CN111333495A - (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
- Publication number
- CN111333495A CN111333495A CN202010311435.3A CN202010311435A CN111333495A CN 111333495 A CN111333495 A CN 111333495A CN 202010311435 A CN202010311435 A CN 202010311435A CN 111333495 A CN111333495 A CN 111333495A
- Authority
- CN
- China
- Prior art keywords
- hydroxyphenyl
- methoxy
- cancer
- dimethyl
- methanone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a novel 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.
The (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 preparing (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone, comprising reacting 4-methoxy-3-hydroxybenzoic acid with 2, 4-dimethylphenol in an eaton's reagent to form a benzophenone compound.
Further, the Eton 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: 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 sticky substance, and extracting to obtain a primary product; the primary product is separated and 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, the invention provides an application of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone in preparing an anti-tumor medicament.
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 conditions and high 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, 4.1mmol) and methanesulfonic acid (10mL) were sequentially added to a 25mL round-bottomed flask, heated to 110 ℃ and stirred to dissolve, the reaction solution was cooled to 90 ℃ and 4-methoxy-3-hydroxybenzoic acid (0.34g, 2.0mmol) and 2, 4-dimethylphenol (0.26mL, 2.0mmol) were sequentially added, and the reaction was continued at 90 ℃ for 0.5 h. 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 percent and the mp is 101-. A mixed solvent of ethyl acetate and petroleum ether was used as an eluent for medium pressure preparative chromatography.
IR(KBr)vmax552,628,761,790,876,1020,1134,1187,1218,1278, 1361,1423,1510,1564,1609,1728,2852,2918,2955,2976,3013,3288 cm-1；1H NMR (500MHz, acetone-d6)δ2.22(s,6H,2CH3-),3.95(s,3H,CH3O-), 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’)；13C NMR (125MHz, 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. Since the formazan production amount is generally proportional to the number of viable cells, the number of viable cells can be estimated from the optical density OD value.
(2) Experimental methods
① inoculating cells, preparing single cell suspension with culture solution (DMEM or RMPI1640) containing 10% fetal calf serum, inoculating 3000-15000 cells per well into 96-well plate, each well volume being 100 μ l, inoculating adherent cells 12-24h in advance, and culturing.
② adding test compound solution, dissolving the compound with dimethyl sulfoxide (DMSO), sieving the compound at 40 μ M concentration, setting 3 multiple wells for each treatment (mixed solution of 20 μ l MTS solution and 100 μ l culture solution) with final volume of 200 μ l each, incubating for 2-4h, and determining light absorption value after reaction is fully performed.
③ color development, after culturing for 48h at 37 ℃, removing the culture solution in each hole of the adherent cells, adding 20 mul of MTS solution and 100 mul of culture solution in each hole, removing 100 mul of culture supernatant of the suspended cells, adding 20 mul of MTS solution in each hole, arranging 3 blank duplicate holes (mixed solution of 20 mul of MTS solution and 100 mul of culture solution), continuing incubation for 2-4h, and measuring the light absorption value after the reaction is fully performed.
④ colorimetric, selecting 492nm wavelength, reading the light absorption value of each well with multifunctional enzyme labeling instrument (MULTISKAN FC), recording the result, and plotting the inhibition percentage of tumor cells with the compound number as abscissa and the cell inhibition percentage as ordinate after data processing.
⑤ for tumor cells with a percentage of inhibition of more than 50%, rescreening at concentrations of 40. mu.M, 8. mu.M, 1.6. mu.M, 0.32. mu.M, 0.064. mu.M, and re-determining the IC of the compound on the tumor cells50The 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)50The value is obtained.
For convenience of description, (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone is referred to as compound 1 for short. 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 against 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 cells50Value of
TABLE 5 IC of Compound 1 on 2 hepatoma cells50Value of
TABLE 6 IC of Compound 1 on 5 additional cancer cells50Value of
As can be seen from tables 1-6, Compound 1 is resistant to leukemia HL-60, lung cancer A-549, liver cancer SMMC-7721, breast cancer MCF-7, colon cancer SW480, liver cancer (HepG2 and Huh-7), cervical cancer HeLa, prostate cancer PC-3, breast cancer MDA-MB-231, human neuroblastoma SH-SY5Y and lung cancer taxolThe percent inhibition of the drug strain A549/Taxol exceeds 50 percent, and the IC of the drug strain A549/Taxol is50The 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, IC of compound 1 against 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/Taxol50The values are respectively 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, and the positive control drug cisplatin is used for treating 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 IC of lung cancer Taxol-resistant strain A549/Taxol50The 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. mu.M, respectively. Thus, IC of Compound 1 on the 11 cancer cells described above50The 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-772150The 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 the classical antitumor drug taxol.
