CN102399168A - Cu (II) coordination compound of Schiff base, preparation method, and application thereof - Google Patents
Cu (II) coordination compound of Schiff base, preparation method, and application thereof Download PDFInfo
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- 0 C1*2=Cc(c(cccc3)c3cc3)c3O[Cn]22Oc3ccc(cccc4)c4c3C=*2CCOCCOC1 Chemical compound C1*2=Cc(c(cccc3)c3cc3)c3O[Cn]22Oc3ccc(cccc4)c4c3C=*2CCOCCOC1 0.000 description 1
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Abstract
The present invention discloses a Cu (II) coordination compound of a Schiff base, wherein the structural formula of the compound is as follow. The preparation method for the compound comprises: adding ethylene glycol-bis-2-aminoethyl ether, 2-hydroxy-1-naphthaldehyde, and a mixed solution comprising methanol and dichloromethane to a reactor, and uniformly mixing; adding an anhydrous methanol solution of Cu(CH3CO2)2.H2O in a dropwise manner while stirring; carrying out stirring for 4-5 hours at a room temperature; carrying out filtering, carrying out drying for the filtrate by evaporation; dissolving the resulting solid by a mixed solvent comprising anhydrous methanol and ethanol, and naturally volatilizing the resulting solution to obtain dark green bulk crystal, wherein the crystal is the Cu (II) coordination compound of the Schiff base. The Cu (II) coordination compound of the Schiff base has high anticancer activity, and can be adopted as the raw material to prepare drugs for treatments of human liver cancer and human chronic myeloid primary leukemia. Compared to the generally-used platinum anticancer drug and the 5-fluorouracil anticancer drug, the compound of the present invention has characteristics of high anticancer activity, low production cost, good lipid solubility and good stability, simple preparation method, no pollution to the environment during the preparation process, high product yield and the like.
Description
Technical field
The present invention relates to a kind of Schiff alkali Cu (II) coordination compound with antitumour activity, and preparation method thereof, and the application in the preparation cancer therapy drug.
Background technology
Schiff alkali is one type and contains carbon-to-nitrogen double bon (RC=N-) the high-performance organic ligand of functional group, this part majority are to be ligating atom with nitrogen-atoms and Sauerstoffatom, and this and coenocorrelation are comparatively approaching, so enjoy people's extensive concern.Result of study shows that Schiff alkali can prepare the Schiff alkali metal complex of novel structure, unique properties with multiple metal-complexing, and its metal complexes all is widely used in fields such as medicine, catalysis, burn into agricultural chemicals, photochromic, novel materials.The research that is used for tumour for metal complexes started from for 16th century; After reported first cis-platinum in 1969 has anti-tumor activity; Metal and metal complex thereof are developed rapidly in pharmaceutically this research field of application, and the metal current coordination compound becomes one of field comparatively active in the antitumor drug research gradually.
Summary of the invention
To above-mentioned prior art, the invention provides a kind of Schiff alkali Cu (II) coordination compound, and preparation method thereof, and its application in the preparation cancer therapy drug is disclosed.
The present invention realizes through following technical scheme:
A kind of Schiff alkali Cu (II) coordination compound, its structural formula is following:
The preparation method of described Schiff alkali Cu (II) coordination compound is: in reactor drum, add ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde and methyl alcohol and methylene dichloride mixed solution, mixing under agitation drips Cu (CH
3CO
2)
2H
2The absolute methanol solution of O, stirring at room 4～5 hours is filtered; The filtrating evaporate to dryness dissolves resulting solid with anhydrous methanol and alcohol mixed solvent, and solution volatilizees naturally; Get the deep green bulk crystals; Be Schiff alkali Cu of the present invention (II) coordination compound, belong to oblique system, spacer is P2 (1)/n.
Said ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde and Cu (CH
3CO
2)
2H
2O is a reactant, and methyl alcohol and methylene dichloride mixed solution are reaction solvent, and anhydrous methanol and alcoholic acid mixture are that solvent is used in crystallization;
Said reactant ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde and Cu (CH
3CO
2)
2H
2The ratio of O three's amount of substance is (1～1.5): 2: (1～1.5), preferred 1: 2: 1.
