CN103755692B - A kind of compound and preparation method thereof, purposes, pharmaceutical composition and preparation - Google Patents
A kind of compound and preparation method thereof, purposes, pharmaceutical composition and preparation Download PDFInfo
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- CN103755692B CN103755692B CN201410043320.5A CN201410043320A CN103755692B CN 103755692 B CN103755692 B CN 103755692B CN 201410043320 A CN201410043320 A CN 201410043320A CN 103755692 B CN103755692 B CN 103755692B
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- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
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Abstract
The present invention relates to pharmaceutical field, relate to a kind of compound and preparation method thereof, purposes, pharmaceutical composition and preparation specifically.Compound of the present invention is compound shown in formula I, and wherein, Ac is ethanoyl.Compound shown in formula I of the present invention is new xanthone compounds, there is the effect of serum uric acid level of obvious anti-tumor activity, hypoglycemic activity and reduction hyperuricemia mouse, can be used for preparing antitumor drug, prevention or treatment diabetes medicament or having regulating blood uric acid function medicament.Shown in formula I, the preparation method of compound, simple to operate, and raw material is easy to get, and reaction conditions is gentle, can be used for a large amount of preparations of compound shown in formula I.
Description
Technical field
The present invention relates to field of pharmacology, relate to a kind of compound and preparation method thereof, purposes, pharmaceutical composition and preparation specifically.
Background technology
Xanthone is a kind of organic compound, can be obtained through heating by salol.Nineteen thirty-nine, xanthone starts to be used to manufacture sterilant, is used as ovicide (ovicide) and the larvacide (larvicide) of carpocapsa pononella (codlingmoth) ovum afterwards.Xanthone is also used to prepare flavol.Xanthone reduzate is xanthgdrol, for the identification of aliphatic amide type, amino formate compounds, is also used as the blocking group of acyloxy.
There is the derivative of numerous xanthone in occurring in nature, as mangostin etc., they are referred to as xanthone compounds.This compounds is mainly present in some more high plant species, as in the plants such as Gentianaceae, Moraceae, guttiferae, Polygalaceae, pulse family and fungi and lichens.The xanthone compounds of different structure, often has different pharmacological actions or level of activity.At present, the mankind find, isolated more than 200 kind of xanthone compounds, pharmacological research shows, has found that xanthone compounds has pharmacologically active widely, comprises diuresis, antibacterial, antiviral, cardiac stimulant, antidepressant, tuberculosis, anticancer, anti-liver poison isoreactivity.On the basis of natural drug, utilizing chemical means to synthesize new compound, is the effective way that the world today finds new drug.Therefore, in recent years by the method for organic synthesis, synthesis has certain physiology and pharmacologically active xanthone compounds, becomes the focus of people's research.
Summary of the invention
In view of this, the object of the invention is to provide and a kind ofly has certain physiology and pharmacologically active xanthone compounds.
For realizing object of the present invention, the present invention adopts following technical scheme:
Compound shown in a kind of formula I,
Wherein, Ac is ethanoyl.
Present invention also offers the preparation method of compound shown in a kind of formula I, under catalyst action, 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide react obtained in a solvent.
Preferably, the mol ratio of described 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide is 1.0:5.0 ~ 1.0:10.0.
Preferably, described catalyzer is acetate.
Preferably, described acetate is sodium acetate or potassium acetate.
Preferably, described solvent is Glacial acetic acid.
Preferably, described temperature of reaction is 40 DEG C ~ 70 DEG C.
Preferably, the described reaction times is 2h ~ 5h.
Present invention also offers compound shown in formula I preparing antitumor drug, prevention or treatment diabetes medicament or there is the application regulated in blood uric acid function medicament.
Present invention also offers a kind of pharmaceutical composition, compound shown in formula I described in the claim 1 comprising treatment significant quantity.
Present invention also offers a kind of pharmaceutical preparation, comprise treatment significant quantity formula I shown in compound and pharmaceutically acceptable auxiliary material.
Preferably, described pharmaceutical preparation is tablet, capsule, injection liquid or lyophilized injectable powder.
Compound shown in formula I of the present invention is a new xanthone compounds, there is the effect of serum uric acid level of obvious anti-tumor activity, hypoglycemic activity and reduction hyperuricemia mouse, can be used for preparing antitumor drug, prevention or treatment diabetes medicament or having regulating blood uric acid function medicament.Shown in formula I, the preparation method of compound, simple to operate, and raw material is easy to get, and reaction conditions is gentle, can be used for a large amount of preparations of compound shown in formula I.
