CN108570085B - Maleimide derivatives of the triazole structure containing xylose and the preparation method and application thereof - Google Patents
Maleimide derivatives of the triazole structure containing xylose and the preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses maleimide derivatives of a kind of triazole structure containing xylose and the preparation method and application thereof, N- p-hydroxyphenyl maleimide and acetyl xylose triazole salicylaldoxime are synthesized first, then N- p-hydroxyphenyl maleimide and acetyl xylose triazole salicylaldoxime are dissolved in dehydrated alcohol, carry out 1, 3- Dipolar Cycloaddition, import acetyl xylose triazole and isoxazole structure, finally intermediate compound is suspended in methanol, the methanol solution of sodium methoxide is slowly added dropwise under nitrogen protection, being heated to room temperature, the reaction was continued, ion exchange resin is washed with methanol, filtrate decompression obtains faint yellow solid after removing methanol, column chromatography for separation must contain the maleimide derivatives of xylose triazole structure.The maleimide derivatives of the triazole structure prepared by the present invention containing xylose have stronger inhibiting tumour cells effect, provide the foundation for its further field of medicaments application.
Description
Technical field
The invention belongs to pharmaceutical technology fields, more particularly to the triazole structure containing xylose maleimide derivatives and its
Preparation method and application.
Background technique
N- p-hydroxyphenyl maleimide, chemical name: 1- p-hydroxyphenyl -1H- pyrroles -2,5- diketone, chemical structural formula is such as
Under:
1,3- Dipolar Cycloaddition becomes synthesis five member ring heterocyclic compound with its good region and main selectivity
More active a kind of reaction in most important method and heterocyclic drug chemical research.In 1,2,3- triazole molecular structure
With armaticity and electronics abundant, there can be a variety of biologies by forming enzyme and acceptor interaction in hydrogen bond and organism
Activity.Glucoside compound is widely present in vivo, and plays the physiological function wanted emphatically, and sugar is introduced in compound molecule
Glycosides can increase its water-soluble and guiding performance, improve pharmacological property.
Recent studies suggest that some compounds containing glycosylation triazole are for carbonic anhydrase, glycosyl transferase and egg
White tyrosine phosphatase shows good inhibiting effect.So either still from a synthetic point of view from pharmacology, this
Heterocyclic compounds have very high synthesis to be worth.
Summary of the invention
The object of the present invention is to provide maleimide derivatives of a kind of triazole structure containing xylose and preparation method thereof
With application, the maleimide derivatives of the triazole structure containing xylose are prepared.
To achieve the goals above, technical solution of the present invention is as follows:
A kind of maleimide derivatives of the triazole structure containing xylose, which is characterized in that the knot of triazole containing xylose
The chemical structural formula of the maleimide derivatives of structure is as follows:
Wherein:
- Glu ' is the xylosyl being expressed from the next
A kind of preparation method of the maleimide derivatives of the triazole structure containing xylose, the preparation method include:
Maleic anhydride and para hydroxybenzene amine are dissolved in a certain amount of acetone solvent by step 1, under stiring will be right
Hydroxyanilines solution is added dropwise to the reaction flask containing maleic acid anhydride solution, and exothermic heat of reaction simultaneously gradually generates pale yellow precipitate,
Room temperature sequentially adds manganese acetate, triethylamine and aceticanhydride after the reaction was continued 2~3 hours in above-mentioned reaction flask, after heating precipitating by
Step dissolution, reacts 2~3 hours at 50~60 DEG C, and solution becomes red-black by orange, pours into ice water, analyses after being cooled to room temperature
It precipitates out, through massive laundering, drying, obtains product N- p-hydroxyphenyl maleimide with acetone recrystallization；
Step 2 generates acetyl xylose triazole water using acetyl xylose triazole salicylide and hydroxylamine hydrochloride dehydration
Poplar aldoxime；
N- p-hydroxyphenyl maleimide and acetyl xylose triazole salicylaldoxime are dissolved in dehydrated alcohol by step 3, are added
Enter toluene-sodium-sulfonchloramide, flow back 8~12 hours, carry out 1,3- Dipolar Cycloaddition, imports acetyl xylose triazole and isoxazole structure,
It is recrystallized with methanol, obtains intermediate compound；
Intermediate compound is suspended in methanol by step 4, and ice water is cooled to 0 DEG C, and sodium methoxide is slowly added dropwise under nitrogen protection
Methanol solution, being heated to room temperature, the reaction was continued 3~4 hours, TLC monitor to raw material point disappear, with 732 superacicd styrene sun from
Sub-exchange resin regulation system to neutrality, filtering is washed ion exchange resin with methanol, is obtained after filtrate decompression removing methanol yellowish
Color solid, column chromatography for separation must contain the maleimide derivatives of xylose triazole structure.
