CN107011375A - A kind of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] and preparation method and application - Google Patents
A kind of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] and preparation method and application Download PDFInfo
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- CN107011375A CN107011375A CN201710198105.6A CN201710198105A CN107011375A CN 107011375 A CN107011375 A CN 107011375A CN 201710198105 A CN201710198105 A CN 201710198105A CN 107011375 A CN107011375 A CN 107011375A
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- tin
- butyl ester
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- acid butyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/22—Tin compounds
- C07F7/226—Compounds with one or more Sn-S linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Abstract
A kind of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] disclosed by the invention and preparation method and application, is the complex of following structure formula (I).The invention also discloses the preparation method of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] and the application in antineoplastic is prepared.
Description
Technical field
The present invention relates to a kind of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs], and its preparation side
Method, and application of this pair [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complex] in antineoplastic is prepared.
Background technology
Organotin is the metallo-organic compound that a class contains Sn-C keys, with higher bioactivity, is sterilizing, is killing
The fields such as worm, cancer therapy drug preparation have a wide range of applications.Existing research shows that the alkyl R in organotin is to determine
The principal element of compound anti-cancering activity height, e.g., the active anticancer of cyclohexyl, normal-butyl and phenyl tin compound are stronger, second
Base takes second place, and methyl is then almost without active anticancer.The structure of part is to the active anticancer of complex and the wide spectrum of killing cancer cell
Property also plays an important role, it is demonstrated experimentally that the bioactivity of organotin carboxylate complex is often than corresponding organotin
Compound is high.
Chinese patent CN 103396437B disclose Tricyclohexyltin carboxylate and are preparing treatment cervical carcinoma, breast cancer, liver
Applied in the medicine of cancer, colon cancer and lung cancer.
Chinese patent CN 103087325B disclose being controlled in preparation for the carboxylate polymer of Tricyclohexyltin containing ferrocenyl
Applied in the medicine for treating liver cancer, nasopharyngeal carcinoma, breast cancer, colon cancer and lung cancer.
It is that the experiment proved that the material with preferable bioactivity based on organotin carboxylate, the present invention two (adjacent chlorine of selection
Benzyl) stannous chloride, with part butyl salicylate, reacts, synthesis has obtained to NCI-H460 that (human lung cancer is thin under certain condition
Born of the same parents), A549 (human lung carcinoma cell), the stronger compound of MCF7 (people's breast adenocarcinoma cell) inhibitory activity, for exploitation anticarcinogen
Thing provides new way.
The content of the invention
In view of the above-mentioned problems of the prior art, the first object of the present invention there is provided a kind of double [(adjacent chlorine of chlorination two
Benzyl) tin thiosalicylic acid butyl ester complex].
The second object of the present invention is to provide above-mentioned double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs]
Preparation method.
The 3rd mesh of the present invention is to provide above-mentioned double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] and existed
Prepare the application in cancer therapy drug.
It is double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complex] as one kind of first aspect present invention, its
For the complex of following structure formula (I)：
The molecule of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] forms abnormal centered on tin atom
Become trigonal biyramid configuration, its crystal structure unit is different chlorination two (o-chlorobenzyl) the tin thiosalicylic acid fourth of 2 bond parameters
The condensate of ester complex molecule.
Double [chlorination two (o-chlorobenzyl) the tin thiosalicylic acid butyl ester complexs] of the present invention is through elementary analysis, infrared spectrum
Analysis analysis, it is as a result as follows：
Elementary analysis (C25H25Cl3O4SSn4)：Theoretical value：C, 48.86；H, 4.10.Measured value：C, 48.87；H, 4.13.
IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-),648v
(Sn-C),434v(Sn-O)。
Double [chlorination two (o-chlorobenzyl) the tin thiosalicylic acid butyl ester complexs] of the present invention is crystal structure, its crystallography
Data：Crystal belongs to anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm, c=1.37136 (9) nm,
α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=1.31610 (14) nm3, Dc
=1.551Mgm-3, μ (MoKa)=1.374mm-1, F (000)=616,2.42 ° of 27.55 ° of ＜ θ ＜, crystalline size：
0.23x0.21x0.20mm, R=0.0494, wR=0.1424.
