CN105924445B - Pyrazoles N- p-nitrophenyl maleimide derivatives containing chromone structure and preparation method and application - Google Patents
Pyrazoles N- p-nitrophenyl maleimide derivatives containing chromone structure and preparation method and application Download PDFInfo
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Abstract
The invention discloses one kind 3（The oxygen 4H chromones of 6 bromine 4）1 phenyl 5 p-nitrophenyl 1,6a pyrrolin quinoline [3,4 c] pyrazoles 4,6（3aH,5H）Diketone and preparation method and application, the preparation method introduces on the basis of five yuan of pyrazole rings the structure for having imported chromone with 1,3 dipole-diople interaction method in N p-nitrophenyls maleimide, so as to synthesize one new 3（The oxygen 4H chromones of 6 bromine 4）1 phenyl 5 p-nitrophenyl 1,6a pyrrolin quinoline [3,4 c] pyrazoles 4,6（3aH,5H）Diketone, above-claimed cpd has good inhibitory action for tumor cell line, wherein there is more preferable inhibiting rate and selectivity for colon-cancer cell, human liver cancer cell, leukaemia etc., preparing antineoplastic etc., there is extraordinary prospects for commercial application.
Description
Technical field
The present invention relates to a kind of new pyrazoles N- p-nitrophenyl maleimide derivatives containing chromone structure, tool
Body refers to 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -4,
6 (3aH, 5H)-diketone and preparation method and application.
Background technology
N- p-nitrophenyl maleimides, chemical name：1- p-nitrophenyl pyrrolidines -2,5- diketone, chemical structural formula
It is as follows：
1- p-nitrophenyl pyrrolidine-2,5-diones
1,3- Dipolar Cycloadditions are with its good region and main selectivity and as synthesis five member ring heterocyclic compound
More active a kind of reaction in most important method, and heterocyclic drug chemical research.In recent years, because chromone is extensive
Bioactivity, anticancer, antibacterial, suppress platelet aggregation etc. and receive much attention.So either from pharmacology still from conjunction
Angled to consider, this heterocyclic compounds has very high synthesis value.
Pyrazole derivatives as a kind of useful intermediate and themselves shown multi-medicament activity out and
Get more and more people's extensive concerning.The present invention is assembled and to caused by pharmacological activity by studying different heterocycles in same molecule
Influence, so as to provide a kind of brand-new pyrazoles N- p-nitrophenyl maleimide derivatives containing chromone structure.
The content of the invention
The first aspect of the present invention purpose is to provide a kind of new pyrazoles N- p-nitrophenyl horses containing chromone structure
Carry out imide derivative.
The technical scheme that the present invention takes is as follows：
A kind of pyrazoles N- p-nitrophenyl maleimide derivatives containing chromone structure, its chemical name are：3-
(the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -4,6 (3aH,
5H)-diketone, its structural formula are as follows：
The compound relevant experimental data is as follows：
。
Applicant is had found by studying：Substituted using chromone derivative in the structure of pyrazoles, to N- p-nitrophenyls
Base maleimide carries out structure of modification, obtains a kind of brand-new pyrazoles N- p-nitrophenyls Malaysia containing chromone structure
Imide derivative, the compound can change pharmacological activity.
The second aspect of the present invention purpose is to provide a kind of above-mentioned pyrazoles N- p-nitrophenyl horses containing chromone structure
Carry out the preparation method of imide derivative, it is characterised in that comprise the following steps：Maleic anhydride and paranitroanilinum is anti-
N- p-nitrophenyls maleimide (3) should be synthesized, then has the 6- bromos chromone that carboxaldehyde radicals substitutes to be dehydrated with phenylhydrazine using 3
Reaction synthesis 6- bromo chromone phenylhydrazones (4), finally by N- p-nitrophenyls maleimide (3) and 6- bromo chromone phenylhydrazones (4)
Dipolar Cycloaddition is carried out, synthesizes 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyl -1,6a- dihydro pyrroles
Cough up quinoline [3,4-c] pyrazoles -4,6 (3aH, 5H)-diketone (5).