Further, the ratio between amount of the maleic anhydride and para hydroxybenzene amine substance is 1:1.
Further, the ratio between amount of the acetyl xylose triazole salicylide and hydroxylamine hydrochloride substance is 1:1.25.
Further, the N- p-hydroxyphenyl maleimide, acetyl xylose triazole salicylaldoxime, toluene-sodium-sulfonchloramide substance
The ratio between amount is 1:1:1.2.
Further, the ratio between amount of the intermediate compound and sodium methoxide substance is 1:2.
Further, the volume ratio of chloroform and methanol is 20:1 in the eluant, eluent that the column chromatography for separation uses.
The invention also provides a kind of maleimide derivatives of triazole structure containing xylose in terms of anti-tumor drug
Application.
A kind of maleimide derivatives and preparation method thereof of triazole structure containing xylose proposed by the present invention, the preparation
Method introduces isozole ring in N- substituted-phenyl maleimide structure with 1,3- dipole-diople interaction method, with xylose triazole
Derivatives reaction import xylose triazole structure, thus synthesis one novel triazole structure containing xylose maleimide
Derivative.The maleimide derivatives of the triazole structure prepared by the present invention containing xylose have stronger inhibiting tumour cells
Effect provides the foundation for its further field of medicaments application.
Detailed description of the invention
Fig. 1 is the preparation method flow chart of the maleimide derivatives of the triazole structure of the invention containing xylose；
Fig. 2 is that N- p-hydroxyphenyl maleimide of the present invention prepares chemical structural formula schematic diagram；
Fig. 3 is that the maleimide derivatives of the triazole structure of the invention containing xylose prepare chemical structural formula schematic diagram.
Specific embodiment
Technical solution of the present invention is described in further details with reference to the accompanying drawings and examples, following embodiment is not constituted
Limitation of the invention.
Isoxazole derivative is as a kind of useful intermediate and themselves shown a variety of pharmaceutical activity come out
And it gets more and more people's extensive concerning.Overall thought of the invention is by biologically active glucosides and 1,2,3- triazole drug effect
Structural unit is dexterously introduced into the structure of N- p-hydroxyphenyl five yuan of isozole rings of maleimide, has produced isoxazole wood
The maleimide derivatives of sugared triazole structure, N- p-hydroxyphenyl maleimide introduce biologically active glucosides and
1,2,3- triazole pharmacophore unit can change pharmacological activity.
The present invention provides a kind of maleimide derivatives of triazole structure containing xylose, chemical structural formula is as follows:
Wherein:
- Glu ' is the xylosyl being expressed from the next
The present embodiment is a kind of preparation method of the maleimide derivatives of triazole structure containing xylose, including following step
It is rapid:
Step S1, maleic anhydride and para hydroxybenzene amine are dissolved in a certain amount of acetone solvent, under stiring will
Para hydroxybenzene amine aqueous solution is added dropwise to the reaction flask containing maleic acid anhydride solution, and exothermic heat of reaction simultaneously gradually generates faint yellow sink
It forms sediment, room temperature sequentially adds manganese acetate, triethylamine and aceticanhydride after the reaction was continued 2~3 hours in above-mentioned reaction flask, sinks after heating
Shallow lake is gradually dissolved, and is reacted 2~3 hours at 50~60 DEG C, and solution becomes red-black by orange, pours into ice water after being cooled to room temperature
In, precipitating is precipitated, through massive laundering, drying, obtains product N- p-hydroxyphenyl maleimide with acetone recrystallization.
As shown in Fig. 2, chemical structural formula 1 is maleic anhydride in Fig. 2, chemical structural formula 2 is para hydroxybenzene amine, is passed through
N- p-hydroxyphenyl maleimide is generated after reaction, N- p-hydroxyphenyl maleimide corresponds to chemical structural formula 3.
Maleic anhydride and para hydroxybenzene amine are dissolved in a certain amount of acetone solvent by the present embodiment, are each formed
Then solution is reacted according to the ratio of the amount of substance (mole) 1:1, react 2~3 hours at room temperature, room temperature control
At 20~30 DEG C.Manganese acetate, triethylamine and aceticanhydride are sequentially added in above-mentioned reaction flask, are precipitated after heating and are gradually dissolved, 50
It is reacted 2~3 hours at~60 DEG C, solution becomes red-black by orange, pours into ice water after being cooled to room temperature, precipitating is precipitated, through big
Amount washing, drying, obtain product N- p-hydroxyphenyl maleimide with acetone recrystallization.