It is particularly emphasized that compound 1 has IC effect on leukemia HL-60, liver cancer SMMC-7721, liver cancer HepG2, cervical cancer HeLa, prostate cancer PC-3 and human neuroblastoma SH-SY5Y50The 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 modification or application prospect, and is expected to be used in the production field of antitumor drugs.
It is noted that, herein, relational terms such as first and second, and the like may be 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. Also, 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 … …" or "comprising … …" does not exclude the presence of additional elements in a process, method, article, or terminal 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 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 (7)
- (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone, having the structure shown in formula (I):。
- 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 Eton's reagent to form a benzophenone compound.
- 3. The method of claim 2, wherein the Eton's reagent is composed of phosphorus pentoxide and methanesulfonic acid, and the molar ratio of 4-methoxy-3-hydroxybenzoic acid to 2, 4-dimethylphenol is 1: 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 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 liquid into water, separating out a sticky substance, and extracting to obtain a primary product; and separating and purifying the primary product by medium-pressure preparative chromatography to obtain (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone.
- Application of (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) methanone in preparation of antitumor drugs.
- 6. The use of claim 5, wherein the tumor comprises 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 paclitaxel-resistant strain A549/Taxol.
- 7. 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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010311435.3A CN111333495B (en) | 2020-04-20 | 2020-04-20 | (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010311435.3A CN111333495B (en) | 2020-04-20 | 2020-04-20 | (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111333495A true CN111333495A (en) | 2020-06-26 |
| CN111333495B CN111333495B (en) | 2023-01-31 |
Family
ID=71179148
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010311435.3A Active CN111333495B (en) | 2020-04-20 | 2020-04-20 | (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111333495B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111943830A (en) * | 2020-08-20 | 2020-11-17 | 莆田学院 | Novel benzophenone compound and preparation method and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030220304A1 (en) * | 2000-04-27 | 2003-11-27 | Pettit George R. | Hydroxyphenstatin and the prodrugs thereof |
| CN101123954A (en) * | 2005-02-21 | 2008-02-13 | 协和发酵工业株式会社 | Anti-tumor agent |
| CN103910643A (en) * | 2014-04-23 | 2014-07-09 | 温州大学 | Anti-cancer activity ketone derivative as well as synthetic method and application thereof |
| CN106138018A (en) * | 2015-04-02 | 2016-11-23 | 广州洁成生物科技有限公司 | Dihydroxy benaophenonel application in preparing antiviral and antitumor drug |
| CN109879921A (en) * | 2019-03-26 | 2019-06-14 | 安徽中医药大学 | Compound with anti-tumor activity separated from rhizoma anemarrhenae and preparation method thereof |
| CN110590739A (en) * | 2019-09-20 | 2019-12-20 | 中国药科大学 | Preparation method of erlotinib |
| CN110668936A (en) * | 2019-10-21 | 2020-01-10 | 扬州工业职业技术学院 | Method for ultrasonically extracting benzophenone compounds from aquilaria sinensis leaves |
-
2020
- 2020-04-20 CN CN202010311435.3A patent/CN111333495B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030220304A1 (en) * | 2000-04-27 | 2003-11-27 | Pettit George R. | Hydroxyphenstatin and the prodrugs thereof |
| CN101123954A (en) * | 2005-02-21 | 2008-02-13 | 协和发酵工业株式会社 | Anti-tumor agent |
| CN103910643A (en) * | 2014-04-23 | 2014-07-09 | 温州大学 | Anti-cancer activity ketone derivative as well as synthetic method and application thereof |