Embodiment
The embodiment of the invention discloses a kind of compound and preparation method thereof, purposes, pharmaceutical composition and preparation.Those skilled in the art can use for reference present disclosure, and suitable improving technique parameter realizes.Special needs to be pointed out is, all similar replacements and change apparent to those skilled in the art, they are all deemed to be included in the present invention.Product of the present invention, method and application are described by preferred embodiment, related personnel obviously can not depart from content of the present invention, spirit and scope product as herein described, method and application are changed or suitably change with combination, realize and apply the technology of the present invention.
For realizing object of the present invention, the present invention adopts following technical scheme:
The present invention utilizes modern chemistry synthesis and structure transformation means to obtain a kind of new xanthone compounds, and it has structure shown in formula I,
Wherein, Ac is ethanoyl.
Present invention also offers the preparation method of compound shown in a kind of formula I, under catalyst action, 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide react obtained in a solvent.Reaction formula is as follows:
Wherein, Ac is ethanoyl.
Wherein, in the preparation method of compound shown in formula I of the present invention, described 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, also known as 1,6, the two benzene pyrrone-2-C-β-D-glucopyranoside of 7-trihydroxy--3-methoxyl group, its structural formula, such as formula shown in II, can prepare according to method disclosed in existing document or patent.
As preferably, in the preparation method of compound shown in formula I of the present invention, the mol ratio of described 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide is 1.0:5.0 ~ 1.0:10.0.
In some embodiments, in the preparation method of compound shown in formula I of the present invention, described catalyzer is acetate.Described catalyzer is sodium acetate in certain embodiments.Described in other specific embodiments, catalyzer is potassium acetate.
In some embodiments, in the preparation method of compound shown in formula I of the present invention, described solvent is Glacial acetic acid.
As preferably, in the preparation method of compound shown in formula I of the present invention, described 1, the mol ratio of 6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, acetate, Glacial acetic acid is 1.0:(5.0 ~ 10.0): (2.0 ~ 6.0): (10.0 ~ 15.0).The mol ratio of described 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, sodium acetate, Glacial acetic acid is 1.0:8.0:4.0:12.0 in certain embodiments.The mol ratio of described 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, sodium acetate, Glacial acetic acid is 1.0:10.0:3.0:15.0 in certain embodiments.Described in other specific embodiments, the mol ratio of 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide, potassium acetate, Glacial acetic acid is 1.0:5.0:2.0:10.0.
The temperature of reaction of preparation method of the present invention is generally 40 DEG C ~ 70 DEG C.In certain embodiments, described temperature of reaction is 60 DEG C; In certain embodiments, described temperature of reaction is 40 DEG C; In other specific embodiments, described temperature of reaction is 70 DEG C.
The reaction times of preparation method of the present invention is generally 2h ~ 5h.In some embodiments, the described reaction times is 3h ~ 4h.In certain embodiments, the described reaction times is 3h; In certain embodiments, the described reaction times is 4h; In other specific embodiments, the described reaction times is 4h.
Further, need to carry out purifying to reaction solution after preparation method's reaction of the present invention terminates, be separated and obtain compound shown in formula I.Described purification process concrete grammar stirs for the 20mL that adds water, and with petroleum ether extraction reaction solution 2 times (2 × 50mL), collect petroleum ether extraction liquid, vacuum reclaims sherwood oil, crystallization and get final product.
Through mass spectrum, nuclear magnetic resonance spectroscopy, determine that the xanthone compounds prepared is the tetra-acetylated glucopyranoside of 1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-.
MTT colorimetry is the method that in vitroanticancer drug screening is conventional, has simply, fast, accurately, does not relate to and use radioelement and the advantage such as result is consistent with Isotope inc orporation, widely use the common method as in vitroanticancer drug screening.In a specific embodiment, the present invention with Hela, A-549, Bel-7402 and HL-60 tumour cell of logarithmic phase for research object, anti-tumor activity experiment is carried out by mtt assay, find that shown in formula I of the present invention, compound has obvious restraining effect to Hela, A-549, Bel-7402 and HL-60 growth of tumour cell, show that shown in formula I of the present invention, compound has obvious anti-tumor activity.Therefore the invention provides compound shown in formula I and prepare the application in antitumor drug.