Step S2, acetyl xylose triazole bigcatkin willow is generated with acetyl xylose triazole salicylide and hydroxylamine hydrochloride dehydration
Aldoxime.
The present embodiment acetyl xylose triazole salicylide and hydroxylamine hydrochloride dehydration generate acetyl xylose triazole water
Poplar aldoxime, comprising:
Acetyl nitrine xylose, 2- propynyloxy benzaldehyde are suspended in the in the mixed solvent of methylene chloride and water, are warming up to
It 40~44 DEG C, is vigorously stirred down and sequentially adds sodium ascorbate and CuSO4·5H2O continues back flow reaction 4~5 hours, stops anti-
It answers, when the solution system wait chemically react is down to room temperature, liquid separation, water layer CH2C12It is extracted twice, merges organic phase, anhydrous sulphur
Sour sodium is dried overnight, and is filtered, and rapid column chromatography separates after solvent is removed under reduced pressure, and obtains acetyl xylose triazole salicylide；
Hydroxylamine hydrochloride and water are added in reaction flask, acetyl wood is added under stiring in magnetic agitation to hydroxylamine hydrochloride dissolved clarification
Sugared triazole salicylide and dehydrated alcohol are vigorously stirred 2~3 hours, after having reacted, use 20%Na2CO3Solution adjusts reaction
To neutrality, placement is cooled to room temperature, generates a large amount of white precipitates, after being put into refrigerator overnight, be filtered under diminished pressure the pH value of liquid, and room temperature is dry
It is dry, obtain granular white crystal acetyl xylose triazole salicylaldoxime.
Such as:
12mmol acetyl nitrine xylose, 1.60g (10mmo1) 2- propynyloxy benzaldehyde are suspended in 100mL (dichloromethane
Alkane): the in the mixed solvent of (water)=1:1 is warming up to 40~44 DEG C, is vigorously stirred down and sequentially adds 0.2mmol sodium ascorbate
With the CuSO of 0.1mmol4·5H2O continues back flow reaction 4~5 hours, stops reaction, and solution system to be chemically reacted is down to
When room temperature (20~30 DEG C), liquid separation, water layer CH2C12It is extracted twice (50mL × 2), merges organic phase, anhydrous sodium sulfate is dry
Overnight, it filters, rapid column chromatography separates after solvent is removed under reduced pressure, and obtains acetyl xylose triazole salicylide.
In the conical flask of 250mL, 35.6g (0.5mol) hydroxylamine hydrochloride and 90mL H is added2O, magnetic agitation to hydrochloric acid
Azanol dissolution (generallys use the stirring of magnetic agitation instrument).Under stiring, weigh (0.4mol) acetyl xylose triazole salicylide and
50mL dehydrated alcohol pours into 250mL conical flask, is vigorously stirred 2~3 hours.After having reacted, 20%Na is used2CO3Solution is about
300mL adjusts the pH value of reaction solution to neutrality, and placement is cooled to room temperature, and generates a large amount of white precipitates, after being put into refrigerator overnight,
It is filtered under diminished pressure, drying at room temperature, obtains granular white crystal acetyl xylose triazole salicylaldoxime.
Step S3, N- p-hydroxyphenyl maleimide and acetyl xylose triazole salicylaldoxime are dissolved in dehydrated alcohol,
Toluene-sodium-sulfonchloramide is added, flows back 12 hours, carries out 1,3- Dipolar Cycloaddition, imports xylose triazole and isoxazole structure, uses methanol
Recrystallization, vacuum drying obtain intermediate compound.
The present embodiment is by N- p-hydroxyphenyl maleimide (0.1mol) and acetyl xylose triazole salicylaldoxime
(0.1mol) is dissolved in dehydrated alcohol, is added toluene-sodium-sulfonchloramide (0.12mol), is flowed back 12 hours, and 1,3- Dipolar Cycloaddition is carried out,
Xylose triazole and isoxazole structure are imported, is recrystallized with methanol, vacuum drying obtains intermediate compound.
As shown in figure 3, chemical structural formula 3 is N- p-hydroxyphenyl maleimide in figure, chemical structural formula 4 is acetyl xylose
Triazole salicylaldoxime, chemical structural formula 5 are the intermediate compound generated.
