CN107235887A - A kind of polysubstituted diindolylmethane derivative and preparation method thereof - Google Patents
A kind of polysubstituted diindolylmethane derivative and preparation method thereof Download PDFInfo
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- CN107235887A CN107235887A CN201710440331.0A CN201710440331A CN107235887A CN 107235887 A CN107235887 A CN 107235887A CN 201710440331 A CN201710440331 A CN 201710440331A CN 107235887 A CN107235887 A CN 107235887A
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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Abstract
The present invention relates to a kind of polysubstituted diindolylmethane derivative and preparation method thereof, shown in its structural formula such as formula (I)：Wherein, R1For substituted aromatic base or alkyl, R2It is alkoxy, halogen or alkyl；The substituted aromatic base is phenyl, and naphthyl, alkyl includes：Methyl, ethyl, cyclohexyl.Preparation method is as follows：At room temperature, in a nitrogen atmosphere, by the nitrone derivative shown in formula (II), photochemical catalyst dissolving shown in indole structure compound and formula (IV) shown in formula (III) is in organic solvent, it is well mixed, it is placed in after illumination a few hours question response is complete under blue led s lamps other visible light sources such as (or) incandescent lamps, rotates solvent, again through silica gel column chromatography separating purification, you can obtain polysubstituted diindolylmethane derivative.The present invention solves the problem of existing diindolylmethane derivative synthesis needs transition metal-catalyzed system, low yield, method feature of environmental protection difference, and reaction condition is gentle, method is simple and easy to operate, yield is high.
Description
Technical field
The present invention relates to a kind of polysubstituted diindolylmethane derivative and preparation method thereof, belong to organic synthesis technology
Field.
Background technology
Di-indole methyl hydride widely exists in natural products and medicine with bioactivity as important molecular skeleton
Among thing molecule, antibacterial, anti-inflammatory, antimycotic and antibacterial activity characteristic are shown, such as following formula, compound 1-3 is typically to contain
There are the natural products or pharmaceutical intermediate of di-indole methyl hydride skeleton, compound 1 is a kind of from Escherichia coli extract solution
Molecule, compound 2 can then be obtained from pathogenic Halophiles extract solution, and compound 3 has the effect of anticancer, especially exists
In terms of anti-breast cancer.Therefore the synthesis of di-indole methyl hydride class compound has an important significance.
At present, polysubstituted diindolylmethane derivative report is synthesized and few, and existing synthetic method was used mostly
Metal catalyst system system is crossed, this just inevitably causes metal residual, while greatly pollution is produced to environment and is destroyed,
And complex steps.Therefore, seek to the diindolylmethane derivative that a kind of mild condition, method are simple and easy to operate yield is high
Synthetic method be current urgent problem to be solved.
The content of the invention
It is an object of the invention to solve the deficiencies in the prior art, there is provided a kind of new diindolylmethane derivative.
The second object of the present invention is to provide a kind of synthetic method of diindolylmethane derivative.
The technical solution adopted for the present invention to solve the technical problems is：
A kind of diindolylmethane derivative, shown in its structural formula such as formula (I)：
Wherein, R1For substituted aromatic base or alkyl, R2It is alkoxy, halogen or alkyl；The substituted aromatic base is benzene
Base, naphthyl, alkyl includes：Methyl, ethyl, cyclohexyl.
Preferably, the substituted aromatic base is phenyl.
The method for preparing diindolylmethane derivative of the present invention, comprises the following steps：
At room temperature, in a nitrogen atmosphere, by the nitrone derivative shown in formula (II), the indole structure shown in formula (III)
Photochemical catalyst dissolving shown in compound and formula (IV) is well mixed in organic solvent, is placed in blue led s lamps (or incandescent lamp
Deng other visible light sources) under illumination a few hours question response it is complete after, solvent is rotated, then through silica gel column chromatography separating purification, you can
Obtain polysubstituted diindolylmethane derivative.
Wherein, R2Can be alkoxy, halogen or alkyl.The reaction scheme is：
Preferably, the compound shown in the formula (III) is N- methyl indol compounds.
Preferably, the molar ratio of the nitrone derivative, indole structure compound and photochemical catalyst is 1: 3:
0.025。
Preferably, the organic solvent is selected from dichloromethane, dichloroethanes, acetonitrile or tetrahydrofuran.
Preferably, the volume that feeds intake of the organic solvent is 10-20mL/mmol nitrone.
The irradiation reaction time such as (or incandescent lamp other visible light sources) is 12- preferably, the blue led s lamps
20h。
Preferably, the silica gel column chromatography separating purification solvent for use is the mixed solvent of petroleum ether and ethyl acetate.
It is further preferred that the volume ratio of the petroleum ether and ethyl acetate is 20-10: 1.
Beneficial effects of the present invention are：
1st, the invention provides a kind of polysubstituted diindolylmethane derivative, there is the derivative huge potential source biomolecule to live
Property and researching value.According to existing document and patent report, polysubstituted diindolylmethane derivative has more bioactivity,
So the compound that the present invention is provided has higher researching value, the screening that may be used as lead compound is used and supplied
The R＆D institutions such as biological activity test research use.The present invention can also contain diindolylmethane derivative as other are synthesized
Raw material is used.
2nd, the invention provides a kind of method of the polysubstituted diindolylmethane derivative of succinct one-step synthesis method, this method
The problem of existing diindolylmethane derivative synthesis needs transition metal-catalyzed system, low yield, method feature of environmental protection difference is solved,
Seek to the diindolylmethane derivative synthetic route that a kind of mild condition, method are simple and easy to operate yield is high.
Embodiment
In order that technical scheme and advantage are more clearly understood, with reference to embodiments the present invention is entered to advance
One step is described in detail.It should be appreciated that specific embodiment described herein is not used to limit this hair only to explain the present invention
It is bright.
Embodiment 1
Into 10mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 118mg (0.9mmol) N- methyl Yin are added
Indole compound, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, lead to nitrogen and are placed in after 30 minutes after stirring
Under blue led s lamps, illumination reaction 20h at room temperature.After reaction terminates, after the rotated evaporimeter concentration of reaction dissolvent is spin-dried for,
Petroleum ether using volume ratio as 20: 1 again：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying point as eluant, eluent
From obtaining corresponding polysubstituted diindolylmethane derivative, its reaction equation is：
Product purity is 99%, and yield is 61%.Its1H NMR spectras see appendix 1,13C NMR spectrograms see appendix 2, nuclear-magnetism
Data analysis is：1H NMR (400MHz, CDCl3)：δH7.38-7.33 (m, 4H), 7.28 (d, J=8.2Hz, 4H), 7.21-
(s, the 6H) of 7.17 (m, 3H), 6.98 (t, J=7.4Hz, 2H), 6.52 (s, 2H), 5.87 (s, 1H), 3.66
13C NMR (100MHz, CDCl3)：δC144.5,137.4,128.7,128.3,128.2,127.5,126.1,
121.4,120.1,118.7,118.3,109.1,40.1,32.7.
Embodiment 2
Into 10mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 131mg (0.9mmol) N- methyl -4- are added
Methyl indol compound, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, lead to nitrogen 30 minutes after stirring
After be placed under blue led s lamps, illumination reaction 12h at room temperature.After reaction terminates, the rotated evaporimeter concentration rotation of reaction dissolvent
After dry, then the petroleum ether using volume ratio as 20: 1：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying as eluant, eluent
Separation, obtains corresponding polysubstituted diindolylmethane derivative, and its reaction equation is：
Product purity is 99%, and yield is 84%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH7.38
(d, J=7.2Hz, 2H), 7.32 (t, J=7.5Hz, 2H), 7.27-7.21 (m, 5H), 7.07 (d, J=8.8Hz, 2H), 6.50
(s, 2H), 5.87 (s, 1H), 3.69 (s, 6H), 2.41 (s, 6H)
13C NMR (100MHz, CDCl3)：δC144.7,135.9,128.7,128.5,128.2,127.8,127.7,
126.0,123.1,119.6,117.8,108.8,39.9,32.8,21.5.
Embodiment 3
Into 10mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 189mg (0.9mmol) N- methyl -4- are added
Bromo indole compound, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, led to nitrogen after 30 minutes after stirring
It is placed under blue led s lamps, at room temperature illumination reaction 12h.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent is spin-dried for
Afterwards, then the petroleum ether using volume ratio as 20: 1：The mixed solution of ethyl acetate carries out silica gel column chromatography purifying point as eluant, eluent
From obtaining corresponding polysubstituted diindolylmethane derivative, its reaction equation is：
Product purity is 99%, and yield is 48%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH 7.51
(s, 2H), 7.33-7.28 (m, 7H), 7.18 (d, J=8.7Hz, 2H), 6.53 (s, 2H), 5.78 (s, 1H), 3.69 (s, 6H)
13C NMR (100MHz, CDCl3)：δC143.5,136.1,129.4,128.9,128.52,128.45,126.5,
124.5,122.3,117.6,112.3,110.8,39.7,32.9.
Embodiment 4
Into 10mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 145mg (0.9mmol) N- methyl -4- are added
Methoxy-Indole compound, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, lead to 30 points of nitrogen after stirring
It is placed in after clock under blue led s lamps, at room temperature illumination reaction 16h.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent
After being spin-dried for, then the petroleum ether using volume ratio as 15: 1：The mixed solution of ethyl acetate carries out silica gel column chromatography pure as eluant, eluent
Change separation, obtain corresponding polysubstituted diindolylmethane derivative, its reaction equation is：
Product purity is 99%, and yield is 86%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH 7.47
(d, J=7.5Hz, 2H), 7.38 (t, J=7.5Hz, 2H), 7.32-7.25 (m, 3H), 6.98-6.92 (m, 4H), 6.63 (s,
2H), (s, the 6H) of 5.89 (s, 1H), 3.80 (s, 6H), 3.71
13C NMR (100MHz, CDCl3)：δC153.6,144.6,133.0,129.1,128.9,128.4,127.9,
126.2,117.7,111.6,110.0,102.2,56.0,40.3,32.9.
Embodiment 5
Into 10mL round-bottomed flasks, 59mg (0.3mmol) diphenyl nitrone, 186mg (0.9mmol) N- benzyls Yin are added
Indole compound, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, lead to nitrogen and are placed in after 30 minutes after stirring
Under blue led s lamps, illumination reaction 18h at room temperature.After reaction terminates, after the rotated evaporimeter concentration of reaction dissolvent is spin-dried for,
Again by the mixed solution of 20: 1 petroleum ether: ethyl acetate of volume ratio as eluant, eluent, silica gel column chromatography purifying point is carried out
From obtaining corresponding polysubstituted diindolylmethane derivative, its reaction equation is：
Product purity is 99%, and yield is 31%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH 7.41
(d, J=7.9Hz, 2H), 7.37 (d, J=7.5Hz, 2H), 7.29-7.20 (m, 11H), 7.11 (t, J=7.6Hz, 2H),
(s, the 4H) of 7.03 (d, J=7.2Hz, 4H), 6.98 (t, J=7.5Hz, 2H), 6.65 (s, 2H), 5.93 (s, 1H), 5.22
13C NMR (100MHz, CDCl3)：δC144.1,137.9,137.1,128.8,128.7,128.3,128.0,
127.8,127.4,126.5,126.1,121.7,120.2,119.0,118.8,109.7,50.0,40.3.
Embodiment 6
Into 10mL round-bottomed flasks, 61mg (0.3mmol) N- phenyl-α-cyclohexyl nitrone, 118 mg (0.9mmol) is added
N- methyl indol compounds, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, lead to 30 points of nitrogen after stirring
It is placed in after clock under blue led s lamps, at room temperature illumination reaction 12h.After reaction terminates, the rotated evaporimeter concentration of reaction dissolvent
After being spin-dried for, then the petroleum ether using volume ratio as 20: 1：The mixed solution of ethyl acetate carries out silica gel column chromatography pure as eluant, eluent
Change separation, obtain corresponding polysubstituted diindolylmethane derivative, its reaction equation is：
Product purity is 99%, and yield is 71%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH 7.67
(d, J=8.0Hz, 2H), 7.22 (d, J=8.2Hz, 2H), 7.17-7.14 (m, 2H), 7.06-7.03 (t, 2H), 6.92 (s,
2H), 4.23 (d, J=9.0Hz, 1H), 3.67 (s, 6H), 2.22-2.16 (m, 1H), 1.82 (d, J=12.6Hz, 2H),
1.67-1.61 (m, 3H), 1.25-1.19 (m, 2H), 1.06-0.99 (m, 2H)
13C NMR (100MHz, CDCl3)：δC137.0,128.3,126.4,121.2,119.8,118.46,118.45,
109.1,43.5,40.1,32.7,32.5,26.83,26.79.
Embodiment 7
Into 10mL round-bottomed flasks, 65mg (0.3mmol) N- phenyl-α -4- fluorophenyl nitrones, 118mg are added
(0.9mmol) N- methyl indol compounds, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, after stirring
Logical nitrogen is placed in after 30 minutes under blue led s lamps, at room temperature illumination reaction 12h.After reaction terminates, reaction dissolvent is rotated
After evaporimeter concentration is spin-dried for, then the petroleum ether using volume ratio as 20: 1：The mixed solution of ethyl acetate carries out silicon as eluant, eluent
Gel column chromatography eluting separation, obtains corresponding polysubstituted diindolylmethane derivative, and its reaction equation is：
Product purity is 99%, and yield is 67%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH 7.35
(d, J=7.9Hz, 2H), 7.29-7.27 (m, 4H), 7.21-7.18 (m, 2H), 7.01-6.93 (m, 4H), 6.50 (s, 2H),
(s, the 3H) of 5.85 (s, 1H), 3.66 (s, 6H), 5.83 (s, 1H), 3.64 (s, 6H), 2.31
13C NMR (100MHz, CDCl3)：δC161.4 (d, J=243.7Hz), 140.2,137.5,130.1 (d, J=
7.7Hz), 128.3,127.4,121.6,120.0,118.8,118.2,115.0 (d, J=21.0Hz), 109.2,39.4,
32.8.
Embodiment 8
Into 10mL round-bottomed flasks, 63mg (0.3mmol) N- phenyl-α -4- aminomethyl phenyl nitrones, 118mg are added
(0.9mmol) N- methyl indol compounds, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, after stirring
Logical nitrogen is placed in after 30 minutes under blue led s lamps, at room temperature illumination reaction 12h.After reaction terminates, reaction dissolvent is rotated
After evaporimeter concentration is spin-dried for, then the petroleum ether using volume ratio as 20: 1：The mixed solution of ethyl acetate carries out silicon as eluant, eluent
Gel column chromatography eluting separation, obtains corresponding polysubstituted diindolylmethane derivative, and its reaction equation is：
Product purity is 99%, and yield is 56%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH
7.38-7.37 (m, 2H), 7.27-7.26 (m, 2H), 7.22-7.21 (m, 2H), 7.19-7.16 (m, 2H), 7.07-7.06 (m,
2H), (s, the 3H) of 6.99-6.96 (m, 2H), 6.52 (s, 2H), 5.83 (s, 1H), 3.64 (s, 6H), 2.31
13C NMR (100MHz, CDCl3)：δC141.5,137.5,135.5,129.0,128.6,128.3,127.6,
1215,120.2,118.7,118.5,109.1,39.8,32.7,21.2.
Embodiment 9
Into 10mL round-bottomed flasks, 65mg (0.3mmol) N- phenyl-α -2- fluorophenyl nitrones, 118mg are added
(0.9mmol) N- methyl indol compounds, 1.2mg (0.0075mmol) photochemical catalysts and 5mL dichloromethane, after stirring
Logical nitrogen is placed in after 30 minutes under blue led s lamps, at room temperature illumination reaction 18h.After reaction terminates, reaction dissolvent is rotated
After evaporimeter concentration is spin-dried for, then the petroleum ether using volume ratio as 15: 1：The mixed solution of ethyl acetate carries out silicon as eluant, eluent
Gel column chromatography eluting separation, obtains corresponding polysubstituted diindolylmethane derivative, and its reaction equation is：
Product purity is 99%, and yield is 81%.Nuclear magnetic data is analyzed：1H NMR (400MHz, CDCl3)：δH 7.39
(d, J=7.9Hz, 2H), 7.27 (d, J=8.2Hz, 2H), 7.22-7.15 (m, 4H), 7.07-7.04 (m, 1H), 7.00-6.96
(m, 3H), 6.56 (s, 2H), 6.22 (s, 1H), 3.65 (s, 6H)
13C NMR (100MHz, CDCl3)：δC160.7 (d, J=245.7Hz), 137.5,131.4 (d, J=
14.2Hz), 130.4 (d, J=4.2Hz), 128.3,127.8 (d, J=8.0Hz), 127.4,123.9 (d, J=3.2Hz),
121.6,120.0,118.8,116.9,115.3 (d, J=22.3Hz), 109.2,32.8,32.4 (d, J=4.1Hz)
Embodiment described above is a kind of preferably scheme of the present invention, not makees any formal to the present invention
Limitation, also has other variants and remodeling on the premise of without departing from the technical scheme described in claim.
Claims (10)
1. a kind of diindolylmethane derivative, it is characterised in that shown in its structural formula such as formula (I)：
Wherein, R1For substituted aromatic base or alkyl, R2It is alkoxy, halogen or alkyl；The substituted aromatic base is phenyl, naphthalene
Base, alkyl includes：Methyl, ethyl and cyclohexyl.
2. diindolylmethane derivative according to claim 1, it is characterised in that the substituted aromatic base is phenyl.
3. the preparation method of diindolylmethane derivative described in a kind of claim 1 or 2, it is characterised in that comprise the following steps：
At room temperature, in a nitrogen atmosphere, by the nitrone derivative shown in formula (II), the indole structure compound shown in formula (III)
With the photochemical catalyst dissolving shown in formula (IV) in organic solvent, it is well mixed, is placed in light under blue led s lamps or incandescent lamp
According to a few hours question response it is complete after, solvent is rotated, then through silica gel column chromatography separating purification, you can obtain polysubstituted di-indole methyl hydride
Derivative,
4. the preparation method of diindolylmethane derivative according to claim 3, it is characterised in that shown in the formula (II)
Compound is N- methyl indol compounds.
5. the preparation method of diindolylmethane derivative according to claim 3, it is characterised in that the nitrone derivative,
The molar ratio of indole structure compound and photochemical catalyst is 1: 3: 0.025.
6. the preparation method of diindolylmethane derivative according to claim 3, it is characterised in that the organic solvent is selected from
Dichloromethane, dichloroethanes, acetonitrile or tetrahydrofuran.
7. the preparation method of diindolylmethane derivative according to claim 3, it is characterised in that the throwing of the organic solvent
Material volume is 10-20mL/mmol nitrones.
8. the preparation method of diindolylmethane derivative according to claim 3, it is characterised in that the blue led s lamps
The irradiation reaction time such as (or incandescent lamp other visible light sources) is 12-20h.
9. the preparation method of diindolylmethane derivative according to claim 3, it is characterised in that the silica gel column chromatography point
From the mixed solvent that purifying solvent for use is petroleum ether and ethyl acetate.
10. the preparation method of diindolylmethane derivative according to claim 9, it is characterised in that the petroleum ether and second
The volume ratio of acetoacetic ester is 20-10: 1.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444031A (en) * | 2020-03-25 | 2021-09-28 | 兰州大学 | Synthetic method of 2, 2-diaryl acetonitrile compound |
| CN117384081A (en) * | 2023-10-09 | 2024-01-12 | 上海筛杰生物医药有限公司 | Indolone derivative and preparation method and application thereof |
-
2017
- 2017-06-09 CN CN201710440331.0A patent/CN107235887B/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113444031A (en) * | 2020-03-25 | 2021-09-28 | 兰州大学 | Synthetic method of 2, 2-diaryl acetonitrile compound |
| CN113444031B (en) * | 2020-03-25 | 2023-03-03 | 兰州大学 | Synthesis method of 2, 2-diaryl acetonitrile compound |
| CN117384081A (en) * | 2023-10-09 | 2024-01-12 | 上海筛杰生物医药有限公司 | Indolone derivative and preparation method and application thereof |
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