CN107759558A - A kind of xanthone compound of trifluoromethyl substitution and its preparation method and application - Google Patents
A kind of xanthone compound of trifluoromethyl substitution and its preparation method and application Download PDFInfo
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- CN107759558A CN107759558A CN201710884903.4A CN201710884903A CN107759558A CN 107759558 A CN107759558 A CN 107759558A CN 201710884903 A CN201710884903 A CN 201710884903A CN 107759558 A CN107759558 A CN 107759558A
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- trifluoromethyl
- dihydroxy
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- xanthone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
Abstract
A kind of xanthone compound of trifluoromethyl substitution, is the dihydroxy xanthone of 6 trifluoromethyl 1,3, its structure is shown below：
Description
Technical field
The present invention relates to biochemical field of medicaments, and in particular to a kind of xanthone compound of trifluoromethyl substitution and
Its preparation method and application.
Background technology
Xanthone is also referred to as xanthone, is the secondary metabolite separated from some plants and microorganism at first, contains
There is the precursor structure of dibenzo-gamma-pyrone.Such compound has many important bioactivity, such as anti-hypertension,
Anti- depauperation, antibacterial, antithrombotic and antitumor isoreactivity.These different bioactivity are by different in xanthone female ring
Substituent determines.
Different substituents determines its multiple biological activities in xanthone female ring, and one or more substituent changes
Change can all influence its bioactivity.The xanthone compound with certain bioactivity is obtained, it is necessary to first synthesize oxa-
Anthrone compound, related activity screening is then carried out again.
The content of the invention
Therefore, it is an object of the invention to provide a kind of xanthone chemical combination with certain physiology and pharmacological activity
Thing.
To realize the purpose of the present invention, present invention employs following technical scheme：
A kind of xanthone compound of trifluoromethyl substitution, the compound are 6- Trifluoromethyl-1s, 3- dihydroxy
Xanthone, shown in its structure such as chemical formula (I),
Present invention also offers a kind of preparation method of compound shown in formula I, including by 4- trifluoromethyl -2- hydroxy benzenes
The process that formic acid, phloroglucin, phosphorus pentoxide and Loprazolam are reacted.
Preferably, the mol ratio of 4- trifluoromethyls -2 hydroxybenzoic acid and phloroglucin is 1:1.
Preferably, comprise the following steps：
1) phosphorus pentoxide is dissolved in Loprazolam, prepares the first mixed solution；
2) the first mixed solution is added into 4- trifluoromethyls -2 hydroxybenzoic acid and phloroglucin, carries out ring-closure reaction,
Generate 6- Trifluoromethyl-1s, 3- dihydroxy xanthones；
Preferably, it is further comprising the steps of：
Contain 6- Trifluoromethyl-1s after the completion of 2) reacting, the solution of 3- dihydroxy xanthones is separated out, taken out
Filter, column chromatography for separation, the 6- Trifluoromethyl-1s purified, 3- dihydroxy xanthones.
Preferably, in the step 1), solution temperature is controlled at 105~115 DEG C.
Preferably, in the step 2), reaction temperature control at 88~92 DEG C, reaction time control 18~
22min。
In preparation, the control of temperature is vital.Temperature is too high to make raw material be carbonized and reduce yield, and warm
Degree is too low and can influence the speed of reaction.
Present invention also offers application of the compound shown in formula I in terms of tyrosinase activity is suppressed.
Present invention also offers application of the compound in terms of antineoplastic shown in formula I.
Present invention also offers compound shown in formula I in tyrosinase Metabolism regulation medicine, health products, food, cosmetics
The application of aspect.
Compound 6- Trifluoromethyl-1s shown in formula I provided by the present invention, 3- dihydroxy xanthones, it is a new oxygen
Miscellaneous anthracene ketone compounds, there is obvious antitumor activity and suppress the activity of tyrosinase, available for preparing antineoplastic
With tyrosinase Metabolism regulation medicine, health products, food, cosmetics.The preparation method of compound shown in formula I, operation
Simply, reaction condition is gentle, and yield is high, a large amount of preparations available for compound shown in formula I.
Embodiment
To describe the technology contents of technical scheme, construction feature, the objects and the effects in detail, below in conjunction with specific
Embodiment is explained in detail.
To realize the purpose of the present invention, present invention employs following technical scheme：
A kind of xanthone compound of trifluoromethyl substitution, the compound are 6- Trifluoromethyl-1s, 3- dihydroxy
Xanthone, shown in its structure such as chemical formula (I)：
Present invention also offers a kind of preparation method of compound shown in formula I, including by 4- trifluoromethyl -2- hydroxy benzenes
The process that formic acid, phloroglucin, phosphorus pentoxide and Loprazolam are reacted.