In a specific embodiment, by tetraoxypyrimidine hyperglycemia mouse blood sugar impact test, find that compound shown in formula I of the present invention has obvious hypoglycemic activity to tetraoxypyrimidine hyperglycemia mouse.Therefore the invention provides the application of compound shown in formula I in preparation prevention or treatment diabetes medicament.
In another embodiment, the present invention, by the impact test of the acute hyperuricemia mouse uric acid on Oteracil Potassium induction, proves that compound shown in formula I of the present invention significantly can reduce the serum uric acid level of hyperuricemia mouse.Therefore present invention also offers compound shown in formula I and there is in preparation the application regulated in blood uric acid function medicament.
Present invention also offers a kind of pharmaceutical composition, comprise treatment significant quantity formula I of the present invention shown in compound.
Present invention also offers a kind of pharmaceutical preparation, comprise treatment significant quantity formula I of the present invention shown in compound and pharmaceutically acceptable auxiliary material.Compound shown in described formula I can directly or indirectly be added pharmaceutically acceptable various conventional auxiliary materials required when preparing different dosage form by those skilled in the art, as weighting agent, disintegrating agent, lubricant, tackiness agent etc., with traditional drug formulations method, make common dosage forms as tablet, capsule, injection liquid, oral liquid, granule, pill, powder and pill etc.Wherein, weighting agent as starch, lactose, sucrose, glucose, N.F,USP MANNITOL and silicic acid; Disintegrating agent as agar, calcium carbonate, potato starch or tapioca (flour), Lalgine, some silicate and sodium carbonate, low-substituted hydroxypropyl cellulose; Lubricant as talcum powder, calcium stearate, Magnesium Stearate, solid polyethylene glycol, Sulfuric acid,monododecyl ester, sodium salt; Tackiness agent as carboxymethyl cellulose, alginate, gelatin, Povidone, sucrose and gum arabic.
In some embodiments, pharmaceutical preparation of the present invention is tablet, capsule, injection liquid or lyophilized injectable powder.
Compound shown in formula I of the present invention is new xanthone compounds, there is the effect of serum uric acid level of obvious anti-tumor activity, hypoglycemic activity and reduction hyperuricemia mouse, can be used for preparing antitumor drug, prevention or treatment diabetes medicament or having regulating blood uric acid function medicament.Shown in formula I, the preparation method of compound, simple to operate, and raw material is easy to get, and reaction conditions is gentle, can be used for a large amount of preparations of compound shown in formula I.
In order to understand the present invention further, below in conjunction with embodiment, the present invention is described in detail.
The preparation of the tetra-acetylated glucopyranoside of embodiment 1:1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-
In 1000mL reaction flask, add 43.6g (0.1mol) 1, 6, 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, 81.6g (0.8mol) diacetyl oxide, 32.8g (0.4mol) sodium acetate, 72.0g (1.2mol) Glacial acetic acid, in 60 DEG C of stirring reaction 3h, add water 200mL, with petroleum ether extraction 2 times (2 × 300mL), collect petroleum ether extraction liquid, vacuum reclaims sherwood oil, crystallization, obtain 1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside 65.3g of 7-diacetoxy mountain ketone-2-C-β-D-, yield 94.9%.Spectral data:
1hNMR (CDCl
3) δ: 13.09(1H ,-OH), 7.73 (1H, Ar-H), 6.72 (1H, Ar-H), 6.47 (1H, Ar-H), 6.34 (1H, Ar-H), 3.97 (3H ,-OCH
3), 5.44-3.90(7H, glc-H); PositiveFABMS:m/z689 [M+H]
+; PositiveHRFABMSm/z689.1733 [M+H]
+, Calcd.forC
32h
33o
17, 689.1731.
The preparation of the tetra-acetylated glucopyranoside of embodiment 2:1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-
In 1000mL reaction flask, add 43.6g (0.1mol) 1, 6, 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, 102.0g (1.0mol) diacetyl oxide, 24.6g (0.3mol) sodium acetate, 90.0g (1.5mol) Glacial acetic acid, in 40 DEG C of stirring reaction 4h, add water 200mL, with petroleum ether extraction 2 times (2 × 300mL), collect petroleum ether extraction liquid, vacuum reclaims sherwood oil, crystallization, obtain 1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside 65.5g of 7-diacetoxy mountain ketone-2-C-β-D-, yield 95.2%.Spectral data is with embodiment 1.