Step S4, intermediate compound is suspended in methanol, ice water is cooled to 0 DEG C, and methanol is slowly added dropwise under nitrogen protection
The methanol solution of sodium, the reaction was continued 3~4 hours for room temperature, and TLC, which is monitored to raw material point, to disappear, and is handed over 732 superacicd styrene cations
Resin moderated system is changed to neutrality, filtering washs ion exchange resin with methanol, and filtrate decompression obtains pale yellow colored solid after removing methanol
Body, column chromatography for separation must contain the maleimide derivatives of xylose triazole structure.
5mmol intermediate compound is suspended in 20mL methanol by the present embodiment, and ice-water bath is cooled to 0 DEG C, under nitrogen protection
The methanol solution 0.6mL for the sodium methoxide that concentration is 1.0mol/L is slowly added dropwise.The reaction was continued 4 hours for room temperature, and TLC is monitored to raw material
Point disappears, and with 732 superacicd styrene cation exchange resin regulation systems to neutrality, filtering washs amberlite with methanol
Rouge for several times, filtrate decompression remove methanol after faint yellow solid, column chromatography for separation [eluant, eluent: volume ratio (chloroform: methanol=20:
1) maleimide derivatives of the triazole structure containing xylose], are obtained.
As shown in figure 3, chemical structural formula 6 is the maleimide derivatives of the triazole structure containing xylose generated.
Experimental data is as follows: the maleimide derivatives (compound 6) of the triazole structure containing xylose, pale yellow powder,
Yield 21.5%, fusing point: 106-107 DEG C, nucleus magnetic hydrogen spectrum data and Elemental analysis data are as follows:
1H NMR(DMSO-d6) δ: 7.31-7.48 (m, 4H, Ar-H), 8.30 (1H, s), 6.47 (s, 1H, C=C-H),
5.82 (d, J=7.2Hz, 1H), 5.34 (d, J=7.2Hz, 1H), 7.63 (1H, d, J=6.4Hz), 7.51 (1H, m), 7.33
(1H, d, J=4.0Hz), 7.03 (1H, t), 5.53 (1H, d, J=9.6Hz), 5.45 (1H, s), 5.35 (1H, s), 5.25 (2H,
s),5.20(1H,s),4.66
(1H, s), 4.36 (1H, t), 4.02 (1H, dd, J=3.2Hz, J=10.0Hz), 3.83 (1H, t), 3.68 (1H,
m)
IR(KBr)v/cm-1 3447,3413,2926,1712,1602,1458,1243,1097,1058,758
M/e:537 (100.0%)
Anal.calcd.for C25H23N5O9: C, 55.87；H,4.33；N,13.01
In-vitro Inhibitory Effect of the present embodiment using 6 pairs of compound different tumor strains of mtt assay measurement, triazole structure containing xylose
Maleimide derivatives antitumor cytolytic activity result it is as follows:
Compound 6 is dissolved with DMSO, dilute, tumour cell Bel-7402 (human liver cancer cell), KB (cancer cell of oral cavity),
SGC7901 (stomach cancer cell), HO8901 (ovarian cancer cell), HL-60 (leukaemia cell), ECA109 (colon-cancer cell) are in 96 holes
It is planted on plate into 4000/200 holes μ L/, 2 μ L of compound is added in every hole, final concentration of 12.0 μM, 6.0 μM, 3.0 μM, 1.5 μM, is total to
It is same as 37 DEG C, 5%CO2It is incubated for 72 hours in cell incubator, with DMSO (1%) for blank control.After 72 hours, it is added dense eventually
Degree is the MTT of 0.25mg/mL, is placed in 37 DEG C, 5%CO24 hours in cell incubator, solvent is blotted later, and 100 μ are added in every hole
L DMSO is measured at 570nm absorbance (OD value) with enzyme linked immunological instrument, and the data obtained is for calculating IC50Value.Inhibition is selected to live
Property high compound, measure influence of the compound effects time difference under various concentration to human tumor cells period and apoptosis.
The test-compound of various concentration carries out scalping with 96 orifice plates, according to resulting inhibiting rate, calculates IC50Value, as a result
It see the table below.
Table 1
In table 1, the maleimide derivatives (compound 6) for showing the triazole structure containing xylose are thin to six kinds of tumours
The IC of born of the same parents' strain50Value, illustrate compound to SGC7901 (stomach cancer cell), HL-60 (leukaemia cell), (human liver cancer is thin by Bel-7402
Born of the same parents) there is stronger inhibiting tumour cells effect, it provides the foundation for its further field of medicaments application.
