CN105315312B - A kind of nickel complex of contracted containing 5 bromosalicylaldehydes 4 chlorine o-aminophenol Schiffs and pyridine and its preparation method and application - Google Patents
A kind of nickel complex of contracted containing 5 bromosalicylaldehydes 4 chlorine o-aminophenol Schiffs and pyridine and its preparation method and application Download PDFInfo
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- CN105315312B CN105315312B CN201510650547.0A CN201510650547A CN105315312B CN 105315312 B CN105315312 B CN 105315312B CN 201510650547 A CN201510650547 A CN 201510650547A CN 105315312 B CN105315312 B CN 105315312B
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Abstract
The invention discloses a kind of nickel complex containing 5 bromosalicylaldehydes, 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 5 bromosalicylaldehydes, 4 chlorine o-aminophenol Schiffs of contracting and pyridine and the application in cancer therapy drug is prepared.
Description
Technical field
The present invention relates to a kind of nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine and
Its preparation method, and be somebody's turn to do the nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine and resist in preparation
Application in cancer drug.
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 5- bromine waters
Poplar aldehyde contracting 4- chlorine o-aminophenol Schiffs and pyridine are part, are reacted under certain condition with nickel acetate, and synthesis has obtained pair
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）Complex with certain inhibitory activity, provided for exploitation cancer therapy drug new
Approach.
The content of the invention
The first object of the present invention there is provided one kind and contain 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyrrole
The nickel complex of pyridine.
The second object of the present invention is to provide above-mentioned containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Nickel complex preparation method.
The third object of the present invention is to provide above-mentioned containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Application of the nickel complex in cancer therapy drug is prepared.
One kind as the first aspect of the present invention contains 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Nickel complex, be structure formula (I) complex
(I)。
The nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention is through element point
Analysis, infrared spectrum and X-ray single crystal diffraction structural analysis, it is as a result as follows：
Elementary analysis (C28H22BrClN4O2Ni)：Calculated value：C 54.19, H 3.57, N 9.03；Measured value：C 54.24,
H 3.52, N 9.06.
FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479, 1442, 1375, 1219,
1070。
The nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention is crystal knot
Structure, its crystal are anorthic system, space group P-1, a=0.89747 (19) nm, b=0.89922 (19) nm, c=
1.7140 (4) nm, α=104.069 (3) °, β=96.547 (2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5)
nm3。
The structure of the nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention is special
Putting is：Nickle atom is the distorted octahedron configuration of hexa-coordinate in molecule.
One kind as the second aspect of the present invention contains 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Nickel complex preparation method, be that 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and solvent are added in reaction vessel
Absolute ethyl alcohol, the ethanol solution of 50 mmol/L nickel acetate is instilled after heating for dissolving, is being stirred at reflux 5~11 h of lower reaction, so
After pyridine is added dropwise, continue the h of backflow 5~15, cool down, filtering, control solvent volatilization crystallization, obtain amber transparent crystal, as contain
The nickel complex of 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.
In a preferred embodiment of the invention, the 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and acetic acid
The amount ratio of the material of nickel is 1:1~1:1.2.
In a preferred embodiment of the invention, the dosage of the solvent absolute ethyl alcohol is every mM of 5- bromosalicylaldehyde
Contracting 4- chlorine o-aminophenol Schiffs add 12~24 milliliters.
In a preferred embodiment of the invention, the dosage of the pyridine is that every mM of 5- bromosalicylaldehyde contracting 4- chlorine is adjacent
14~28 milliliters of amino phenols Schiff.
One kind as the third aspect of the present invention contains 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Application of the nickel complex in cancer therapy drug is prepared.
Applicant is carried out to above-mentioned containing the nickel complex of 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Anti tumor activity in vitro determines research, it is thus identified that nickel containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Complex has certain anticancer bioactive, that is to say, that the purposes of above-mentioned complex is answering in cancer therapy drug is prepared
With, be exactly specifically in anti-human colon cancer, human liver cancer, human breast carcinoma, human cervical carcinoma, human lung cancer medicine is prepared should
With.
The nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention is to people's colon
Cancer cell, human liver cancer cell, human breast cancer cell, human cervical carcinoma cell and human lung carcinoma cell show that good anticancer is lived
Property, it is of the invention containing the nickel complex active anticancer of 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine it is high, into
The features such as this is low, preparation method is simple, the cancer therapy drug to develop new provide new way.
Brief description of the drawings
Fig. 1 is the IR spectrograms of the nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.
Fig. 2 is the crystal structure of the nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Figure.
Fig. 3 is that the TG-DTG of the nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine is bent
Line.