The preparation of the tetra-acetylated glucopyranoside of embodiment 3:1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-
In 1000mL reaction flask, add 43.6g (0.1mol) 1, 6, 7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside, 51.0g (0.5mol) diacetyl oxide, 19.6g (0.2mol) potassium acetate, 60.0g (1.0mol) Glacial acetic acid, in 40 DEG C of stirring reaction 4h, add water 200mL, with petroleum ether extraction 2 times (2 × 300mL), collect petroleum ether extraction liquid, vacuum reclaims sherwood oil, crystallization, obtain 1-hydroxy-3-methoxy-6, the tetra-acetylated glucopyranoside 63.1g of 7-diacetoxy mountain ketone-2-C-β-D-, yield 91.7%.Spectral data is with embodiment 1.
Embodiment 4: anti-tumor activity is tested
Adopt mtt assay, by different tumour generating rate, the Hela of logarithmic phase, A-549 will be in, Bel-7402, HL-60 tumour cell is inoculated in 96 well culture plates respectively, every hole 90 μ L, adds compound shown in formula I (prepared by embodiment 1), reference substance (1 respectively after cultivating 24h, 6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside), every hole 10 μ L, each concentration of each cell strain all establishes three repeating holes.Then at 37 DEG C, 5%CO
2cultivate 48h under condition, add 5mg/LMTT liquid, every hole 20 μ L, after continuing to cultivate 4h, add the every hole 50 μ L of three liquid (10%SDS-5% isopropylcarbinol-0.01mol/LHCl) in CO
2spend the night in incubator, then under 570nm, measure OD value by microplate reader.Calculate analyte to the inhibiting rate of growth of tumour cell, adopt Logit method to calculate half amount of suppression IC
50value, the results are shown in Table 1.
Table 1 anti-tumor activity experimental result
From table 1, shown in formula I of the present invention, compound has obvious inhibition to Hela, A-549, Bel-7402 and HL-60 growth of tumour cell, shows that shown in formula I of the present invention, compound has obvious anti-tumor activity.
Embodiment 5: hypoglycemic activity is tested
Get normal mouse, tail vein injection tetraoxypyrimidine (80mg/kg), serum level of glucose is measured after 72h, select blood glucose value more than 16mmol/L mouse as supplying examination mouse, be divided into Normal group, tetraoxypyrimidine group, drug control group (1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside), compound group (prepared by embodiment 1) shown in formula I.Every day gastric infusion 1 time, Normal group, tetraoxypyrimidine group give equal-volume distilled water, continuous 7 days.1h after last administration, gets blood from mouse orbit venous plexus, uses kit measurement glucose level after centrifuging and taking serum.The results are shown in Table 2.
Table 2 is on the impact (x ± s, n=10) of alloxan diabetes mouse blood sugar
From table 2 result, after giving compound shown in formula I of the present invention, tetraoxypyrimidine hyperglycemia mouse blood sugar obviously reduces, and shows that shown in formula I of the present invention, compound has obvious hypoglycemic activity.
Embodiment 6: the impact of hyperuricemia mouse is tested
Get 40 Kunming mouses and be divided into 4 groups at random: Normal group, hyperuricemia model group, drug control group (1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside), compound group (prepared by embodiment 1) shown in formula I.Test-compound 0.5% Xylo-Mucine (0.5%CMC-Na) is mixed with suspension, and gavage gives, every day 2 times, continuous 5 times.Mouse is 2h abdominal injection 400mg/kg Oxonic Acid sylvite before blood sampling, suppress uricase activity, cause hyperuricemia mouse (PathogenesisofGout.AnnalsofInternalMedicine.2005,143 (7): 499-516.), Normal group then injects equal-volume 0.5%CMC-Na solution, after injection 1h, gavage carries out last administration, extract eyeball after 2h and get blood, the centrifugal 5min of 3000rpm, get serum, adopt enzymic colorimetric (Zhongsheng Beikong Biological Science & Technology Co., Ltd.'s test kit) to measure serum uric acid level, the results are shown in Table 3.
Table 3 is on the impact (x ± s, n=10) of hyperuricemia mouse
From table 3 result, after abdominal injection Oteracil Potassium, animal serum uric acid level significantly raises, hints model success.After gastric infusion 5 times, shown in formula I, compound group serum uric acid level is starkly lower than hyperuricemia model group, show that compound shown in formula I of the present invention can reduce the acute hyperuricemia mice serum uric acid level of Oteracil Potassium induction, there is the effect significantly suppressing hyperuricemia mice serum uric acid level.
