, colon cancer SW480, liver cancer HepG2, cervical cancer HeLa, prostate cancer PC-3, breast cancer MDA-MB-231, human neuroblastoma SH-SY5Y and lung cancer Taxol-resistant strain A549/Taxol 50 Values of 0.122, 2.27, 0.111, 3.06, 1.35, 0.753, 0.577, 0.775, 2.56, 0.613 and 6.02. Mu.M, respectively, while the positive controlThe cisplatin can be used for treating leukemia HL-60, lung cancer A-549, hepatocarcinoma SMMC-7721, breast cancer MCF-7, colon cancer SW480, hepatocarcinoma HepG2, cervical cancer HeLa, prostate cancer PC-3, breast cancer MDA-MB-231, human neuroblastoma SH-SY5Y and IC of lung cancer Taxol-resistant strain A549/Taxol 50 The values were 4.50, 23.55, 12.41, 26.79, 25.43, 8.02, 7.11, 9.22, 4.53, 16.05 and 21.95 μ M, respectively. Thus, IC of Compound 1 on the 11 cancer cells 50 The values are all smaller than that of cisplatin, and the inhibition activities are all greater than that of cisplatin. As can be seen from Table 4, IC of compound 1 and the positive control drug paclitaxel on liver cancer SMMC-7721 50 The values were 0.111 and 0.139. Mu.M, respectively. Therefore, the inhibitory activity of the compound 1 on the liver cancer SMMC-7721 is stronger than that of a classical antitumor drug paclitaxel.
Particularly emphasized is the IC of compound 1 on leukemia HL-60, liver cancer SMMC-7721, liver cancer HepG2, cervical cancer HeLa, prostate cancer PC-3 and human neuroblastoma SH-SY5Y 50 The values were 0.122, 0.111, 0.753, 0.577, 0.775 and 0.613 μ M, respectively. Therefore, (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone shows strong inhibition activity on leukemia HL-60, liver cancer SMMC-7721, liver cancer HepG2, cervical cancer HeLa, prostate cancer PC-3 and human neuroblastoma SH-SY5Y, and has good potential for being developed into antitumor drugs.
In conclusion, the (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone provided by the invention has good transformation or application prospects, and is expected to be used in the production field of antitumor drugs.
It should be noted that, in this document, relational terms such as first and second, and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Furthermore, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or terminal apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or terminal apparatus. Without further limitation, an element defined by the phrases "comprising 8230; \8230;" or "comprising 8230; \8230;" does not exclude the presence of additional elements in a process, method, article, or terminal device that comprises the element. Further, in this document, "greater than," "less than," "more than," and the like are understood to not include the present numbers; the terms "above", "below", "within" and the like are to be understood as including the present number.
Although the embodiments have been described, once they learn of the basic inventive concept, those skilled in the art can make further changes and modifications to these embodiments, so that these embodiments are merely examples of the present invention, and not intended to limit the scope of the invention, and all equivalent structures or equivalent processes that can be used in the present specification, directly or indirectly, in other related fields are encompassed by the present invention.
Claims (6)
1. (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone, having the structure shown in formula (I):
2. a process for preparing (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone, comprising the step of reacting 4-methoxy-3-hydroxybenzoic acid with 2, 4-dimethylphenol in an Eton's reagent to form a benzophenone compound.
3. The method according to claim 2, wherein the Eton reagent is composed of phosphorus pentoxide and methanesulfonic acid, and the molar ratio of the 4-methoxy-3-hydroxybenzoic acid to 2, 4-dimethylphenol is 1.
4. The method of claim 3, comprising the steps of:
adding phosphorus pentoxide into methanesulfonic acid, and stirring at 110 ℃ to dissolve the phosphorus pentoxide to obtain an Eton reagent; cooling the Eton reagent to 90 ℃, adding 4-methoxy-3-hydroxybenzoic acid and 2, 4-dimethylphenol in equal amount, and continuing to react at 90 ℃; after the reaction is finished, pouring the reaction liquid into water, precipitating a sticky substance, and extracting to obtain an initial product; and separating and purifying the primary product by using medium-pressure preparative chromatography to obtain the (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone.
5. The application of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone in preparing antitumor medicine; the tumors comprise leukemia HL-60, lung cancer A-549, liver cancer SMMC-7721, liver cancer HepG2, liver cancer Huh-7, liver cancer SK-HEP-1, liver cancer MHCC97H, liver cancer PLC/PRF/5, breast cancer MCF-7, colon cancer SW480, cervical cancer HeLa, prostate cancer PC-3, breast cancer MDA-MB-231, human neuroblastoma SH-SY5Y and lung cancer Taxol-resistant strain A549/Taxol.
6. An antitumor agent comprising (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone as claimed in claim 1, or a pharmaceutically acceptable salt or ester thereof as an active ingredient.
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| 3种顺铂注射制剂的稳定性研究;肖红军等;《广东药学院学报》;20050225(第01期);第32-33页 * |
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