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 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
0.326 g (1.0 mmol) 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols Schiff is added in 100mL three-necked flasks
Alkali and 15mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 20mL 50 nickel acetate is instilled after heating for dissolving, is being stirred back
5 h of reaction are flowed down, 14mL pyridines are then added dropwise, continue 8 h that flow back, are cooled down, filtering, control solvent volatilization crystallization, it is saturating to obtain brown
Bright crystal, the nickel complex as containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Yield：86.7%.It is molten
Point：86~88 DEG C (dec).
Elementary analysis (C28H22BrClN4O2Ni)：Calculated value：C 54.19, H 3.57, N 9.03；Measured value：C 54.24,
H 3.52, N 9.06.
FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479, 1442, 1375, 1219,
1070。
Crystallographic data：Anorthic system, space group P-1, a=0.89747 (19) nm, b=0.89922 (19) nm, c
=1.7140 (4) nm, α=104.069 (3) °, β=96.547 (2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5)
nm3。
Embodiment 2：
The preparation of nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
0.326 g (1.0 mmol) 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols Schiff is added in 100mL three-necked flasks
Alkali and 12mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 22mL 50 nickel acetate is instilled after heating for dissolving, is being stirred back
8 h of reaction are flowed down, 18mL pyridines are then added dropwise, continue 5 h that flow back, are cooled down, filtering, control solvent volatilization crystallization, it is saturating to obtain brown
Bright crystal, the nickel complex as containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Yield：89.1%.It is molten
Point：86~88 DEG C (dec).
Elementary analysis (C28H22BrClN4O2Ni)：Calculated value：C 54.19, H 3.57, N 9.03；Measured value：C 54.24,
H 3.52, N 9.06.
FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479, 1442, 1375, 1219,
1070。
Crystallographic data：Anorthic system, space group P-1, a=0.89747 (19) nm, b=0.89922 (19) nm, c
=1.7140 (4) nm, α=104.069 (3) °, β=96.547 (2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5)
nm3。
Embodiment 3：
The preparation of nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
0.326 g (1.0 mmol) 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols Schiff is added in 100mL three-necked flasks
Alkali and 20mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 24mL 50 nickel acetate is instilled after heating for dissolving, is being stirred back
9 h of reaction are flowed down, 28mL pyridines are then added dropwise, continue 13 h that flow back, are cooled down, filtering, control solvent volatilization crystallization, it is saturating to obtain brown
Bright crystal, the nickel complex as containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Yield：89.6%.It is molten
Point：86~88 DEG C (dec).
Elementary analysis (C28H22BrClN4O2Ni)：Calculated value：C 54.19, H 3.57, N 9.03；Measured value：C 54.24,
H 3.52, N 9.06.
FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479, 1442, 1375, 1219,
1070。
Crystallographic data：Anorthic system, space group P-1, a=0.89747 (19) nm, b=0.89922 (19) nm, c
=1.7140 (4) nm, α=104.069 (3) °, β=96.547 (2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5)
nm3。
Embodiment 4：
The preparation of nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
1.630 g (5.0 mmol) 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols Schiff is added in 500mL three-necked flasks
Alkali 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, is being stirred
Backflow 7 h of lower reaction, are then added dropwise 90mL pyridines, continue 9 h that flow back, cool down, filtering, control solvent volatilization crystallization, obtain brown
Transparent crystal, the nickel complex as containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Yield：84.6%.
Fusing point：86~88 DEG C (dec).
Elementary analysis (C28H22BrClN4O2Ni)：Calculated value：C 54.19, H 3.57, N 9.03；Measured value：C 54.24,
H 3.52, N 9.06.
FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479, 1442, 1375, 1219,
1070。
Crystallographic data：Anorthic system, space group P-1, a=0.89747 (19) nm, b=0.89922 (19) nm, c
=1.7140 (4) nm, α=104.069 (3) °, β=96.547 (2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5)
nm3。
Embodiment 5：
The preparation of nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
Middle addition 3.260 g (10.0 mmol) 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols in 1000mL three-necked flasks
Schiff and 240mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 210mL 50 nickel acetate is instilled after heating for dissolving,
10 h of lower reaction are being stirred at reflux, 220mL pyridines are then added dropwise, are continuing 15 h that flow back, are being cooled down, filtering, control solvent volatilization knot
Crystalline substance, obtain amber transparent crystal, the nickel complex as containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Production
Rate：83.2%.Fusing point：86~88 DEG C (dec).
Elementary analysis (C28H22BrClN4O2Ni)：Calculated value：C 54.19, H 3.57, N 9.03；Measured value：C 54.24,
H 3.52, N 9.06.
FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479, 1442, 1375, 1219,
1070。
Crystallographic data：Anorthic system, space group P-1, a=0.89747 (19) nm, b=0.89922 (19) nm, c
=1.7140 (4) nm, α=104.069 (3) °, β=96.547 (2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5)
nm3。
Embodiment 6：
The preparation of nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine：
Middle addition 3.260 g (10.0 mmol) 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols in 1000mL three-necked flasks
Schiff and 160mL solvent absolute ethyl alcohols, the ethanol solution of the mmol/L of 225mL 50 nickel acetate is instilled after heating for dissolving,
11 h of lower reaction are being stirred at reflux, 240mL pyridines are then added dropwise, are continuing 11 h that flow back, are being cooled down, filtering, control solvent volatilization knot
Crystalline substance, obtain amber transparent crystal, the nickel complex as containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine.Production
Rate：83.5%.Fusing point：86~88 DEG C (dec).
Elementary analysis (C28H22BrClN4O2Ni)：Calculated value：C 54.19, H 3.57, N 9.03；Measured value：C 54.24,
H 3.52, N 9.06.
FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479, 1442, 1375, 1219,
1070。
Crystallographic data：Anorthic system, space group P-1, a=0.89747 (19) nm, b=0.89922 (19) nm, c
=1.7140 (4) nm, α=104.069 (3) °, β=96.547 (2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5)
nm3。
Test example：
The nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine of the present invention, it is external anti-
Cancer determination of activity 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 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyrrole
The nickel complex of pyridine is 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）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）, human breast cancer cell
（MCF7）, human cervical carcinoma cell（Hela）And human lung carcinoma cell（NCI-H460）Cell line is analyzed, and determines its IC50Value,
As a result as shown in table 1, conclusion is：From data in table, 5- bromosalicylaldehyde 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）, human cervical carcinoma cell（Hela）And human lung carcinoma cell（NCI-H460）With certain
Drug effect, can be as the candidate compound of cancer therapy drug.
Nickel complex cancer therapy drug of the table 1 containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine is external
Active testing data
Nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine prepared by remaining embodiment
With mtt assay to human colon cancer cell（Colo205）, human liver cancer cell（HepG2）, human breast cancer cell（MCF7）, human cervical cancer 1
Cancer cell（Hela）And human lung carcinoma cell（NCI-H460）The same test example of active anticancer method of testing, test result and the base of table 1
This is identical.
Claims (3)
1. a kind of nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine, it is following structural formula
(I) complex：
(I)；Described complex (I) is crystal structure, and its crystallographic data is as follows：Anorthic system, space group P-1, a=
0.89747 (19) nm, b=0.89922 (19) nm, c=1.7140 (4) nm, α=104.069 (3) °, β=96.547
(2) °, γ=100.176 (2) °, Z=2, V=1.3026 (5) nm3；Nickle atom is the distorted octahedron structure of hexa-coordinate in molecule
Type；The infrared data of described complex (I)：FT-IR (KBr, cm-1): 3066, 3053, 1608, 1583, 1479,
1442, 1375, 1219, 1070；The preparation method of described complex (I), it is characterized in that adding 5- bromines in reaction vessel
Salicylidene 4- chlorine o-aminophenol Schiffs and solvent absolute ethyl alcohol, 50 mmol/L nickel acetate is instilled after heating for dissolving
Ethanol solution, 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, filtered, control
Solvent volatilization crystallization, obtains amber transparent crystal, as containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine
Nickel complex；Wherein, the amount ratio of the material of 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and nickel acetate is 1:1~1:
1.2；The dosage of solvent absolute ethyl alcohol is that every mM of 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenol Schiff adds 12~24 milliliters；
The dosage of pyridine is every mM of 14~28 milliliters of 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols Schiff；The dosage of pyridine is every
MM 14~28 milliliters of 5- bromosalicylaldehyde contracting 4- chlorine o-aminophenols Schiff；Described complex (I) has certain heat
Stability range, it can be stabilized below 86 DEG C.
2. prepared by the nickel complex containing 5- bromosalicylaldehydes contracting 4- chlorine o-aminophenol Schiffs and pyridine described in claim 1
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, human lung 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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2015
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Non-Patent Citations (2)
| Title |
|---|
| COMPLEXES OF SOME FIRST SERIES TRANSITION METALS FORMALLY TRICOORDINATED;F .Maggio等，;《INORG. NUCL. CHEM. LETTERS》;19741231;第10卷;第1005-1008页，特别是第1005页第2段第4行至倒数第2行，第1007页结构式、第6-8行、倒数第1行 * |
| 金属配合物抗癌活性的研究进展;刘晶莹等，;《化学试剂》;20031231;第25卷(第5期);第274-276、295页，特别是第275页第2.1节、第275页右栏第3段 * |
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