Embodiment 7: containing the tablet of compound shown in formula I
The tablet formulation composition of the compound (the tetra-acetylated glucopyranoside of 1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-) that every sheet is prepared containing 30mg embodiment 1:
Preparation method: after compound, starch, Microcrystalline Cellulose, sodium starch glycolate and Magnesium Stearate mixing prepared by embodiment 1 on tabletting machine compressing tablet, obtain the tablet of compound that every sheet is prepared containing 30mg embodiment 1, the heavy 300mg of every sheet.
Embodiment 8: containing the capsule of compound shown in formula I
The capsule formula composition of the compound (the tetra-acetylated glucopyranoside of 1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-) that every capsule is prepared containing 30mg embodiment 1:
Preparation method: compound embodiment 1 prepared, dry starch, hydroxyl Starch Sodium and Magnesium Stearate mix, and be packed in hard gelatin capsule, obtain final product with the amount of 30mg.
Embodiment 9: containing the injection liquid of compound shown in formula I
Often prop up the injection liquid formula composition of the compound (the tetra-acetylated glucopyranoside of 1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-) prepared containing 15mg embodiment 1:
Preparation method: compound prepared by embodiment 1 is added ethanol stirring and dissolving, with N.F,USP MANNITOL and appropriate water for injection, stir, add 0.1% pin activated carbon, absorption, filter decarburization, mend and inject water to specified amount, millipore filtration membrane filtration, embedding is propped up by 1mL/, 100 DEG C of moist heat sterilizations 20 minutes, qualified through lamp inspection, to obtain final product.
Embodiment 10: containing the lyophilized injectable powder of compound shown in formula I
Often prop up the freeze-dried powder agent prescription composition of the compound (the tetra-acetylated glucopyranoside of 1-hydroxy-3-methoxy-6,7-diacetoxy xanthone-2-C-β-D-) prepared containing 15mg embodiment 1:
Preparation method: more than 100 grades in workshop, adds ethanol stirring and dissolving by compound prepared by embodiment 1, adds sodium-chlor, N.F,USP MANNITOL and appropriate water for injection, stir, add 0.1% pin activated carbon, absorption, filter decarburization, benefit injects water to specified amount, and millipore filtration membrane filtration, props up packing by 4mL/, lyophilize, encapsulation, through being up to the standards, to obtain final product.
The explanation of above embodiment just understands method of the present invention and core concept thereof for helping.It should be pointed out that for those skilled in the art, under the premise without departing from the principles of the invention, can also carry out some improvement and modification to the present invention, these improve and modify and also fall in the protection domain of the claims in the present invention.
Claims (12)
1. a compound shown in formula I,
Wherein, Ac is ethanoyl.
2. a preparation method for compound shown in formula I as claimed in claim 1, is characterized in that, under catalyst action, 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide react obtained in a solvent.
3. preparation method according to claim 2, it is characterized in that, the mol ratio of described 1,6,7-trihydroxy--3-methoxyl group xanthone-2-C-β-D-glucopyranoside and diacetyl oxide is 1.0:5.0 ~ 1.0:10.0.
4. preparation method according to claim 2, it is characterized in that, described catalyzer is acetate.
5. preparation method according to claim 4, it is characterized in that, described acetate is sodium acetate or potassium acetate.
6. preparation method according to claim 2, it is characterized in that, described solvent is Glacial acetic acid.
7. preparation method according to claim 2, it is characterized in that, temperature of reaction is 40 DEG C ~ 70 DEG C.
8. preparation method according to claim 2, it is characterized in that, the reaction times is 2h ~ 5h.
9. compound shown in formula I described in claim 1 is being prepared antitumor drug, prevention or treatment diabetes medicament or is having the application regulated in blood uric acid function medicament.
10. a pharmaceutical composition, is characterized in that, compound shown in formula I described in the claim 1 comprising treatment significant quantity.
11. 1 kinds of pharmaceutical preparations, is characterized in that, compound and pharmaceutically acceptable auxiliary material shown in formula I described in the claim 1 comprising treatment significant quantity.
12. according to pharmaceutical preparation described in claim 11, it is characterized in that, it is tablet, capsule, injection liquid or lyophilized injectable powder.
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| 芒果苷及其衍生物对糖尿病小鼠的降糖作用;蓝萍等;《中国动物保健》;20100630;51-53 * |
| 芒果苷酰化衍生物降血糖活性的研究;李学坚等;《时珍国医国药》;20130123;第24卷(第1期);21-22 * |
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