Preferably, the mol ratio of 4- trifluoromethyls -2 hydroxybenzoic acid and phloroglucin is 1:1.
Preferably, comprise the following steps：
1) phosphorus pentoxide is dissolved in Loprazolam, prepares the first mixed solution；
2) the first mixed solution is added into 4- trifluoromethyls -2 hydroxybenzoic acid and phloroglucin, carries out ring-closure reaction,
Generate 6- Trifluoromethyl-1s, 3- dihydroxy xanthones.
Preferably, it is further comprising the steps of：
Contain 6- Trifluoromethyl-1s after the completion of 2) reacting, the solution of 3- dihydroxy xanthones is separated out, taken out
Filter, column chromatography for separation, the 6- Trifluoromethyl-1s purified, 3- dihydroxy xanthones.
Preferably, in the step 1), solution temperature is controlled at 105~115 DEG C.
Preferably, in the step 2), reaction temperature control at 88~92 DEG C, reaction time control 18~
22min。
Present invention also offers application of the compound shown in formula I in terms of tyrosinase activity is suppressed.
Present invention also offers application of the compound in terms of antineoplastic shown in formula I.
Present invention also offers compound shown in formula I in tyrosinase Metabolism regulation medicine, health products, food, cosmetics
The application of aspect.
Compound 6- Trifluoromethyl-1s shown in formula I provided by the present invention, 3- dihydroxy xanthones, it is a new oxygen
Miscellaneous anthracene ketone compounds, there is obvious antitumor activity and suppress the activity of tyrosinase, available for preparing antineoplastic
With tyrosinase Metabolism regulation medicine, health products, food, cosmetics.The preparation method of compound shown in formula I, operation
Simply, reaction condition is gentle, a large amount of preparations available for compound shown in formula I.
For a further understanding of the present invention, with reference to embodiment, the present invention is described in detail.
Embodiment 1：6- Trifluoromethyl-1s, the synthesis of 3- dihydroxy xanthones
By 0.68g phosphorus pentoxides (4.8mmol) and 15mL Loprazolams (MeSO3H 50mL round-bottomed flasks) are sequentially added
In, 110 DEG C are heated to, stirring makes its dissolving, and then reaction solution is down to 90 DEG C, sequentially adds 0.33g 4- trifluoromethyl -2- hydroxyls
Yl benzoic acid (1.6mmol) and 0.20g phloroglucins (1.6 mmol), react about 20min at 90 DEG C.Reaction solution is poured into water
In, solid is separated out, is filtered, naturally dry, the mixed solvent (V of head product ethyl acetate and petroleum etherEthyl acetate：VPetroleum ether=1：
15) 200-300 mesh pressurized silica gel posts are crossed, obtain 0.36g yellow 6- Trifluoromethyl-1s, 3- dihydroxy xanthone solids, yield
For 75.0%.
IR(KBr)vmax 817,837,906,1065,1077,1134,1157,1174,1249,1284,1318, 1352,
1371,1403,1444,1504,1573,1610,1657,3375cm-1；1H NMR(CD3COCD3, 500MHz)δ6.26(1H,d,
J=2.2Hz, H-2), 6.41 (1H, d, J=2.2Hz, H-4), 7.72 (1H, dd, J=1.1,8.3Hz, H-7), 7.82 (1H,
D, J=0.5Hz, H-5), 8.32 (1H, d, J=8.3Hz, H-8), 10.0 (1H, s, HO-3), 12.6 (1H, s, HO-1)；13C
NMR(CD3COCD3,125MHz)δ 95.1,99.4,103.9,116.2,121.1,123.8,125.3,127.9,132.9,
156.3,158.7,164.7, 167.0,180.2；MS-ESI,m/z 295[M-H]；HRMS(ESI)m/z C14H6F3O4(M-H)
Calculated value：295.0224, measured value：295.0226.
Embodiment 2：6- Trifluoromethyl-1s, the antitumor activity test of 3- dihydroxy xanthones
(1) MTS methods detection cytoactive principle
MTS is a kind of brand-new MTT analogs, and full name is the (3- of 3- (4,5-dimethylthiazol-2-yl) -5
Carboxymethoxyphenyl) -2- (4-sulfopheny) -2H-tetrazolium, it is a kind of dyestuff of yellow color.It is living
Succinate dehydrogenase can be metabolized reduction MTS in cell mitochondrial, generate soluble formazans (Formazan) compound, first
The content of Za can be measured with ELIASA at 490nm., formazan growing amounts and viable count are into just under normal conditions
Than, therefore the number of living cells can be deduced according to optical density OD values.