Reaction equation of the present invention is as follows：
Further, a kind of described 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- bis-
The preparation method of hydrogen pyrrolin [3,4-c] pyrazoles -4,6 (3aH, 5H)-diketone, it is characterised in that comprise the following steps：
(1), the synthesis of N- p-nitrophenyls maleimide：
Maleic anhydride and paranitroanilinum are dissolved in acetone solvent, reacts and progressively produces yellowish under agitation
Color precipitates, and after reacting at room temperature 1 hour, takes a small amount of precipitation, through washing, dries, sequentially adds manganese acetate, triethylamine and aceticanhydride, rises
Wen Hou, precipitation progressively dissolve, reacted 2 hours at 50~60 DEG C, and solution becomes red-black by orange, engenders new precipitation,
Room temperature is cooled to, precipitates through washing, dry in water, product N- p-nitrophenyls maleimide (3) is obtained with acetone recrystallization
(2), the synthesis of 6- bromos chromone phenylhydrazone:
Described 6- bromo chromone phenylhydrazones (4) are known compound, and No. CAS is 68287-82-1, and the present invention uses 3
The method for having the 6- bromos chromone that carboxaldehyde radicals substitutes and phenylhydrazine dehydration generation schiff bases is synthesized：Take 2mmol phenylhydrazine
Add in the flask for filling 10mL tetrahydrofurans, then boiling water bath return stirring is slowly added dropwise into 20mL dissolved with 2mmol to dissolving
The ethanol solution of 3 6- bromo chromones for having carboxaldehyde radicals to substitute, continues boiling water bath return stirring 1h, and 10 drop hydrochloric acid are added dropwise,
There is pale yellow precipitate appearance；Continuous boiling water bath return stirring 5h, stops water-bath, adds people 20mL distilled water to stir, pale yellow precipitate
Darken, filter to obtain 6- bromo chromone phenylhydrazones, be yellowish red color needle-like product, rinsed repeatedly, be dried in vacuo with absolute ether
Product 6- bromo chromone phenylhydrazones (4)；
(3), 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyl -1,6a- pyrrolin quinolines [3,4-c]
The synthesis of pyrazoles -4,6 (3aH, 5H)-diketone：
By 1mmol N- p-nitrophenyls maleimides (3) and 1.1mmol 6- bromo chromone phenylhydrazones (4) in 20mL second
In alcohol, 1.2mL toluene-sodium-sulfonchloramides are added, are flowed back 12 hours, precipitation is filtered, cleaning, is recrystallized with methanol, is obtained after vacuum drying
Product 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -4,
6 (3aH, 5H)-diketone (5).
Further it is provided in：
In described step (1), the pale yellow precipitate for reacting to obtain need to be filtered under diminished pressure.
The third aspect of the present invention purpose is to provide a kind of 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- to nitro
Phenyl -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -4,6 (3aH, the 5H)-application of diketone in terms of antineoplastic is prepared.
Pass through experimental verification：Above-claimed cpd is thin for different knurl strains such as human liver cancer cell, cancer cell of oral cavity, stomach cancer cell, oophoroma
Born of the same parents, leukaemia, colon-cancer cell etc., are respectively provided with inhibitory action, wherein for ECA109 (colon-cancer cell), Bel-7402 (people
Liver cancer cells), HL-60 (leukaemia) etc. there is more preferably inhibiting rate and selectivity, can be manufactured separately antineoplastic,
Active component can be used as to prepare anti-tumor compositions with other antineoplastics, there is extraordinary prospects for commercial application.
Beneficial effects of the present invention are as follows：
The applicant it has been investigated that, substituted using chromone derivative in the structure of pyrazoles, to N- p-nitrophenyls
Base maleimide carries out structure of modification, obtains a kind of brand-new pyrazoles N- p-nitrophenyls Malaysia containing chromone structure
Imide derivative, the compound can change pharmacological activity, through further experiment and analysis, study different heterocycles at same point
Assemble in son and influence caused by pharmacological activity, applicant have been synthesized containing chromone structure by Dipolar Cycloaddition
Pyrazoles N- p-nitrophenyl maleimide derivatives, the new pyrazoles N- containing chromone structure prepared by this method is to nitre
Base phenyl maleimide derivative, in terms of antineoplastic is prepared, there is extraordinary prospects for commercial application.
Embodiment
Toluene-sodium-sulfonchloramide：English name Chloramine-T, chemical constitution are
The present invention is described further with reference to embodiments, but embodiment should not be construed as limiting the model of the present invention
Enclose.
The synthesis of embodiment 1, N- p-nitrophenyl maleimides：
Maleic anhydride and paranitroanilinum are dissolved in a certain amount of acetone solvent, under agitation will be to nitro
Aniline solution is added dropwise to the reaction bulb containing maleic acid anhydride solution, and exothermic heat of reaction simultaneously progressively produces pale yellow precipitate, room temperature
Reaction 1 hour after, take a small amount of precipitation, through washing, dry, sequentially add manganese acetate, triethylamine and aceticanhydride, after heating, precipitate by
Step dissolving, reacts 2 hours at 50~60 DEG C, and solution becomes red-black by orange, engenders new precipitation, is cooled to room temperature,
Precipitation obtains product N- p-nitrophenyls maleimide (3) through massive laundering, drying with acetone recrystallization in water.