The above embodiments are merely illustrative of the technical solutions of the present invention rather than is limited, without departing substantially from essence of the invention
In the case where mind and its essence, those skilled in the art make various corresponding changes and change in accordance with the present invention
Shape, but these corresponding changes and modifications all should fall within the scope of protection of the appended claims of the present invention.
Claims (8)
1. a kind of maleimide derivatives of triazole structure containing xylose, which is characterized in that the triazole structure containing xylose
Maleimide derivatives chemical structural formula it is as follows:
Wherein:
- Glu ' is the xylosyl being expressed from the next
2. a kind of preparation method of the maleimide derivatives of the triazole structure containing xylose as described in claim 1, special
Sign is that the preparation method includes:
Maleic anhydride and para hydroxybenzene amine are dissolved in a certain amount of acetone solvent by step 1, under stiring will be to hydroxyl
Aniline solution is added dropwise to the reaction flask containing maleic acid anhydride solution, and exothermic heat of reaction simultaneously gradually generates pale yellow precipitate, room temperature
After the reaction was continued 2~3 hours, manganese acetate, triethylamine and aceticanhydride are sequentially added in above-mentioned reaction flask, are precipitated after heating gradually molten
Solution, reacts 2~3 hours at 50~60 DEG C, and solution becomes red-black by orange, pours into ice water after being cooled to room temperature, and it is heavy to be precipitated
It forms sediment, through massive laundering, drying, obtains product N- p-hydroxyphenyl maleimide with acetone recrystallization；
Step 2 generates acetyl xylose triazole salicylide using acetyl xylose triazole salicylide and hydroxylamine hydrochloride dehydration
Oxime；
N- p-hydroxyphenyl maleimide and acetyl xylose triazole salicylaldoxime are dissolved in dehydrated alcohol by step 3, and chlorine is added
Amine T flows back 8~12 hours, carries out 1,3- Dipolar Cycloaddition, imports acetyl xylose triazole and isoxazole structure, uses first
Alcohol recrystallization, obtains intermediate compound, and the chemical structural formula of the intermediate compound is as follows:
Wherein,
Intermediate compound is suspended in methanol by step 4, and ice water is cooled to 0 DEG C, and the first of sodium methoxide is slowly added dropwise under nitrogen protection
Alcoholic solution, being heated to room temperature, the reaction was continued 3~4 hours, and TLC, which is monitored to raw material point, to disappear, and is handed over 732 superacicd styrene cations
Resin moderated system is changed to neutrality, filtering washs ion exchange resin with methanol, and filtrate decompression obtains pale yellow colored solid after removing methanol
Body, column chromatography for separation must contain the maleimide derivatives of xylose triazole structure.
3. the preparation method of the maleimide derivatives of the triazole structure containing xylose, feature exist as claimed in claim 2
In the ratio between amount of the maleic anhydride and para hydroxybenzene amine substance is 1:1.
4. the preparation method of the maleimide derivatives of the triazole structure containing xylose, feature exist as claimed in claim 2
In the ratio between amount of the acetyl xylose triazole salicylide and hydroxylamine hydrochloride substance is 1:1.25.
5. the preparation method of the maleimide derivatives of the triazole structure containing xylose, feature exist as claimed in claim 2
In the ratio between the N- p-hydroxyphenyl maleimide, amount of acetyl xylose triazole salicylaldoxime, toluene-sodium-sulfonchloramide substance are 1:1:
1.2。
6. the preparation method of the maleimide derivatives of the triazole structure containing xylose, feature exist as claimed in claim 2
In the ratio between amount of the intermediate compound and sodium methoxide substance is 1:2.
7. the preparation method of the maleimide derivatives of the triazole structure containing xylose as claimed in claim 2, the column layer
The volume ratio of chloroform and methanol is 20:1 in the eluant, eluent that analysis separation uses.
8. a kind of maleimide derivatives of the triazole structure containing xylose as described in claim 1 are preparing antineoplastic object space
The application in face.
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| CN101289481A (en) * | 2008-06-06 | 2008-10-22 | 四川大学 | Synthesis of N-aryl-3-(4-beta-D-allopyranoside phenyl)-5-formyl isoxazole-4-methane amide |
| CN102276673A (en) * | 2011-06-21 | 2011-12-14 | 中国科学院成都生物研究所 | Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound |
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| CN102276673A (en) * | 2011-06-21 | 2011-12-14 | 中国科学院成都生物研究所 | Preparation method of 2-deoxy-beta-D-glucopyranosyl triazole compound |
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