It is used as one kind double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complex] of second aspect of the present invention
Preparation method, sequentially adds thiosalicylic acid butyl ester, two (o-chlorobenzyl) stannous chloride, three second in order in microwave reaction tank
Amine and etoh solvent.It is placed in microwave reactor, 1~3h is reacted under conditions of temperature is 100 DEG C；Cooling, filtering,
Solvent volatilization crystallization is controlled under conditions of 20~35 DEG C, colourless transparent crystal is obtained, as double [chlorination two (o-chlorobenzyl) tin is thio
Butyl salicylate complex].
In a preferred embodiment of the invention, the thiosalicylic acid butyl ester, two (o-chlorobenzyl) stannous chloride, three
The mol ratio of ethamine is 1:(1-1.1):1.
In a preferred embodiment of the invention, the etoh solvent consumption is every mM two (o-chlorobenzyl) dichloro
Change tin add 10~20 milliliters.
Exist as one kind double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] of third aspect present invention
Prepare the application in cancer therapy drug.
Applicant has carried out anti tumor activity in vitro to above-mentioned complex and has confirmed research, confirms that the complex has necessarily
Anti-tumor biological, that is to say, that the purposes of above-mentioned complex is the application in antineoplastic is prepared, specifically
It is the application in anti-human lung-cancer medicament, human breast carcinoma medicine is prepared.
Double [chlorination two (o-chlorobenzyl) the tin thiosalicylic acid butyl ester complexs] of the present invention has certain thermally-stabilised model
Enclose, can be stabilized below 175 DEG C.It shows good active anticancer to human lung cancer medicine, human breast carcinoma etc., can be with it
Anti-lung cancer, anti-breast cancer medicines are prepared for raw material.Compared with the platinum-containing anticancer drug generally used at present, double [chlorine of the invention
Change two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] there is the spies such as active anticancer is high, cost is low, preparation method is simple
Point, new way is provided for exploitation cancer therapy drug.
Brief description of the drawings
Fig. 1：For the crystal molecular structure figure of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].
Fig. 2：For the IR spectrograms of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].
Fig. 3：Scheme for the TG of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].
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 limitation of example.
Embodiment 1：
The preparation of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs]：
Sequentially add thiosalicylic acid butyl ester 0.2105g (1mmol), two (adjacent chlorine in order in 30ml microwave reaction tanks
Benzyl) stannous chloride 0.4403g (1mmol), triethylamine 0.1018 (1mmol), etoh solvent 10mL, be placed on microwave reaction
In device, 1h is reacted under conditions of temperature is 100 DEG C；Cooling, filtering controls solvent volatilization knot under conditions of 20~35 DEG C
Crystalline substance, obtains colourless transparent crystal, is double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].Yield：80%, melt
Point：80-81℃.
Elementary analysis (C25H25Cl3O4SSn4)：Theoretical value：C, 48.86；H, 4.10.Measured value：C, 48.87；H, 4.13.
IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-),648v
(Sn-C),434v(Sn-O)。
Its crystallographic data：Crystal belongs to anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm,
C=1.37136 (9) nm, α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=
1.31610(14)nm3, Dc=1.551Mgm-3, μ (MoKa)=1.374mm-1, F (000)=616,2.42 ° of ＜ θ ＜
27.55 °, crystalline size：0.23x0.21x0.20mm, R=0.0494, wR=0.1424.
Embodiment 2：
The preparation of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs]：
Sequentially add thiosalicylic acid butyl ester 0.2105g (1mmol), two (adjacent chlorine in order in 30ml microwave reaction tanks
Benzyl) stannous chloride 0.4403g (1mmol), triethylamine 0.1018 (1mmol), etoh solvent 10mL, be placed on microwave reaction
In device, 2h is reacted under conditions of temperature is 100 DEG C；Cooling, filtering controls solvent volatilization knot under conditions of 20~35 DEG C
Crystalline substance, obtains colourless transparent crystal, is double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].Yield：82%, melt
Point：80-81℃.
