CN105315310B - A kind of nickel complex of contracted containing 3,5 dichloro-salicylaldehydes 4 chlorine o-aminophenol Schiffs and pyridine and its preparation method and application - Google Patents
A kind of nickel complex of contracted containing 3,5 dichloro-salicylaldehydes 4 chlorine o-aminophenol Schiffs and pyridine and its preparation method and application Download PDFInfo
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- CN105315310B CN105315310B CN201510650241.5A CN201510650241A CN105315310B CN 105315310 B CN105315310 B CN 105315310B CN 201510650241 A CN201510650241 A CN 201510650241A CN 105315310 B CN105315310 B CN 105315310B
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Abstract
The invention discloses the nickel complex that one kind contains 3,5 dichloro-salicylaldehydes, 4 chlorine o-aminophenol Schiffs of contracting and pyridine, for the complex of following structure formula (I).The invention also discloses the preparation method of the nickel complex for containing 3,5 dichloro-salicylaldehydes, 4 chlorine o-aminophenol Schiffs of contracting and pyridine and the application in cancer therapy drug is prepared.
Description
Technical field
Coordinate the present invention relates to a kind of containing the nickel of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Thing and preparation method thereof, and this contains the nickel complex of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Application in cancer therapy drug is prepared.
Background technology
Schiff is primarily referred to as containing imines or azomethine characteristic group（-RC=N-）A kind of organic compound, closing
Have synthesis cycle short into upper, the features such as operating method simplicity and there is good coordination with metal ion.Schiff
The research of alkali metal complex starts from 20th century the fifties, is widely used in antibacterial and antitumor work because of its unique structure
Journal of Sex Research, suppress superoxide radical activity, chemical analysis and with the many-side such as DNA interaction, especially its have
Stronger antibacterial, anticancer bioactive, this causes people increasingly to pay close attention to the biological medical value of this kind of complex.For example,
Hodnett seminars were found that the organic coordination compound containing Schiff has certain antitumor activity in 1970, also,
Active anticancer strengthens after it and part metals ion form complex.
Document (chemical reagent, 2013,35 (11):1023-1027) report, a kind of Amino Acid Schiff Bases and its copper,
The synthesis of nickel complex and bacteriostatic activity.
Document (chemical reagent, 2003,25 (5):274-276) report, the active anticancer of Schiff metal complex
Progress.
Document (Inorganic Chemistry Communications, 2015,57:8-10) report, transition metal
Cu（II）、Cd（II）、Zn（II）Shciff alkali complexs are to human lung adenocarcinoma cell（A549）, gastric carcinoma cells（BGC-823 and
SGC-7901）All there is good inhibiting effect.
Document (Journal of Molecular Strcture, 2013,1049:326-335) report, Cu（II）
Shciff alkali complexs are to human breast cancer cell（MCF7）, human liver cancer cell（HepG2）, human colon cancer cell（HCT-116）
Inhibitory activity order be：MCF7 ＞ HCT-116 ＞ HepG2.
It is that the experiment proved that the material with active anticancer based on Schiff metal complex, present invention selection 3,5- bis-
Chloro-salicylic aldehyde's contracting 4- chlorine o-aminophenol Schiffs and pyridine are part, are reacted under certain condition with nickel acetate, synthesis obtains
To human colon cancer cell（Colo205）, human liver cancer cell（HepG2）, human breast cancer cell（MCF7）It is thin with human cervical carcinoma
Born of the same parents（Hela）Complex with certain inhibitory activity, new approach is provided for exploitation cancer therapy drug.
The content of the invention
The first object of the present invention there is provided one kind and contain 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenol Schiffs
With the nickel complex of pyridine.
The second object of the present invention be to provide it is above-mentioned containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs with
The nickel complex preparation method of pyridine.
The third object of the present invention be to provide it is above-mentioned containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs with
Application of the nickel complex of pyridine in cancer therapy drug is prepared.
One kind as the first aspect of the present invention contain 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs with
The nickel complex of pyridine, it is the complex of structure formula (I)
(I)。
The nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention is through member
Element analysis, infrared spectrum and X-ray single crystal diffraction structural analysis, it is as a result as follows：
Elementary analysis (C28H21Cl3N4O2Ni)：Calculated value：C 55.08, H 3.47, N 9.18；Measured value：C 55.04, H
3.52, N 9.23.
FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209,
1037。
The nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention is crystalline substance
Body structure, its crystal are anorthic system, space group P-1, a=0.8972 (4) nm, b=0.9010 (4) nm, c=
1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10)
nm3。
The knot of the nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention
Structure feature is：Nickle atom is the distorted octahedron configuration of hexa-coordinate in molecule.