(2) experimental method
1. inoculating cell：Individual cells are made into the nutrient solution (DMEM or RMPI1640) containing 10% hyclone to hang
Liquid, 96 orifice plates are inoculated into every 3000~15000 cells in hole, per the μ l of pore volume 100, attached cell shifts to an earlier date 12~24h inoculations
Culture.
2. add testing compound solution：Compound is dissolved with DMSO, and compound is whole per hole with 40 μM/L concentration primary dcreening operations
The μ l of volume 200, every kind of processing are all provided with 3 multiple holes.
3. develop the color：After 37 DEG C of culture 48h, attached cell abandons nutrient solution in hole, adds the μ l of MTS solution 20 and nutrient solution per hole
100μl；Suspension cell abandons 100 μ l culture supernatants, and 20 μ l MTS solution is added per hole；If 3 blank multiple holes (μ of MTS solution 20
L and the μ l of nutrient solution 100 mixed liquor), continue 2~4h of incubation, absorbance value is determined after the progress that reacts fully.
4. colorimetric：492nm wavelength is selected, multi-function microplate reader (MULTISKAN FC) reads each hole absorbance value, record
As a result, using compound number as abscissa after data processing, cell inhibitory rate is the inhibiting rate that ordinate draws tumour cell
Figure.
5. 9 kinds of tumour cells of the mankind detected are as follows：Leukemia HL-60, T cell leukaemia MT-4, lung cancer A-549, liver
Cancer liver cancer SMMC-7721, liver cancer HepG2, liver cancer Huh-7, colon cancer SW 480, breast cancer MCF-7 and cervical cancer Hela cells are thin
Born of the same parents.
6. for tumour cell of the inhibiting rate more than 50%, then determine IC of the compound to the tumour cell50Value.It is real every time
Test and be all provided with two positive compounds of cis-platinum (DDP) and taxol (Taxol), using concentration as abscissa, cell survival rate is sat to be vertical
Plotting cell growth curve, the IC of compound is calculated using two-point method (Reed and Muench methods)50Value.
By MTS methods, with cis-platinum (DDP) and taxol (Taxol) for positive reference compound, a small amount of embodiment 1 is taken to synthesize
6- Trifluoromethyl-1s, 3- dihydroxy xanthone (abbreviation chemical compounds I) is dissolved in DMSO, is made into 40 μM/L solution,
Then inhibitory activity detection (table 1-3) is carried out to above-mentioned 9 kinds of tumour cells.
Inhibitory activity of the chemical compounds I of table 1 to 5 kinds of tumour cells
Inhibitory activity of the chemical compounds I of table 2 to 4 kinds of tumour cells
IC of the chemical compounds I of table 3 to four kinds of tumour cells50Value
Synthesized 6- Trifluoromethyl-1s are can be seen that from table 1-3,3- dihydroxy xanthone is to human leukemia HL-
60th, the inhibiting rate of human lung cancer A-549, human liver cancer SMMC-7721 and human T cell leukemia MT-4 cells is above 50%, IC50
Value is between 20-39 μM, therefore 6- Trifluoromethyl-1s, 3- dihydroxy xanthone all have to these four human tumor cells
Preferable antitumor activity.
From table 3 it can be seen that 6- Trifluoromethyl-1s, IC of the 3- dihydroxy xanthone to lung cancer A-54950For 29.93 ±
0.47 μM, and cis-platinum is to the IC of lung cancer A-54950For 32.39 ± 0.54 μM, therefore its inhibitory activity ratio to lung cancer A-549 is suitable
Platinum is also strong.
Embodiment 3：6- Trifluoromethyl-1s, 3- dihydroxy xanthone suppress the test of tyrosinase activity
By 6- Trifluoromethyl-1s, 3- dihydroxy xanthones mix with L-Dopa, add tyrosinase (final concentration 25U/
ML) start to react, set 3 repeating holes, while set and be free of 6- Trifluoromethyl-1s, the blank pair of 3- dihydroxy xanthones
OD values, Detection wavelength 490nm are determined according to Kojic Acid positive controls, room temperature, 5min, ELIASA.Junket ammonia is calculated
Phytase activity inhibiting rate.