In said methyl alcohol and the methylene dichloride mixed solution, the volume ratio of methyl alcohol and methylene dichloride is 1: (1～2), preferred 1: 1, total consumption of reaction solvent methyl alcohol and methylene dichloride mixed solution was reactant ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde, Cu (CH
3CO
2)
2 H
220～23 times of O three's total mass;
Said Cu (CH
3CO
2)
2H
2In the absolute methanol solution of O, Cu (CH
3CO
2)
2H
2The concentration of O is 14.98～19.97g/L;
In the mixed solvent that said anhydrous methanol and ethanol are formed, anhydrous methanol and alcoholic acid volume ratio are (1～1.5): 1.
Said filtrating evaporate to dryness adopts Rotary Evaporators.
Said room temperature is meant 20～25 ℃.
The fusing point of Schiff alkali Cu of the present invention (II) coordination compound is 140～143 ℃, and when adopting method for preparing, productive rate is 77～80%.Product is through IR spectroscopy and ultimate analysis, and the result is following:
IR (KBr compressing tablet, cm
-1): 3434 (OH), 1631 (C=N), 1543,1384 (ph-), 1263,1123 (Ph-O), 570 (Cu-N), 448 (Cu-O).
Ultimate analysis C
56H
56Cu
2N
4O
10(M=1072.44), calculated value: C 62.73, H 5.26, and N 5.26%; Experimental value: C 62.62, H 5.19, and N 5.31%.
Crystallographic data: crystallographic system belongs to oblique system, and spacer is P2 (1)/n, and unit cell parameters does
α=90 °, β=110.4510 (10) °, γ=90 °,
Z=4, D=1.404g.cm
-3, F (000)=2233, the crystalline size size is 0.42 * 0.23 * 0.14mm, independent point diffraction: 8907.
Schiff alkali Cu of the present invention (II) coordination compound is that two Sauerstoffatoms in the Schiff aar ligand, two nitrogen-atoms have formed irregular tetrahedral configuration with four-coordination form and Cu (II) ionization, because of the water molecules in the structure cell and intramolecular hydrogen bond exist with dimeric forms.Molecular formula is C
56H
56Cu
2N
4O
10Molecular weight is 1072.44; Have higher anti-cancer activity, and stability is fine, final decomposition temperature is 576.76 ℃; Can it be feedstock production treatment people's liver cancer and the former leukemic medicine of the chronic marrow of people; Compare with the 5 FU 5 fluorouracil anticarcinogen with the platinum class of generally using, Schiff alkali Cu of the present invention (II) coordination compound has the antitumour activity height, production cost is low, fat-soluble and good stability, preparation method are simple, characteristics such as environmentally safe, product yield height in the preparation link, for developing cancer therapy drug new way is provided.
Description of drawings
The hot weightless picture of Schiff alkali Cu (II) coordination compound that Fig. 1 prepares for embodiment 1.
Embodiment
Below in conjunction with embodiment the present invention is further described.
Embodiment 1: preparation Schiff alkali Cu (II) coordination compound
In the 100mL round-bottomed flask, add ethylene glycol bis-2-amino-ethyl ether (0.1482g; 1.0mmol), 2-hydroxyl-1-naphthaldehyde (0.3444g; 2.0mmol) anhydrous methanol and the mixing solutions (15mL of methylene dichloride; Wherein the quality of anhydrous methanol and methylene dichloride is respectively 5.94g and 9.91g), under agitation slowly drip Cu (CH
3CO
2)
2H
2O (0.1997g, absolute methanol solution 1.0mmol) (10mL), stirring at room 4 hours; Filter, the filtrating evaporate to dryness dissolves the solid that obtains with anhydrous methanol and alcohol mixed solvent (anhydrous methanol and alcoholic acid volume ratio are 1: 1); Solution volatilizees naturally, gets the deep green bulk crystals, is Schiff alkali Cu of the present invention (II) coordination compound; Productive rate 77.3%, fusing point: 141～143 ℃.
Product is through IR spectroscopy and ultimate analysis, and the result is following:
IR (KBr compressing tablet, cm
-1): 3434 (OH), 1631 (C=N), 1543,1384 (Ph-), 1263,1123 (Ph-O), 570 (Cu-N), 448 (Cu-O).