One kind as the second aspect of the present invention contain 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs with
The preparation method of the nickel complex of pyridine, it is that 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols Schiff is added in reaction vessel
Alkali and solvent absolute ethyl alcohol, the ethanol solution of 50 mmol/L nickel acetate is instilled after heating for dissolving, be stirred at reflux lower reaction 5
~11 h, are then added dropwise pyridine, continue the h of backflow 5~15, cool down, filtering, control solvent volatilization crystallization, obtain amber transparent crystalline substance
Body, as contain the nickel complex of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.
In a preferred embodiment of the invention, 3, the 5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs with
The amount ratio of the material of nickel acetate is 1:1~1:1.2.
In a preferred embodiment of the invention, the dosage of the solvent absolute ethyl alcohol is every mM 3, the chlorine waters of 5- bis-
Poplar aldehyde contracting 4- chlorine o-aminophenol Schiffs add 12~24 milliliters.
In a preferred embodiment of the invention, the dosage of the pyridine is every mM 3,5- dichloro-salicylaldehyde's contractings 4-
14~28 milliliters of chlorine o-aminophenol Schiff.
One kind as the third aspect of the present invention contain 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs with
Application of the nickel complex of pyridine in cancer therapy drug is prepared.
Applicant is to the above-mentioned nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Carried out anti tumor activity in vitro determine research, it is thus identified that contain 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and
The nickel complex of pyridine has certain anticancer bioactive, that is to say, that the purposes of above-mentioned complex is to prepare cancer therapy drug
In application, be exactly specifically the application in anti-human colon cancer, human liver cancer, human breast carcinoma, human cervical cancer 1 cancer drug is prepared.
The nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention is to people
Colon cancer cell, human liver cancer cell, human breast cancer cell and human cervical carcinoma cell show good active anticancer, the present invention
The nickel complex active anticancer containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine it is high, cost is low,
The features such as preparation method is simple, the cancer therapy drug to develop new provide new way.
Brief description of the drawings
Fig. 1 is that the IR of the nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine is composed
Figure.
Fig. 2 is the crystal knot of the nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Composition.
Fig. 3 is the TG-DTG of the nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Curve.
Embodiment
The present invention is further described by following examples, but should be noted that the scope of the present invention is not implemented by these
Any restrictions of example.
Embodiment 1：
The preparation of nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
0.314 g (1.0 mmol) 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols are added in 100mL three-necked flasks
Schiff and 15mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 20mL 50 nickel acetate is instilled after heating for dissolving,
5 h of lower reaction are stirred at reflux, 14mL pyridines are then added dropwise, continue 8 h that flow back, are cooled down, filtering, control solvent volatilization crystallization, are obtained
Amber transparent crystal, as contain the nickel complex of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Production
Rate：83.7%.Fusing point：93~94 DEG C (dec).
Elementary analysis (C28H21Cl3N4O2Ni)：Calculated value：C 55.08, H 3.47, N 9.18；Measured value：C 55.04, H
3.52, N 9.23.
FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209,
1037。
Crystallographic data：Anorthic system, space group P-1, a=0.8972 (4) nm, b=0.9010 (4) nm, c=
1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10)
nm3。
Embodiment 2：
The preparation of nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
0.314 g (1.0 mmol) 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols are added in 100mL three-necked flasks
Schiff and 12mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 22mL 50 nickel acetate is instilled after heating for dissolving,
8 h of lower reaction are stirred at reflux, 18mL pyridines are then added dropwise, continue 5 h that flow back, are cooled down, filtering, control solvent volatilization crystallization, are obtained
Amber transparent crystal, as contain the nickel complex of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Production
Rate：85.1%.Fusing point：93~94 DEG C (dec).
Elementary analysis (C28H21Cl3N4O2Ni)：Calculated value：C 55.08, H 3.47, N 9.18；Measured value：C 55.04, H
3.52, N 9.23.
FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209,
1037。
Crystallographic data：Anorthic system, space group P-1, a=0.8972 (4) nm, b=0.9010 (4) nm, c=
1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10)
nm3。
Embodiment 3：
The preparation of nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
0.314 g (1.0 mmol) 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols are added in 100mL three-necked flasks
Schiff and 20mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 24mL 50 nickel acetate is instilled after heating for dissolving,
9 h of lower reaction are stirred at reflux, 28mL pyridines are then added dropwise, continue 13 h that flow back, are cooled down, filtering, control solvent volatilization crystallization, are obtained
Amber transparent crystal, as contain the nickel complex of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Production
Rate：85.0%.Fusing point：93~94 DEG C (dec).
Elementary analysis (C28H21Cl3N4O2Ni)：Calculated value：C 55.08, H 3.47, N 9.18；Measured value：C 55.04, H
3.52, N 9.23.
FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209,
1037。
Crystallographic data：Anorthic system, space group P-1, a=0.8972 (4) nm, b=0.9010 (4) nm, c=
1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10)
nm3。
Embodiment 4：
The preparation of nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
1.570 g (5.0 mmol) 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols are added in 500mL three-necked flasks
Schiff and 90 mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 110mL 50 nickel acetate is instilled after heating for dissolving,
7 h of lower reaction are being stirred at reflux, 90mL pyridines are then added dropwise, are continuing 9 h that flow back, are being cooled down, filtering, control solvent volatilization crystallization,
Amber transparent crystal is obtained, as contains the nickel complex of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.
Yield：80.6%.Fusing point：93~94 DEG C (dec).
Elementary analysis (C28H21Cl3N4O2Ni)：Calculated value：C 55.08, H 3.47, N 9.18；Measured value：C 55.04, H
3.52, N 9.23.
FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209,
1037。
Crystallographic data：Anorthic system, space group P-1, a=0.8972 (4) nm, b=0.9010 (4) nm, c=
1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10)
nm3。
Embodiment 5：
The preparation of nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
Middle addition 3.140 g (10.0 mmol) 3,5- dichloro-salicylaldehyde's contracting 4- chlorine neighbour's amino in 1000mL three-necked flasks
Phenol Schiff and 240mL solvent absolute ethyl alcohols, the ethanol that the mmol/L of 210mL 50 nickel acetate is instilled after heating for dissolving are molten
Liquid, 10 h of lower reaction are being stirred at reflux, 220mL pyridines are then added dropwise, continuing 15 h that flow back, cooled down, filtering, control solvent volatilization
Crystallization, obtains amber transparent crystal, the nickel for as containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine is matched somebody with somebody
Compound.Yield：81.2%.Fusing point：93~94 DEG C (dec).
Elementary analysis (C28H21Cl3N4O2Ni)：Calculated value：C 55.08, H 3.47, N 9.18；Measured value：C 55.04, H
3.52, N 9.23.
FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209,
1037。
Crystallographic data：Anorthic system, space group P-1, a=0.8972 (4) nm, b=0.9010 (4) nm, c=
1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10)
nm3。
Embodiment 6：
The preparation of nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
Middle addition 3.140 g (10.0 mmol) 3,5- dichloro-salicylaldehyde's contracting 4- chlorine neighbour's amino in 1000mL three-necked flasks
Phenol Schiff and 160mL solvent absolute ethyl alcohols, the ethanol that the mmol/L of 225mL 50 nickel acetate is instilled after heating for dissolving are molten
Liquid, 11 h of lower reaction are being stirred at reflux, 240mL pyridines are then added dropwise, continuing 11 h that flow back, cooled down, filtering, control solvent volatilization
Crystallization, obtains amber transparent crystal, the nickel for as containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine is matched somebody with somebody
Compound.Yield：79.5%.Fusing point：93~94 DEG C (dec).
Elementary analysis (C28H21Cl3N4O2Ni)：Calculated value：C 55.08, H 3.47, N 9.18；Measured value：C 55.04, H
3.52, N 9.23.
FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209,
1037。
Crystallographic data：Anorthic system, space group P-1, a=0.8972 (4) nm, b=0.9010 (4) nm, c=
1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10)
nm3。
Test example：
The nickel complex for containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention, its body
Outer active anticancer measure is realized by MTT experiment method.
MTT analytic approach：
3- (4,5-Dimethylthiazol-2-yl) -2,5-diphenyltetrazolium is reduced with metabolism
Based on bromide.Succinate dehydrogenase in living cells mitochondria can make exogenous MTT be reduced to the bluish violet of water-insoluble
Crystallize first a ceremonial jade-ladle, used in libation（Formazan）And be deposited in cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO)（DMSO）Cell can be dissolved
In first a ceremonial jade-ladle, used in libation, with ELIASA determine characteristic wavelength optical density, living cells quantity can be reflected indirectly.
Using mtt assay come determine embodiment 1 preparation contain 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenol Schiffs
Nickel complex with pyridine is to human colon cancer cell（Colo205）, human liver cancer cell（HepG2）, human breast cancer cell（MCF7）、
Human cervical carcinoma cell（Hela）And human lung carcinoma cell（NCI-H460）Inhibitory activity.
Cell line and cultivating system：Colo205, HepG2, MCF7, HEK93 and NCI-H460 cell line are derived from American. tissue
Incubator（ATCC）.With the RPMI 1640 containing 10% hyclone（GIBICO companies）Culture medium, 5%（Volume fraction）CO2、
In vitro culture is carried out in 37 DEG C of saturated humidity incubators.