Elementary analysis (C25H25Cl3O4SSn4)：Theoretical value：C, 48.86；H, 4.10.Measured value：C, 48.87；H, 4.13.
IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-),648v
(Sn-C),434v(Sn-O)。
Its crystallographic data：Crystal belongs to anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm,
C=1.37136 (9) nm, α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=
1.31610(14)nm3, Dc=1.551Mgm-3, μ (MoKa)=1.374mm-1, F (000)=616,2.42 ° of ＜ θ ＜
27.55 °, crystalline size：0.23x0.21x0.20mm, R=0.0494, wR=0.1424.
Embodiment 3：
The preparation of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs]：
Sequentially add thiosalicylic acid butyl ester 0.2109g (1mmol), two (adjacent chlorine in order in 30ml microwave reaction tanks
Benzyl) stannous chloride 0.4403g (1mmol), triethylamine 0.1012 (1mmol), etoh solvent 10mL, be placed on microwave reaction
In device, 3h is reacted under conditions of temperature is 100 DEG C；Cooling, filtering controls solvent volatilization knot under conditions of 20~35 DEG C
Crystalline substance, obtains colourless transparent crystal, is double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].Yield：82%, melt
Point：80-81℃.
Elementary analysis (C25H25Cl3O4SSn4)：Theoretical value：C, 48.86；H, 4.10.Measured value：C, 48.87；H, 4.13.
IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-),648v
(Sn-C),434v(Sn-O)。
Its crystallographic data：Crystal belongs to anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm,
C=1.37136 (9) nm, α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=
1.31610(14)nm3, Dc=1.551Mgm-3, μ (MoKa)=1.374mm-1, F (000)=616,2.42 ° of ＜ θ ＜
27.55 °, crystalline size：0.23x0.21x0.20mm, R=0.0494, wR=0.1424.
Embodiment 4：
The preparation of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs]：
Sequentially add thiosalicylic acid butyl ester 0.2107g (1mmol), two (adjacent chlorine in order in 30ml microwave reaction tanks
Benzyl) stannous chloride 0.4402g (1mmol), triethylamine 0.1014 (1mmol), etoh solvent 20mL, be placed on microwave reaction
In device, 2h is reacted under conditions of temperature is 100 DEG C；Cooling, filtering controls solvent volatilization knot under conditions of 20~35 DEG C
Crystalline substance, obtains colourless transparent crystal, is double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].Yield：82%, melt
Point：80-81℃.
Elementary analysis (C25H25Cl3O4SSn4)：Theoretical value：C, 48.86；H, 4.10.Measured value：C, 48.87；H, 4.13.
IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-),648v
(Sn-C),434v(Sn-O)。
Its crystallographic data：Crystal belongs to anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm,
C=1.37136 (9) nm, α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=
1.31610(14)nm3, Dc=1.551Mgm-3, μ (MoKa)=1.374mm-1, F (000)=616,2.42 ° of ＜ θ ＜
27.55 °, crystalline size：0.23x0.21x0.20mm, R=0.0494, wR=0.1424.
Embodiment 5：
The preparation of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs]：
Sequentially add thiosalicylic acid butyl ester 0.2107g (1mmol), two (adjacent chlorine in order in 30ml microwave reaction tanks
Benzyl) stannous chloride 0.4852g (1.1mmol), triethylamine 0.1014 (1mmol), etoh solvent 10mL, be placed on microwave anti-
Answer in device, 2h is reacted under conditions of temperature is 100 DEG C；Cooling, filtering controls solvent volatilization knot under conditions of 20~35 DEG C
Crystalline substance, obtains colourless transparent crystal, is double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].Yield：81%, melt
Point：80-81℃.
Elementary analysis (C25H25Cl3O4SSn4)：Theoretical value：C, 48.86；H, 4.10.Measured value：C, 48.87；H, 4.13.
IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-),648v
(Sn-C),434v(Sn-O)。
Its crystallographic data：Crystal belongs to anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm,
C=1.37136 (9) nm, α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=
1.31610(14)nm3, Dc=1.551Mgm-3, μ (MoKa)=1.374mm-1, F (000)=616,2.42 ° of ＜ θ ＜
27.55 °, crystalline size：0.23x0.21x0.20mm, R=0.0494, wR=0.1424.
Embodiment 6：
The preparation of double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs]：
Sequentially add thiosalicylic acid butyl ester 0.4207g (2mmol), two (adjacent chlorine in order in 30ml microwave reaction tanks
Benzyl) stannous chloride 0.8816g (2mmol), triethylamine 0.2025 (2mmol), etoh solvent 20mL, be placed on microwave reaction
In device, 2h is reacted under conditions of temperature is 100 DEG C；Cooling, filtering controls solvent volatilization knot under conditions of 20~35 DEG C
Crystalline substance, obtains colourless transparent crystal, is double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs].Yield：79%, melt
Point：80-81℃.
Elementary analysis (C25H25Cl3O4SSn4)：Theoretical value：C, 48.86；H, 4.10.Measured value：C, 48.87；H, 4.13.
IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-),648v
(Sn-C),434v(Sn-O)。
Its crystallographic data：Crystal belongs to anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm,
C=1.37136 (9) nm, α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=
1.31610(14)nm3, Dc=1.551Mgm-3, μ (MoKa)=1.374mm-1, F (000)=616,2.42 ° of ＜ θ ＜
27.55 °, crystalline size：0.23x0.21x0.20mm, R=0.0494, wR=0.1424.
Test example：
Double [chlorination two (o-chlorobenzyl) the tin thiosalicylic acid butyl ester complexs] of the present invention, its Anticancer Activity in vitro is determined
Realized by MTT experiment method.
MTT analyses method：
To be metabolized reduction 3- (4,5-Dimethylthiazol-2-yl) -2,5-diArenyltetrazolium
Based on bromide.Succinate dehydrogenase in living cells mitochondria can make exogenous MTT be reduced to the bluish violet of water-insoluble
Crystallization first a ceremonial jade-ladle, used in libation (Formazan) is simultaneously deposited in cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO) (DMSO) can dissolve cell
In first a ceremonial jade-ladle, used in libation, with ELIASA determine characteristic wavelength optical density, living cells quantity can be reflected indirectly.
Double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester cooperations of the preparation of embodiment 1 are determined using mtt assay
Thing] to human lung carcinoma cell (NCI-H460), human lung carcinoma cell (A549), human breast cancer cell (MCF7) inhibitory activity.
Cell line and cultivating system：NCI-H460, A549 and MCF7 cell line are derived from American. tissue incubator (ATCC).With
RPMI1640 (GIBICO companies) culture medium containing 10% hyclone, in 5% (volume fraction) CO2, 37 DEG C of saturated humidity trainings
Support and in vitro culture is carried out in case.
Test process：Test decoction (0.0032uM-10uM) is added separately to each hole according to the concentration gradient of concentration
In, each concentration sets 3 parallel holes.Experiment is divided into drug test group (the test medicine for being separately added into various concentrations), control group (only
Plus nutrient solution and cell, it is not added with testing medicine) and blank group (only adding nutrient solution, be not added with cell and test medicine).By the hole after dosing
Plate is placed in 37 DEG C, 5%CO272h is cultivated in incubator.The activity of control drug is determined according to the method for test sample.In culture
In orifice plate after 72h, add MTT40uL (being made into 4mg/mL with D-Hanks buffer solutions) per hole.After 37 DEG C are placed 4h, remove
Supernatant.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 GraAr Pad Prism version5.0 programs, compound IC50Pass through program
In there is S-shaped dose response nonlinear regression model (NLRM) be fitted and obtain.