Inhibitory activity against tyrosinase (%)=(1-sample OD490nm/ experiment contrast hole OD490nm)× 100
Inhibitory action of the chemical compounds I of table 4 to tyrosinase
As can be seen from Table 4,6- Trifluoromethyl-1s, 3- dihydroxy xanthones have suppresses tyrosinase to a certain extent
Effect (inhibiting rate>10%).
In summary, the compound 6- Trifluoromethyl-1s synthesized by the present invention, 3- dihydroxy xanthone is new xanthene
Ketone compounds, have no that the synthesis and bioactivity of document or patent to it are reported.The compound is to leukaemia HL-
60th, T cell leukaemia MT-4, lung cancer A-549, liver cancer SMMC-7721, liver cancer HepG2, liver cancer Huh-7, colon cancer SW 480,
Breast cancer MCF-7 and 9 kinds of tumour cells of s are all inhibited, wherein to human leukemia HL-60, people
4 kinds of lung cancer A-549, human liver cancer SMMC-7721 and human T cell leukemia MT-4 cells tumour cells are respectively provided with high inhibition work
With, it is particularly also stronger than clinically wide variety of cis-platinum to the inhibitory action of lung cancer A-549, it can be applied to antineoplastic
Production.
Meanwhile 6- Trifluoromethyl-1s, 3- dihydroxy xanthone also suppress the effect of tyrosinase to a certain extent,
Therefore it has a good application prospect in terms of tyrosinase Metabolism regulation medicine, health products, food, cosmetics.
It should be noted that herein, such as first and second or the like relational terms are used merely to a reality
Body or operation make a distinction with another entity or operation, and not necessarily require or imply between these entities or operation
Any this actual relation or order be present.Moreover, term " comprising ", "comprising" or its any other variant are intended to
Cover including for nonexcludability, so that process, method, article or terminal device including a series of elements are not only wrapped
Those key elements, but also the other element including being not expressly set out are included, or is also included for this process, method, article
Or the key element that terminal device is intrinsic.In the absence of more restrictions, by sentence " including ... " or " including ... "
The key element of restriction, it is not excluded that also exist in addition in the process including the key element, method, article or terminal device
Key element.In addition, herein, " being more than ", " being less than ", " exceeding " etc. are interpreted as not including this number；" more than ", " following ", " with
It is interior " etc. be interpreted as including this number.
Although the various embodiments described above are described, those skilled in the art once know substantially
Creative concept, then other change and modification can be made to these embodiments, so the foregoing is only the implementation of the present invention
Example, not thereby limit the present invention scope of patent protection, every equivalent structure made using present specification or
Equivalent flow conversion, or other related technical areas are directly or indirectly used in, the patent for being similarly included in the present invention is protected
Within the scope of shield.
Claims (10)
- A kind of 1. xanthone compound of trifluoromethyl substitution, it is characterised in that the compound is 6- Trifluoromethyl-1s, 3- dihydroxy xanthones, shown in its structure such as chemical formula (I)：
- 2. the preparation method of compound described in a kind of claim 1, it is characterised in that including by 4- trifluoromethyl -2- hydroxy benzenes The process that formic acid, phloroglucin, phosphorus pentoxide and Loprazolam are reacted.
- 3. preparation method according to claim 2, it is characterised in that 4- trifluoromethyls -2 hydroxybenzoic acid and isophthalic three The mol ratio of phenol is 1:1.
- 4. preparation method according to claim 2, it is characterised in that comprise the following steps：1) phosphorus pentoxide is dissolved in Loprazolam, prepares the first mixed solution；2) the first mixed solution is added into 4- trifluoromethyls -2 hydroxybenzoic acid and phloroglucin, carries out ring-closure reaction, generate 6- Trifluoromethyl-1,3- dihydroxy xanthones.
- 5. preparation method according to claim 4, it is characterised in that further comprising the steps of：Contain 6- Trifluoromethyl-1s after the completion of 2) reacting, the solution of 3- dihydroxy xanthones is separated out, filtered, post layer Analysis separation, the 6- Trifluoromethyl-1s purified, 3- dihydroxy xanthones.
- 6. preparation method according to claim 4, it is characterised in that in the step 1), solution temperature is controlled 105 ~115 DEG C.
- 7. preparation method according to claim 4, it is characterised in that in the step 2), reaction temperature is controlled 88 ~92 DEG C, the reaction time is controlled in 18~22min.
- 8. the xanthone compound that trifluoromethyl described in claim 1 substitutes answering in terms of tyrosinase activity is suppressed With.