Ultimate analysis: calculated value C
56H
56Cu
2N
4O
10: calculated value: C 62.73, H 5.26, and N 5.26%; Measured value: C 62.62, H 5.19, and N 5.31%.
Crystallographic data: crystallographic system belongs to oblique system, and spacer is P2 (1)/n, and unit cell parameters does
α=90 °, β=110.4510 (10) °, γ=90 °,
Z=4, D=1.404g.cm
-3, F (000)=2233, the crystalline size size is 0.42 * 0.23 * 0.14mm, independent point diffraction: 8907.
Can confirm that its structural formula is:
Its hot weightless picture is as shown in Figure 1, and visible, its stability is fine, and final decomposition temperature is 576.76 ℃.
Embodiment 2: preparation Schiff alkali Cu (II) coordination compound
In the 100mL round-bottomed flask, add ethylene glycol bis-2-amino-ethyl ether (0.2964g; 2.0mmol) and 2-hydroxyl-1-naphthaldehyde (0.6887g; 4.0mmol) anhydrous methanol and the mixing solutions (20mL of methylene dichloride; Wherein the quality of anhydrous methanol and methylene dichloride is respectively 7.92g and 13.25g), under agitation slowly drip Cu (CH
3CO
2)
2H
2O (0.3993g, absolute methanol solution 2.0mmol) (20mL), stirring at room 5 hours; Filter, the filtrating evaporate to dryness dissolves the solid that obtains with anhydrous methanol and alcohol mixed solvent; Solution volatilizees naturally, gets the deep green bulk crystals, is Schiff alkali Cu of the present invention (II) coordination compound; Productive rate 78.5%, fusing point: 140～143 ℃.
Embodiment 3: preparation Schiff alkali Cu (II) coordination compound
In the 100mL round-bottomed flask, add ethylene glycol bis-2-amino-ethyl ether (0.2964g; 2.0mmol) and 2-hydroxyl-1-naphthaldehyde (0.6887g; 4.0mmol) anhydrous methanol and the mixing solutions (25ml of methylene dichloride; Wherein the quality of anhydrous methanol and methylene dichloride is respectively 9.90g and 16.56g)), under agitation slowly drip Cu (CH
3CO
2)
2H
2O (0.3993g, absolute methanol solution 2.0mmol) (20ml), stirring at room 4.5 hours; Filter, the filtrating evaporate to dryness dissolves resulting solid with anhydrous methanol and alcohol mixed solvent; Solution volatilizees naturally, gets the deep green bulk crystals, is Schiff alkali Cu of the present invention (II) coordination compound; Productive rate 77.8%, fusing point: 141～143 ℃.
Embodiment 4: preparation Schiff alkali Cu (II) coordination compound
(0.4446g, 3.0mmol) (1.0331g, anhydrous methanol 6.0mmol) and the mixing solutions of methylene dichloride (40mL) under agitation slowly drip Cu (CH with 2-hydroxyl-1-naphthaldehyde in the 250mL round-bottomed flask, to add ethylene glycol bis-2-amino-ethyl ether
3CO
2)
2H
2O (0.5990g, absolute methanol solution 3.0mmol) (40mL, wherein the quality of anhydrous methanol and methylene dichloride is respectively 15.84g and 26.50g); Stirring at room 5 hours is filtered, and filtrating is used evaporate to dryness; With the solid that anhydrous methanol and alcohol mixed solvent dissolving obtain, solution volatilizees naturally, gets the deep green bulk crystals; Be Schiff alkali Cu of the present invention (II) coordination compound, productive rate 80.1%, fusing point: 142～143 ℃.
Test Example: Schiff alkali Cu of the present invention (II) coordination compound (embodiment 1 preparation), its external antitumour activity is measured through MTT and two kinds of experimental techniques of SRB and is realized that its principle is:
The MTT analytical method: (4,5-dimethylthiazol-2-yl)-2,5-diphenyl terrazolium bromide is the basis with metabolism reduction 3-; Have the desaturase relevant with NADP in the viable cell plastosome, can yellow MTT be reduced into insoluble hepatic Formazan, dead cell does not have this enzyme; MTT is not reduced, and behind DMSO dissolving Formazan, available ELIASA is measured the optical density(OD) of characteristic wavelength; Carry out relevant data and handle, reach a conclusion.