With MTT analytic approach to human lung carcinoma cell (NCI-H460) cell line, human lung carcinoma cell (A549) cell line, people's mammary gland
Cancer cell (MCF7) cell line is analyzed, and determines its IC50Value, as a result as shown in table 1, conclusion is：The data in table, this
Double [chlorination two (o-chlorobenzyl) the tin thiosalicylic acid butyl ester complexs] of invention is as cancer therapy drug, to human lung cancer, people's mammary gland
Cancer activity it is higher, can as cancer therapy drug candidate compound.
1 pair, table [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complex] cancer therapy drug external activity test number
According to.
| Human lung carcinoma cell | Human lung carcinoma cell | Human breast cancer cell | |
| Cell line | NCI-H460 | A549 | MCF7 |
| IC50μM | 37 | 9.15 | 8.12 |
Double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] prepared by remaining embodiment is with mtt assay to people
The active anticancer method of testing of lung carcinoma cell (NCI-H460), human lung carcinoma cell (A549) and human breast cancer cell (MCF7) is with examination
Example is tested, test result and table 1 are essentially identical.
Claims (8)
- A kind of 1. double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs], it is characterised in that be following structural formula (I) complex：
- 2. it is as claimed in claim 1 double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complex] containing one kind, its Ir data：IR(KBr,cm-1):3057,2957,2930,2870v(C-H),1645vas(COO-),1468vs(COO-), 648v(Sn-C),434v(Sn-O)。
- Double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] 3. as claimed in claim 1, wherein, it is described Double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complexs] are crystal structure, and its crystallographic data is as follows：Crystal belongs to Anorthic system, space group P1, a=1.01874 (6) nm, b=1.06150 (7) nm, c=1.37136 (9) nm, α=106.7700 (10) °, β=93.7330 (10) °, γ=109.5810 (10) °, Z=2, V=1.31610 (14) nm3, molecule using tin atom as Distortion trigonal biyramid configuration is centrally formed, its crystal structure unit is different chlorination two (o-chlorobenzyl) the tin sulphur of 2 bond parameters For the condensate of butyl salicylate complex molecule.
- 4. double [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester cooperations described in any one of claims 1 to 3 claim Thing] preparation method, it is characterised in that sequentially add thiosalicylic acid butyl ester, two (adjacent benzyl chlorides in order in microwave reaction tank Base) stannous chloride, triethylamine and etoh solvent.It is placed in microwave reactor, 1- is reacted under conditions of temperature is 100 DEG C 3h；Cooling, filtering controls solvent volatilization crystallization under conditions of 20~35 DEG C, obtains colourless transparent crystal, is double [chlorinations two (o-chlorobenzyl) tin thiosalicylic acid butyl ester complex].
- 5. preparation method as claimed in claim 4, it is characterised in that the thiosalicylic acid butyl ester, two (o-chlorobenzyls) two Stannic chloride, the mol ratio of triethylamine are 1:(1-1.1):1.
- 6. preparation method as claimed in claim 4, it is characterised in that the etoh solvent consumption is every mM two (adjacent chlorine Benzyl) stannous chloride adds 10~and 20 milliliters.
- 7. double described in any one of claims 1 to 3 claim, [chlorination two (o-chlorobenzyl) tin thiosalicylic acid butyl ester coordinates Thing] prepare treating cancer medicine in application.
- 8. the application described in claim 7, wherein the cancer is lung cancer or breast cancer.
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| CN108864174A (en) * | 2018-04-02 | 2018-11-23 | 衡阳师范学院 | Three (o-chlorobenzyl) tin salicylates of one kind and preparation method and application |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864174A (en) * | 2018-04-02 | 2018-11-23 | 衡阳师范学院 | Three (o-chlorobenzyl) tin salicylates of one kind and preparation method and application |
| CN108864174B (en) * | 2018-04-02 | 2020-12-11 | 衡阳师范学院 | Tris (o-chlorobenzyl) tin salicylate, preparation method and application thereof |
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| CN107011375B (en) | 2019-04-12 |
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