CN106279253B - Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of one kind and the preparation method and application thereof - Google Patents

Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of one kind and the preparation method and application thereof Download PDF

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CN106279253B
CN106279253B CN201610667636.0A CN201610667636A CN106279253B CN 106279253 B CN106279253 B CN 106279253B CN 201610667636 A CN201610667636 A CN 201610667636A CN 106279253 B CN106279253 B CN 106279253B
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methyl
bis
phenyl
tin
propyl
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CN106279253A (en
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朱小明
邝代治
张复兴
冯泳兰
庾江喜
蒋伍玖
谭宇星
杨春林
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衡阳师范学院
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/22Tin compounds
    • C07F7/2224Compounds having one or more tin-oxygen linkages

Abstract

Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of one kind disclosed by the invention and the preparation method and application thereof are the complex of following structure formula (I).The invention also discloses the preparation methods and application in preparation of anti-tumor drugs of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs.

Description

Bis- [three (2- methyl -2- phenyl) propyl tin] the 5- nitroisophthalic acid esters of one kind are matched Close object and the preparation method and application thereof

Technical field

The present invention relates to a kind of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs, and Preparation method and the complex application in preparation of anti-tumor drugs.

Background technique

Organotin is a kind of metallo-organic compound containing Sn-C key, and bioactivity with higher is being sterilized, killed The fields such as worm, anticancer 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 anticancer activity of cyclohexyl, normal-butyl and phenyl tin compound are stronger, second Base takes second place, and methyl is then almost without anticancer activity.The structure of ligand is to the anticancer activity 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 It is high to close object.

[three (2- methyl -2- phenyl propyl) tin] carboxylates bis- disclosed in European patent EP 0177785B1 are than bis- [three (2- Methyl -2- phenyl propyl) tin] oxide have stronger bioactivity.

Document (chemical journal, 1999,57:210-218.) report: bis- (Tricyclohexyltin) dicarboxylic esters to mosquito with Tetranychus telarius has preferable drug effect.

Document (Chemical Journal of Chinese Universities, 1999,20 (11): 1743-1745.) proves: bis- [three (2- methyl -2- benzene Base propyl) tin] carboxylate have acaricidal activity more stronger than tin tricyclohexylhydroxide.

It is the experiment proved that the object with preferable bioactivity based on bis oxide [three (2- methyl -2- phenyl) propyl tin] Matter, the present invention select bis- [three (2- methyl -2- phenyl propyl) tin] oxides, and ligand 5- nitroisophthalic acid, certain Under the conditions of react, synthesis obtained to NCI-H460 (human lung carcinoma cell), MCF7 (people's breast adenocarcinoma cell), HEPG2 (human liver cancer Cell) the stronger complex of inhibitory activity, for exploitation anticancer drug provide new way.

Summary of the invention

In view of the above-mentioned problems of the prior art, there is provided a kind of bis- [three (2- methyl-for the first object of the present invention 2- phenyl) propyl tin] 5- nitroisophthalic acid ester complex.

The second object of the present invention is to provide above-mentioned bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acids The preparation method of ester complex.

Third mesh of the invention is to provide above-mentioned bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid esters Application of the complex in medicine.

Bis- [three (2- methyl -2- phenyl) propyl tin] the 5- nitroisophthalic acid esters of one kind as first aspect present invention Complex is the complex of following structure formula (I):

(I)。

Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of the invention are through element point Analysis, infrared spectrum analysis and nuclear magnetic resoance spectrum structural analysis, as a result as follows:

Elemental analysis (C68H81NO6Sn2): theoretical value: C, 65.56;H, 6.55;N, 1.12.Measured value: C, 65.59;H, 6.51;N, 1.18.