The synthesis of embodiment 2,6- bromo chromone phenylhydrazones：
2mmol phenylhydrazine is taken to add in the flask for filling 10mL tetrahydrofurans, boiling water bath return stirring to dissolving, Ran Houhuan
It is slow to be added dropwise to ethanol solutions of the 20mL dissolved with 3 6- bromo chromones for thering is carboxaldehyde radicals to substitute of 2mmol, continue boiling water bath and return
Stream stirring 1h, 10 drop hydrochloric acid are added dropwise, there is pale yellow precipitate appearance.Continuous boiling water bath return stirring 5h, stops water-bath, adds people 20mL
Distilled water stirs, and pale yellow precipitate darkens, and filters to obtain phenylhydrazone, yellowish red color needle-like product.Rinsed repeatedly, very with absolute ether
Empty dry product 6- bromo chromone phenylhydrazones (4).
Embodiment 3,3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyl -1,6a- pyrrolin quinoline [3,
4-c] pyrazoles -4,6 (3aH, 5H)-diketone synthesis：
By 1mmol N- p-nitrophenyls maleimides (3) and 1.1mmol 6- bromo chromone phenylhydrazones (4) in 20mL second
In alcohol, 1.2mL toluene-sodium-sulfonchloramides are added, are flowed back 12 hours.Precipitation is filtered, cleaning, is recrystallized with methanol, is obtained after vacuum drying
Product 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -4,
6 (3aH, 5H)-diketone (5).Product is yellow crystal, yield 17.2%, m.p.123.5-125 DEG C.
Compound (5) structural confirmation：C26H15BrN4O6
1H NMR(DMSO)δ:7.245-7.502 (m, 12H, Ar-H), 6.48 (s, 1H, C=C-H), 5.83 (d, J=
1010Hz, 1H), 5.34 (d, J=1014Hz, 1H),
IR 3457 (N-C=O), 3085 (ArH), 1720 (C=O), 1577 (C=N), 1296 (C-O-C) cm-1
m/e:560.02 (100.0%), 558.02 (97.3%), 559.02 (27.8%).
Anal.calcd.for C26H15BrN4O6：C,55.83；H,2.70；N,10.02.
Application Example 4：Antitumor activity using mtt assay detection test-compound (5) to different knurl strains.
Compound (5) prepared by above-described embodiment, with different knurl strains, [(human liver cancer is thin by tumour cell Bel-7402 respectively
Born of the same parents), KB (cancer cell of oral cavity), SGC7901 (stomach cancer cell), HO8901 (ovarian cancer cell), HL-60 (leukaemia),
ECA109 (colon-cancer cell)] it is experimental subjects, In-vitro Inhibitory Effect of the test compound (5) for different knurl strains：Experiment uses
The micro enzyme reaction colorimetric method (mtt assay) of tetramethyl azo azoles salt, activity represent (IC with half-inhibition concentration50)。
Specific experiment step is as follows：
Compound (5) is dissolved with DMSO, diluted, tumour cell Bel-7402 (human liver cancer cell), (carcinoma of mouth is thin by KB
Born of the same parents), SGC7901 (stomach cancer cell), HO8901 (ovarian cancer cell), HL-60 (leukaemia), ECA109 (colon-cancer cell)
Planted on 96 orifice plates into 4000/200 μ L/ holes, add compound 2 μ L per hole, final concentration of 12.0 μM, 6.0 μM, 3.0 μM,
1.5 μM, jointly in 37 DEG C, 5%CO2It is incubated 72 hours in cell culture incubator, with DMSO (1%) for blank control.After 72 hours,
Final concentration of 0.25mg/mL MTT is added, is placed in 37 DEG C, 5%CO24 hours in cell culture incubator, solvent is blotted afterwards, per hole
100 μ l DMSO are added, determine absorbance (OD values) at 570nm with enzyme linked immunological instrument, the data obtained is used to calculate IC50Value.Choose
The compound that inhibitory activity is high is selected, determines the compound effects time difference under various concentrations to human tumor cells cycle and apoptosis
Influence.
The test-compound of various concentrations carries out scalping with 96 orifice plates, according to the inhibiting rate of gained, calculates IC50Value, as a result
It see the table below.