The SRB analytical method: Sulforhodamine B is a kind of pink protein bound dyestuff; Water soluble; Can combine with the basic aminoacids in the biomacromolecule; It is good linear relationship at the OD of 515nm reading and cell count, but quantitative Analysis goes out the data of medicine dosage and cells involved number.
With the SRB analytical method people's liver cancer Bel-7402 cell strain is analyzed, the K562 cell strain is analyzed, measure its IC with the MTT analytical method
50Value, the result sees table 1, conclusion is: can know that according to data in the table cancer therapy drug of the present invention is to people's liver cancer and the former leukemic external activity IC of the chronic marrow of people
50Value all is lower than the IC of cis-platinum and 5 FU 5 fluorouracil (contrast)
50Value explains that cancer therapy drug of the present invention has than the obvious in-vitro antitumour activity.
Table 1Schiff alkali Cu (II) coordination compound cancer therapy drug external activity test data
| ? | People's liver cancer | The former white blood disease of the chronic marrow of people |
| Sample IC 50(μM) | 6.880 | 4.454 |
| DDP?IC 50(μM) | 7.7 [1] | 9.3 [2] |
| 5-FU?IC 50(μM) | 23.7 [3] | 65.2 [4] |
| Method | SRB | MTT |
| Cell strain | Bel-7402 | K562 |
Reference: [1] Li Fenghua, Lin Huakuan, Qingdao University of Science and Technology's journal (natural science edition), 2009,30 (2): 123-127.
[2] money flat interest, Zhu Jie, Liu Zeyuan, Chinese clinical medical research magazine, 2005, (137): 14795-14796.
[3] Meng Xiaoyan, Fang Fanfu, Gu Wei, Shandong medicine, 2007,49 (5): 37-39.
[4] Ni Zhenjie, Xue Sijia, the king waits quietly, organic chemistry, 2011,31 (2): 222-226.
Claims (5)
1. a Schiff alkali Cu (II) coordination compound is characterized in that its structural formula is following:
2. the preparation method of the described a kind of Schiff alkali Cu of claim 1 (II) coordination compound; It is characterized in that: in reactor drum, add ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde and methyl alcohol and methylene dichloride mixed solution; Mixing under agitation drips Cu (CH
3CO
2)
2H
2Stirred under the absolute methanol solution of O, room temperature 4～5 hours, and filtered; The filtrating evaporate to dryness, the mixed solvent of forming with anhydrous methanol and ethanol dissolves resulting green solid, naturally volatilization; Get the deep green bulk crystals, be Schiff alkali Cu of the present invention (II) coordination compound;
Wherein, said ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde and Cu (CH
3CO
2)
2H
2The ratio of O three's amount of substance is (1～1.5): 2: (1～1.5);
In said methyl alcohol and the methylene dichloride mixed solution, the volume ratio of methyl alcohol and methylene dichloride is 1: (1～2), total consumption of reaction solvent methyl alcohol and methylene dichloride mixed solution are ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde and Cu (CH
3CO
2)
2H
220～23 times of O three's total mass;
Said Cu (CH
3CO
2)
2H
2In the absolute methanol solution of O, Cu (CH
3CO
2)
2H
2The concentration of O is 14.98～19.97g/L;
In the mixed solvent that said anhydrous methanol and ethanol are formed, anhydrous methanol and alcoholic acid volume ratio are (1～1.5): 1.
3. preparation method according to claim 2 is characterized in that: said ethylene glycol bis-2-amino-ethyl ether, 2-hydroxyl-1-naphthaldehyde and Cu (CH
3CO
2)
2H
2The ratio of O three's amount of substance is 1: 2: 1.
4. preparation method according to claim 2 is characterized in that: said filtrating evaporate to dryness adopts Rotary Evaporators.
5. the application of the described a kind of Schiff alkali Cu of claim 1 (II) coordination compound in preparation treatment people's liver cancer or the former leukemia medicament of the chronic marrow of people.
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| CN103483518A (en) * | 2013-10-11 | 2014-01-01 | 南昌航空大学 | (R)-1,2-propane diamine chiral poly(Schiff base) silver complex material |
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| CN104910042B (en) * | 2015-04-16 | 2017-03-01 | 聊城大学 | A kind of Hydroxynaphthaldehyde manganese complex and preparation method and application |
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