- 9. application of the xanthone compound that trifluoromethyl described in claim 1 substitutes in terms of antineoplastic.
- 10. the xanthone compound that trifluoromethyl described in claim 1 substitutes is in tyrosinase Metabolism regulation medicine, health care Application in terms of product, food, cosmetics.
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| CN107698550A (en) * | 2017-09-26 | 2018-02-16 | 莆田学院 | A kind of xanthone compound of 2,4 difluorophenyl substitution and its preparation method and application |
| CN108619132A (en) * | 2018-06-29 | 2018-10-09 | 莆田学院 | Application of -1,3 dihydroxy xanthone of 7- nitros in terms of preparing antitumor drug |
| CN108689983A (en) * | 2018-07-05 | 2018-10-23 | 莆田学院 | Tri- chloro- 1,3- dihydroxy xanthone compounds of 5,7,8-, preparation method and application |
| CN108752306A (en) * | 2018-07-19 | 2018-11-06 | 莆田学院 | Fluoro- 1,3- dihydroxy xanthones of 6- and its preparation method and application |
| CN108938619A (en) * | 2018-06-29 | 2018-12-07 | 莆田学院 | 7-(2,4- difluorophenyl) the application of -1,3- dihydroxy xanthone in terms of preparing anti-tumor drug |
| CN108997300A (en) * | 2018-07-19 | 2018-12-14 | 莆田学院 | Fluoro- 1,3- dihydroxy xanthone of 7,8- bis- and its preparation method and application |
| CN112608305A (en) * | 2020-12-21 | 2021-04-06 | 浙江工业大学 | Mangiferin derivative, preparation method thereof and application thereof in whitening products |
| CN113105428A (en) * | 2021-03-10 | 2021-07-13 | 宁波大学 | Xanthone compound and preparation method and application thereof |
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| CN107698550A (en) * | 2017-09-26 | 2018-02-16 | 莆田学院 | A kind of xanthone compound of 2,4 difluorophenyl substitution and its preparation method and application |
| CN108619132B (en) * | 2018-06-29 | 2020-07-17 | 莆田学院 | Application of 7-nitro-1, 3 dihydroxy xanthone in preparation of antitumor drugs |
| CN108619132A (en) * | 2018-06-29 | 2018-10-09 | 莆田学院 | Application of -1,3 dihydroxy xanthone of 7- nitros in terms of preparing antitumor drug |
| CN108938619A (en) * | 2018-06-29 | 2018-12-07 | 莆田学院 | 7-(2,4- difluorophenyl) the application of -1,3- dihydroxy xanthone in terms of preparing anti-tumor drug |
| CN108938619B (en) * | 2018-06-29 | 2020-02-28 | 莆田学院 | Application of 7- (2, 4-difluorophenyl) -1, 3-dihydroxyxanthone in preparation of antitumor drugs |
| CN108689983A (en) * | 2018-07-05 | 2018-10-23 | 莆田学院 | Tri- chloro- 1,3- dihydroxy xanthone compounds of 5,7,8-, preparation method and application |
| CN108689983B (en) * | 2018-07-05 | 2021-09-03 | 莆田学院 | 5,7, 8-trichloro-1, 3-dihydroxy xanthone compound, preparation method and application |
| CN108752306A (en) * | 2018-07-19 | 2018-11-06 | 莆田学院 | Fluoro- 1,3- dihydroxy xanthones of 6- and its preparation method and application |
| CN108997300B (en) * | 2018-07-19 | 2021-09-03 | 莆田学院 | 7, 8-difluoro-1, 3-dihydroxy xanthone and preparation method and application thereof |
| CN108997300A (en) * | 2018-07-19 | 2018-12-14 | 莆田学院 | Fluoro- 1,3- dihydroxy xanthone of 7,8- bis- and its preparation method and application |
| CN108752306B (en) * | 2018-07-19 | 2021-09-17 | 莆田学院 | 6-fluoro-1, 3-dihydroxy xanthone and preparation method and application thereof |
| CN112608305A (en) * | 2020-12-21 | 2021-04-06 | 浙江工业大学 | Mangiferin derivative, preparation method thereof and application thereof in whitening products |
| CN113105428A (en) * | 2021-03-10 | 2021-07-13 | 宁波大学 | Xanthone compound and preparation method and application thereof |
| CN113105428B (en) * | 2021-03-10 | 2022-05-17 | 宁波大学 | Xanthone compound and preparation method and application thereof |
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