Test process：Decoction will be tested（1ng/mL~100ug/mL）Concentration gradient according to concentration is added separately to each
Kong Zhong, each concentration set 6 parallel holes.Experiment is divided into drug study group（It is separately added into the test medicine of various concentrations）, control group
（Only add nutrient solution and cell, be not added with testing medicine）And blank group（Only plus medicine is cultivated, be not added with cell and test medicine）.After dosing
Orifice plate is placed in 37 DEG C, 5%CO272h is cultivated in incubator.The activity of control drug determines according to the method for test sample.Cultivating
In orifice plate after 72h, add MTT 40uL per hole（4mg/mL is made into D-Hanks buffer solutions）.After 37 DEG C are placed 4h, remove
Supernatant liquor.Add 150uL DMSO per hole, vibrate 5min, make Formazan crystallization dissolvings.Finally, existed using automatic ELIASA
The optical density in each hole is detected at 570nm wavelength.
Data processing：Data processing uses the programs of Graph Pad Prism version 5.0, complex IC50Pass through journey
The nonlinear regression model (NLRM) with S-shaped dose response is fitted to obtain in sequence.
With MTT analytic approach to human colon cancer cell（Colo205）, human liver cancer cell（HepG2）, breast cancer cell
（MCF7）, cervical cancer cell（Hela）And human lung carcinoma cell（NCI-H460）Cell line is analyzed, and determines its IC50Value, knot
Fruit is as shown in table 1, and conclusion is：From data in table, 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols are contained with the present invention
The nickel complex of Schiff and pyridine is used as cancer therapy drug, to human colon cancer cell（Colo205）, human liver cancer cell
（HepG2）, human breast cancer cell（MCF7）And human cervical carcinoma cell（Hela）With certain drug effect, cancer therapy drug can be used as
Candidate compound.
Nickel complex cancer therapy drug of the table 1 containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
External activity test data
Nickel containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine prepared by remaining embodiment is matched somebody with somebody
Compound is with mtt assay to human colon cancer cell（Colo205）, human liver cancer cell（HepG2）, human breast cancer cell（MCF7）, people son
Cervical cancer cell（Hela）And human lung carcinoma cell（NCI-H460）The same test example of active anticancer method of testing, test result and table
1 is essentially identical.
Claims (3)
- It is following structure 1. one kind contains the nickel complex of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine The complex of formula (I)：(I)；Described complex (I) is crystal structure, and its crystallographic data is as follows：Anorthic system, space group P-1, a= 0.8972 (4) nm, b=0.9010 (4) nm, c=1.7574 (8) nm, α=104.410 (5) °, β=92.753 (5) °, γ=100.603 (6) °, Z=2, V=1.3459 (10) nm3；Nickle atom is the distorted octahedron configuration of hexa-coordinate in molecule； The infrared data of described complex (I)：FT-IR (KBr, cm-1): 3066, 3053, 1597, 1571, 1481, 1469, 1319, 1209, 1037；The preparation method of described complex (I), it is characterized in that adding 3,5- in reaction vessel Dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenol Schiffs and solvent absolute ethyl alcohol, 50 mmol/L acetic acid is instilled after heating for dissolving The ethanol solution of nickel, 5~11 h of lower reaction are being stirred at reflux, pyridine is then added dropwise, continues the h of backflow 5~15, cooled down, filtering, Solvent volatilization crystallization is controlled, amber transparent crystal is obtained, as contains 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenol Schiffs With the nickel complex of pyridine；Wherein, the amount of the material of 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and nickel acetate Than for 1:1~1:1.2；The dosage of solvent absolute ethyl alcohol is every mM of 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols Schiff Alkali adds 12~24 milliliters；The dosage of pyridine is every mM of 3,5- dichloro-salicylaldehyde's contracting 4- chlorine o-aminophenols Schiff 14~28 Milliliter；Described complex (I) has certain thermostabilization scope, can be stabilized below 93 DEG C.
- 2. the nickel complex containing 3,5- dichloro-salicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine described in claim 1 exists Prepare the application in cancer therapy drug.
- 3. the application described in claim 2, wherein the cancer cell is that human colon cancer cell, human liver cancer cell, human breast carcinoma are thin Born of the same parents, human cervical carcinoma cell.
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| CN103396436A (en) * | 2013-07-22 | 2013-11-20 | 衡阳师范学院 | Monobutyltin trichloride substituted salicylidenedimine Schiff base complex as well as preparation method and applications thereof |
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| CN103396436A (en) * | 2013-07-22 | 2013-11-20 | 衡阳师范学院 | Monobutyltin trichloride substituted salicylidenedimine Schiff base complex as well as preparation method and applications thereof |
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