Table 1, pyrazoles N-p-nitrophenyl maleimide derivatives are to the IC of six kinds of tumor cell lines50Value
。
It can be seen that by upper table data：Compound prepared by the present invention, suppression is respectively provided with for six kinds of tumor cell lines
Effect, wherein having more for ECA109 (colon-cancer cell), Bel-7402 (human liver cancer cell), HL-60 (leukaemia) etc.
Good inhibiting rate and selectivity, can be manufactured separately antineoplastic, can also be used as active component and other antineoplastics
Anti-tumor compositions are prepared, there is extraordinary prospects for commercial application.
Claims (5)
1. a kind of pyrazoles N- p-nitrophenyl maleimide derivatives containing chromone structure, its chemical name are：3-(6-
Bromo- 4- oxygen -4H- chromones) -1- phenyl -5- p-nitrophenyls -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -4,6 (3aH, 5H) -
Diketone, its structural formula are as follows：
A kind of 2. 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- pyrrolin quinoline [3,4-c] pyrrole
The preparation method of azoles -4,6 (3aH, 5H)-diketone, it is characterised in that comprise the following steps：By maleic anhydride and to nitro
Aniline reaction synthesizes N- p-nitrophenyl maleimides, then using the 3 6- bromos chromones and phenylhydrazine for having carboxaldehyde radicals to substitute
Dehydration synthesizes 6- bromo chromone phenylhydrazones, finally carries out N- p-nitrophenyls maleimide and 6- bromo chromones phenylhydrazone even
Polar ring addition reaction, synthesis 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyl -1,6a- pyrrolin quinoline [3,
4-c] pyrazoles -4,6 (3aH, 5H)-diketone.
A kind of 3. 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- according to claim 2
The preparation method of pyrrolin quinoline [3,4-c] pyrazoles -4,6 (3aH, 5H)-diketone, it is characterised in that comprise the following steps：
(1) synthesis of N- p-nitrophenyls maleimide：
Maleic anhydride and paranitroanilinum are dissolved in acetone solvent, reacts under agitation and progressively produces faint yellow sink
Form sediment, after reacting at room temperature 1 hour, take a small amount of precipitation, through washing, dry, sequentially add manganese acetate, triethylamine and aceticanhydride, after heating,
Precipitation progressively dissolves, and is reacted 2 hours at 50~60 DEG C, and solution becomes red-black by orange, engenders new precipitation, is cooled to
Room temperature, in water precipitation through washing, dry, obtain product N- p-nitrophenyl maleimides with acetone recrystallization；
(2) synthesis of 6- bromos chromone phenylhydrazone:
2mmol phenylhydrazine is taken to add in the flask for filling 10mL tetrahydrofurans, then boiling water bath return stirring slowly drips to dissolving
Ethanol solutions of the 20mL dissolved with 3 6- bromo chromones for having carboxaldehyde radicals to substitute of 2mmol is added, continues boiling water bath backflow and stirs
1h is mixed, 10 drop hydrochloric acid are added dropwise, there is pale yellow precipitate appearance；Continuous boiling water bath return stirring 5h, stops water-bath, adds people 20mL to distill
Water stirs, and pale yellow precipitate darkens, filters to obtain 6- bromo chromone phenylhydrazones, be yellowish red color needle-like product, rushed with absolute ether
Wash repeatedly, be dried in vacuo to obtain product；
(3) 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -
The synthesis of 4,6 (3aH, 5H)-diketone:
By 1mmol N- p-nitrophenyls maleimides and 1.1mmol 6- bromo chromone phenylhydrazones in 20mL ethanol, add
1.2mL toluene-sodium-sulfonchloramides, flow back 12 hours, precipitation is filtered, cleaning, recrystallized with methanol, product 3- is obtained after vacuum drying, and (6- is bromo-
4- oxygen -4H- chromones) -1- phenyl -5- p-nitrophenyl -1,6a- pyrrolin quinoline [3,4-c] pyrazoles -4,6 (3aH, 5H)-two
Ketone.
A kind of 4. 3- (the bromo- 4- oxygen -4H- chromones of 6-) -1- phenyl -5- p-nitrophenyls -1,6a- according to claim 3
The preparation method of pyrrolin quinoline [3,4-c] pyrazoles -4,6 (3aH, 5H)-diketone, it is characterised in that：In described step (1),
Reacting obtained pale yellow precipitate need to be filtered under diminished pressure.
A kind of 5. application of the compound in terms of antineoplastic is prepared described in claim 1.
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