| CN106138018A (en) * | 2015-04-02 | 2016-11-23 | 广州洁成生物科技有限公司 | Dihydroxy benaophenonel application in preparing antiviral and antitumor drug |
| CN109879921A (en) * | 2019-03-26 | 2019-06-14 | 安徽中医药大学 | Compound with anti-tumor activity separated from rhizoma anemarrhenae and preparation method thereof |
| CN110590739A (en) * | 2019-09-20 | 2019-12-20 | 中国药科大学 | Preparation method of erlotinib |
| CN110668936A (en) * | 2019-10-21 | 2020-01-10 | 扬州工业职业技术学院 | Method for ultrasonically extracting benzophenone compounds from aquilaria sinensis leaves |
Non-Patent Citations (6)
| Title |
|---|
| KATSUYA MAEYAMA等: "P2O5–MsOH Mediated Regioselective Diaroylation of 2,20-Dimethoxy-1,10-binaphthyl", 《SYNTHETIC COMMUNICATIONS》 * |
| 于湘莉等: "紫杉醇在水环境中的降解动力学研究", 《上海交通大学学报(农业科学版)》 * |
| 刘洋等: "4-(4-羟基-3-甲氧基苯甲基)姜黄素合成及其抗肿瘤活性", 《中国医院药学杂志》 * |
| 周北斗等: "3-甲氧基-1-羟基氧杂蒽酮的合成及其生物活性探究", 《莆田学院学报》 * |
| 李斌等: "顺铂稳定性实验观察", 《甘肃医药》 * |
| 肖红军等: "3种顺铂注射制剂的稳定性研究", 《广东药学院学报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111943830A (en) * | 2020-08-20 | 2020-11-17 | 莆田学院 | Novel benzophenone compound and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111333495B (en) | 2023-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107759558B (en) | Trifluoromethyl substituted xanthone compound and preparation method and application thereof | |
| CN113045399B (en) | Chalcone derivatives and uses thereof | |
| Kowalski et al. | Ferrocenyl derivatives of pterocarpene and coumestan: Synthesis, structure and anticancer activity studies | |
| CN111333495B (en) | (4-methoxy-3-hydroxyphenyl) (3, 5-dimethyl-2-hydroxyphenyl) ketone, and preparation method and application thereof | |
| CN114478502B (en) | Coumarin compound and synthesis method thereof | |
| CN111303189A (en) | Propenone derivative of rufloxacin, and preparation method and application thereof | |
| CN111303190A (en) | Propenone derivative for removing N-methylrufloxacin and preparation method and application thereof | |
| CN107827934B (en) | Tetravalent platinum complex with anticancer activity, preparation method and application | |
| CN114292241B (en) | Cannabidiol-2-dioxopiperazinoate and application thereof | |
| CN111004145B (en) | Chiral optical amide substituted alpha, beta-diamino acid derivative and preparation method and application thereof | |
| CN109180583B (en) | Synthesis and application of naphthalimide derivative containing heterocyclic sulfone group and N-oxide | |
| CN108373488B (en) | Catalpol 6-caffeic acid ester derivative and preparation method and application thereof | |
| CN111196791A (en) | Chiral gamma-butyrolactone derivative and synthesis method and application thereof | |
| CN111892486A (en) | Hydroxyl-substituted benzophenone compound and preparation method and application thereof | |
| CN108752306B (en) | 6-fluoro-1, 3-dihydroxy xanthone and preparation method and application thereof | |
| CN108689983B (en) | 5,7, 8-trichloro-1, 3-dihydroxy xanthone compound, preparation method and application | |
| CN108997300B (en) | 7, 8-difluoro-1, 3-dihydroxy xanthone and preparation method and application thereof | |
| CN115181112B (en) | Synthesis and anti-tumor application of 6-bromo-cycloicaritin chromane 3, 4-diketone derivative | |
| CN112824396A (en) | N-acetyl lomefloxacin allyl ketone derivative and preparation method and application thereof | |
| CN105777773B (en) | Thiophene [2,3 b] quinoline and its synthetic method and application | |
| CN110183320B (en) | Polyene diketone antitumor compound | |
| CN111943830B (en) | Novel benzophenone compound and preparation method and application thereof | |
| CN115043720B (en) | Novel alpha-methyl chalcone compound and preparation method and application thereof | |
| CN111018780B (en) | N-carbonyl-9, 10-dihydroacridine compound and application thereof | |
| CN112062743B (en) | Resveratrol derivative and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |