CN100558736C - One nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative and its production and application - Google Patents
One nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative and its production and application Download PDFInfo
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- CN100558736C CN100558736C CNB2007100394677A CN200710039467A CN100558736C CN 100558736 C CN100558736 C CN 100558736C CN B2007100394677 A CNB2007100394677 A CN B2007100394677A CN 200710039467 A CN200710039467 A CN 200710039467A CN 100558736 C CN100558736 C CN 100558736C
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Abstract
The invention discloses a class and have the active nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative of the leukemia K 562 cell line proliferation of inhibition, represent with following general formula: the position of nitro can be the ortho position in the formula, a position, contraposition, R represents methyl, methoxyl group, ethyl etc.
Description
Technical field
The present invention relates to nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative and preparation method thereof and its application on inhibition leukemia K 562 cell line proliferation activity.
Background technology
The polyacid nano-cluster is a kind of pure substance nanoparticle, can assemble and chemically modified it easily, thereby regulate and control its structure and properties effectively.
According to the literature, six molybdate nano-clusters have anti-tumor activity.In order to seek the novel medicine with anti-tumor activity, the present invention selects six molybdate nano-clusters as research object, and design synthesizes a series of nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivatives.Wish to seek a kind of nano level lead compound of novel hybrid with anti-tumor activity.
Summary of the invention
The objective of the invention is for a kind of active nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative of the leukemia K 562 cell line proliferation of inhibition that has is provided.
Another object of the present invention is for the preparation method of this derivative is provided.
Purpose of the present invention can be achieved through the following technical solutions:
A kind of have suppress the active nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative of leukemia K 562 cell line proliferation, with general formula (I) expression:
In the formula:
R＝H，2-CH
3，3-CH
3，2-OCH
3，2-C
2H
5，2，6-CH
3(2)
The position of nitro can be ortho position, a position or contraposition.
Mtt assay (four tell the salt colorimetry) by zooblast-Molecular Biology Lab's standard is measured, and a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative has the leukemia K 562 of inhibition cell line proliferation activity; Can determine the structure of a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative by the X-single crystal diffraction.
A nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative of the present invention includes:
The 2-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
The 3-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
The 4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2-methyl-3-nitro aromatic imine substituted hexamolybdic acid tetrabutylamine
2-methyl-4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2-methyl-5-nitro aromatic imine substituted hexamolybdic acid tetrabutylamine
3-methyl-2-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
3-methyl-4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
3-methyl-5-nitro aromatic imine substituted hexamolybdic acid tetrabutylamine
2-methoxyl group-3-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2-methoxyl group-4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2-methoxyl group-5-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2-ethyl-3-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2-ethyl-4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2-ethyl-5-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2,6-dimethyl-3-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
2,6-dimethyl-4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine
Nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative with general formula (I) expression can prepare with the following method:
Is raw material with eight molybdic acids and general formula for the substituted aniline hydrochloride of (II), in the presence of dewatering agent dicyclohexyl carbodiimide (DCC), refluxes in acetonitrile solution 7～9 hours, obtains the compound that general formula (I) is represented.
R＝H，2-CH
3，3-CH
3，2-OCH
3，2-C
2H
5，2，6-dimethyl
The used dewatering agent of this step is dicyclohexyl carbodiimide (DCC).
Used formula (II) compound and the mol ratio of eight molybdic acids and DCC are 1: 1: 2～1: 2: 3 in this step, and preferred proportion is 1: 1.5: 2.5.
The preparation method of substituted aniline hydrochloride is that substituted aniline and ethanol mix, heating for dissolving, add again concentrated hydrochloric acid to the pH value of solution to acidity, cooling has a large amount of precipitations to separate out, i.e. the compound of general formula (II) expression.
Reaction is what to carry out under the reflux temperature of acetonitrile solvent in this step, and the reaction times is 7～9 hours, and the preferred time is 8 hours.Desolventizing after reaction is finished filters, washing, recrystallization.
Target compound of the present invention (I) adopts the X-single crystal diffraction to determine its structure.
Description of drawings
Fig. 1 is the single crystal structure figure of the embodiment of the invention 1;
Fig. 2 is the single crystal structure figure of the embodiment of the invention 2;
Fig. 3 is the single crystal structure figure of the embodiment of the invention 3;
Embodiment
Further specify technical characterstic of the present invention below in conjunction with embodiment:
Embodiments of the invention are selected for use following derivative to carry out emphasis as representative and are set forth:
2-methyl-4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine (Ia)
2-methyl-5-nitro aromatic imine substituted hexamolybdic acid tetrabutylamine (Ib)
3-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine (Ic)
Embodiment 1: preparation 2-methyl-4-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine (Ia)
With (Bu
4N)
4[α-Mo
8O
26] (1.0mmol), DCC (2.5mmol) and 2-methyl-4-N-methyl-p-nitroaniline hydrochloride (1.5mmol) is mixed in anhydrous acetonitrile (15ml), refluxes and stirs 8 hours, has a large amount of white precipitates to generate and dark red solution.Stopped reaction is cooled to room temperature, removes by filter white precipitate, places dark red filtrate, treats that acetonitrile slowly volatilizees to finish, and obtains the red solid of colloidal.Obtain afterwards orange crystal twice with acetone and alcoholic acid mixing solutions (30ml, 1: 1.5) recrystallization.Productive rate: 60%
Ultimate analysis: measured value (%) C, 31.24; H, 5.21; N, 3.74.
Calculated value (%) C, 31.26; H, 5.25; N, 3.74.
IR (the KBr compressing tablet, cm-1): 2962,2868,1597,1573,1516,1483,1381,1319,1147,976,957,882,790.
1H?NMR(δ，ppm，CD
3CN)：0.98(t，24H，-CH
3，[Bu
4N]
+)，1.38(m，16H，-CH
2-，[Bu
4N]
+)，1.65(m，16H，-CH
2-，[Bu
4N]
+)，3.14(m，16H，-CH
2-，[Bu
4N]
+)，2.68(s，3H，Ar-CH
3)，7.30-8.15(m，3H，ArH).
Single crystal structure figure as shown in Figure 1.
The single crystal structure data:
Empirical?formula?C39H78Mo6N4O20
Formula?weight 1498.69
Temperature 297(2)K
Wavelength 0.71073
Crystal?system Monoclinic
Space?group P2
1/c
Unit?cell?dimensions?a＝16.6532(9)
b＝16.7588(9)
c＝20.2461(11)
α＝90°
β＝91.0320(10)°
γ＝90°
Volume5649.5(5)
Density(calculated) 1.762Mg/m
3
Absorption?coefficient 1.361mm
-1
F(000)3008
Crystal?size?0.20?x?0.20?x?0.10mm
3
Theta?range?for?data?collection 1.58?to?26.00°.
Index?ranges -20＜＝h＜＝20，-20＜＝k＜＝20，-24＜＝l＜＝24
Reflections?collected?57534
Independent?reflections?11097[R(int)＝0.0287]
Completeness?to?theta＝26.00 99.9％
Absorption?correction?None
Max.and?min.transmission?0.8759and?0.7725
Refinement?method?Full-matrix?least-squares?on?F
2
Data/restraints/parameters?11097/67/688
Goodness-of-fit?on?F
2?1.110
Final?R?indices[I＞2sigma(I)]R1＝0.0671，wR2＝0.2057
R?indices(all?data)R1＝0.0881，wR2＝0.2251
Largest?diff.peak?and?hole 2.267and-0.658e.
Embodiment 2: preparation 2-methyl-5-nitro aromatic imine substituted hexamolybdic acid tetrabutylamine (Ib)
With (Bu
4N)
4[α-Mo
8O
26] (1.0mmol), DCC (2.5mmol) and 2-methyl-5-nitro anilinechloride (1.5mmol) are mixed in anhydrous acetonitrile (15ml), reflux and stir 8 hours, have a large amount of white precipitates to generate and dark red solution.Stopped reaction is cooled to room temperature, removes by filter white precipitate, places dark red filtrate, treats that acetonitrile slowly volatilizees to finish, and obtains the red solid of colloidal.Obtain afterwards orange crystal twice with acetone and alcoholic acid mixing solutions (30ml, 1: 1.5) recrystallization.Productive rate: 56%
Ultimate analysis: measured value (%) C, 31.24; H, 5.21; N, 3.74.
Calculated value (%) C, 31.26; H, 5.25; N, 3.74.
IR (the KBr compressing tablet, cm-1): 2958,2872,1491,1466,1373,1334,1225,1140,976,956,882,796.
1H?NMR(δ，ppm，CD
3CN)：1.02(t，24H，-CH
3，[Bu
4N]
+)，1.43(m，16H，-CH
2-，[Bu
4N]
+)，1.69(m，16H，-CH
2-，[Bu
4N]
+)，3.18(m，16H，-CH
2-，[Bu
4N]
+)，2.73(s，3H，Ar-CH
3)，7.50-7.93(m，3H，ArH)
Single crystal structure figure as shown in Figure 2.
The single crystal structure data:
Empirical?formula C39H78Mo6N4O20
Formula?weight 1498.69
Temperature 297(2)K
Wavelength 0.71073
Crystal?system Monoclinic
Space?group P2
1/c
Unit?celldimensions?a＝12.4519(7)
b＝19.5005(11)
c＝23.6287(14)
α＝90°
β＝92.0620(10)°
γ＝90°
Volume5733.8(6)
Density(calculated) 1.736Mg/m
3
Absorption?coefficient 1.341mm
-1
F(000)3008
Crystal?size?0.30?x?0.30?x?0.20mm
3
θrange?for?data?collection?1.35-27.00°.
Index?ranges -15＜＝h＜＝15，-24＜＝k＜＝24，-30＜＝l＜＝29
Reflections?collected?47475
Independent?reflections?12490[R(int)＝0.0241]
Completeness?to?theta＝27.00?99.8％
Absorption?correction?None
Max.and?min.transmission?0.7752?and?0.6891
Refinement?method?Full-matrix?least-squares?on?F
2
Data/restraints/parameters?12490/44/659
Goodness-of-fit?on?F
2 1.036
Final?R?indices[I＞2sigma(I)]R1＝0.0392，wR2＝0.1022
R?indices(all?data)R1＝0.0548，wR2＝0.1129
Largest?diff.peak?and?hole?0.728?and-0.493e.
Embodiment 3: preparation 3-nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine (Ic)
With (Bu
4N)
4[α-Mo
8O
26] (1.0mmol), DCC (2.5mmol) and 3-N-methyl-p-nitroaniline hydrochloride (1.5mmol) are mixed in anhydrous acetonitrile (15ml), reflux and stir 8 hours, have a large amount of white precipitates to generate and dark red solution.Stopped reaction is cooled to room temperature, removes by filter white precipitate, places dark red filtrate, treats that acetonitrile slowly volatilizees to finish, and obtains the red solid of colloidal.Obtain afterwards orange crystal twice with acetone and alcoholic acid mixing solutions (30ml, 1: 1.5) recrystallization.Productive rate: 58%
Ultimate analysis: measured value (%) C, 30.73; H, 5.12; N, 3.78.
Calculated value (%) C, 31.26; H, 5.25; N, 3.74.
IR (the KBr compressing tablet, cm-1): 2962,2868,1597,1573,1516,1483,1381,1319,1147,976,957,882,790.
1H?NMR(δ，ppm，CD
3CN)：1.02(t，24H，-CH
3，[Bu
4N]
+)，1.42(m，16H，-CH
2-，[Bu
4N]
+)，1.69(m，16H，-CH
2-，[Bu
4N]
+)，3.20(m，16H，-CH
2-，[Bu
4N]
+)，7.60-8.06(m，3H，ArH)
Single crystal structure figure is as shown in Figure 3:
The single crystal structure data:
Identification?code 061114
Empirical?formula C38H76Mo6N4O20
Formula?weight 1484.67
Temperature 297(2)K
Wavelength 0.71073
Crystal?system monoclinic
Space?group P2
1/c
Unit?cell?dimensions?a＝16.8273(17)
b＝17.3291(17)
c＝19.685(2)
α＝90°.
β＝91.057(2)°.
γ＝90°.
Volume5739.1(10)
Density(calculated) 1.718Mg/m
3
Absorption?coefficient 1.339mm
-1
F(000)2976
Crystal?size?0.20?x?0.10?x?0.10mm
3
Theta?range?for?data?collection?1.2l?to?25.00°.
Index?ranges -20＜＝h＜＝20，-20＜＝k＜＝20，-23＜＝l＜＝23
Reflections?collected?39217
Independent?reflections?10101[R(int)＝0.0640]
Completeness?to?theta＝25.00°100.0％
Max.and?min.transmission?0.8777?and?0.7755
Refinement?method?Full-matrix?least-squares?on?F
2
Data/restraints/parameters?10101/566/613
Goodness-of-fit?on?F
2 1.194
Final?R?indices[I＞2sigma(I)]R1＝0.0790，wR2＝0.1384
R?indices(all?data)R1＝0.1363，wR2＝0.1565
Largest?diff.peak?and?hole?0.589and-0.609e.
Suppress leukemia K 562 cell line proliferation determination of activity experiment
Adopt the mtt assay (four tell the salt colorimetry) of Shanghai Normal University's zooblast-Molecular Biology Lab's standard to measure, adopt 5-Fu as the positive control data.
Test materials and content:
Examination material: human leukemia K562 cell
Experimental technique: mtt assay
Experimental temperature: 37 ℃
Experimental period: 2007.03.05-2007.03.12
Part of compounds suppresses leukemia K 562 cell line proliferation active testing data and sees Table 1.
Table 1. part of compounds suppresses leukemia K 562 cell line proliferation active testing data
By above data as can be seen: a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative has the leukemia K 562 of inhibition cell line proliferation activity.
Claims (9)
1, a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative, represent with general formula (I):
In the formula:
R＝H，2-CH
3，3-CH
3，2-OCH
3，2-C
2H
5，2，6-CH
3(2)
The position of nitro is ortho position, a position or contraposition.
2, the preparation method of the nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative in the claim 1 is as follows:
Is raw material with eight molybdic acids and general formula for the substituted aniline hydrochloride of (II), in the presence of dewatering agent, refluxes in acetonitrile solution 7～9 hours, obtains the compound that general formula (I) is represented:
R＝H，2-CH
3，3-CH
3，2-OCH
3，2-C
2H
5，2，6-dimethyl。
3, the preparation method of a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative according to claim 2 is characterized in that: described dewatering agent is a dicyclohexyl carbodiimide.
4, the preparation method of a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative according to claim 2 is characterized in that: the mol ratio of compound, eight molybdic acids and three kinds of materials of DCC that formula (II) is represented is 1: 1: 2～1: 2: 3.
5, the preparation method of a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative according to claim 4 is characterized in that: the mol ratio of compound, eight molybdic acids and three kinds of materials of DCC that formula (II) is represented is 1: 1.5: 2.5.
6, the preparation method of a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative according to claim 2, it is characterized in that: the preparation method of described substituted aniline hydrochloride is: substituted aniline and ethanol mix, heating for dissolving, add again concentrated hydrochloric acid to the pH value of solution to acidity, cooling, there are a large amount of precipitations to separate out, i.e. the compound of general formula (II) expression.
7, the preparation method of a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative according to claim 2 is characterized in that: entire reaction is to carry out under the reflux temperature of acetonitrile solvent, and the reaction times is 7～9 hours.
8, the preparation method of a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative according to claim 7 is characterized in that: entire reaction is to carry out under the reflux temperature of acetonitrile solvent, and the reaction times is 8 hours.
9, a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative according to claim 1 is characterized in that: a nitryl aromatic imine substituted hexamolybdic acid tetrabutylamine derivative has the leukemia K 562 of inhibition cell line proliferation activity.
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Non-Patent Citations (4)
| Title |
|---|
| Organic-inorganic hybrids:preparation and structuralcharacterization of (Bu4N)2[Mo6O17(NAr)2] and(Bu4N)2[Mo6O17(NAr)](Ar=o-CH3C6H4). Qiang Li etal.Anorg allg chem,No.631. 2005 |
| Organic-inorganic hybrids:preparation and structuralcharacterization of (Bu4N)2[Mo6O17(NAr)2] and(Bu4N)2[Mo6O17(NAr)](Ar=o-CH3C6H4). Qiang Li etal.Anorg allg chem,No.631. 2005 * |
| synthesis,spectroscopic studies and crystal structure of apolyoxoanion cluster incorporatiing para-bromophenylimidoligand,(Bu4N)2[Mo6O18(NC6H4Br-p)]. Qiang Li etal.Journal of organometallic chemistry,No.691. 2006 |
| synthesis,spectroscopic studies and crystal structure of apolyoxoanion cluster incorporatiing para-bromophenylimidoligand,(Bu4N)2[Mo6O18(NC6H4Br-p)]. Qiang Li etal.Journal of organometallic chemistry,No.691. 2006 * |
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