IR(KBr, v/cm-1): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 vas (COO-), 1304 vs(COO-), 621 v(Sn-C), 557 v(Sn-O)。

1H NMR(CDCl3, 500 MHz),δ(ppm): 8.90,8.88 (s, 3H, Ar-H), 7.30-7.10 (m, 30H, Ar-H), 1.29 (s, 12H, CH2Sn), 1.25 (s, 36H, CH3)。

13C NMR(CDCl3, 125 MHz), δ (ppm): 32.99 (SnCH2), 37.74,37.82 (- CH3), 37.90 (Ar-C), 125.38,126.10,127.67,128.56,135.29,136.64,148.17,150.75 (Ar), 167.96(COO)。

119Sn NMR(CDCl3,186 MHz), δ(ppm): 108.16。

The design feature of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of the invention It is: tin core there are two containing in molecule, and each tin atom is four-coordination distortion tetrahedral configuration.

Bis- [three (2- methyl -2- phenyl) propyl tin] the 5- nitroisophthalic acid esters of one kind as second aspect of the present invention Preparation method, sequentially add 5- nitroisophthalic acid, bis- [three (2- methyl -2- phenyl third in order in the reaction vessel Base) tin] oxide and solvent methanol, the reaction 8~for 24 hours under conditions of temperature is 50 ~ 65 DEG C;It is cooling, filtering, at 20 ~ 35 DEG C Under conditions of, control solvent volatilization crystallization obtains white solid, between as bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitros Phthalic acid ester complex.

In a preferred embodiment of the invention, the 5- nitroisophthalic acid, bis- [three (2- methyl -2- phenyl third Base) tin] the mass ratio of the material of both oxides is 1:(1 ~ 1.05).

In a preferred embodiment of the invention, the solvent methanol dosage is every mM of bis- [three (2- methyl -2- Phenyl propyl) tin] oxide adds 30 ~ 45 milliliters.

Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid esters as third aspect present invention cooperate The structure application in preparation of anti-tumor drugs of object.

Applicant has carried out anti tumor activity in vitro confirmation research to above-mentioned complex, confirms that the complex has centainly Anti-tumor biological, that is to say, that the purposes of above-mentioned complex is application in preparation of anti-tumor drugs, specifically It is to prepare anti-human lung-cancer medicament, human breast carcinoma, the application in human liver cancer drug.

Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of the invention, to human lung cancer Drug, human breast carcinoma, human liver cancer drug etc. show good anticancer activity, can prepare anti-lung cancer, anti-mammary gland using it as raw material Cancer, medicines resistant to liver cancer.Compared with the platinum-containing anticancer drug being commonly used, bis- [three (2- methyl -2- phenyl) third of the invention Ji Xi] 5- nitroisophthalic acid ester complex has the characteristics that anticancer activity is high, at low cost, preparation method is simple, for exploitation Anticancer drug provides new way.

Detailed description of the invention

Fig. 1 is the IR spectrogram of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs.

Fig. 2 is bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs1H NMR spectra.

Fig. 3 is bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs13C NMR spectra.

Fig. 4 is bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs119Sn H NMR spectroscopy Figure.

Fig. 5 is the TG-DTG curve of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs.

Specific embodiment

By following embodiment, present invention be described in more detail, 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 bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs:

Sequentially add 5- nitroisophthalic acid 0.2111g (1mmol), bis- [three in order in 100ml round-bottomed flask (2- methyl -2- phenyl propyl) tin] oxide 1.0532g (1mmol), solvent methanol 30mL, the condition for being 50 ~ 65 DEG C in temperature Lower reaction 8h;Cooling, filtering, under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization obtains white solid, as bis- [three (2- Methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complex.Yield: 74%, fusing point: 139-140 DEG C.

Elemental analysis (C68H81NO6Sn2): theoretical value: C, 65.56;H, 6.55;N, 1.12.Measured value: C, 65.59;H, 6.51;N, 1.18.

IR(KBr, v/cm-1): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 vas (COO-), 1304 vs(COO-), 621 v(Sn-C), 557 v(Sn-O)。

1H NMR(CDCl3, 500 MHz),δ(ppm): 8.90,8.88 (s, 3H, Ar-H), 7.30-7.10 (m, 30H, Ar-H), 1.29 (s, 12H, CH2Sn), 1.25 (s, 36H, CH3)。

13C NMR(CDCl3, 125 MHz), δ (ppm): 32.99 (SnCH2), 37.74,37.82 (- CH3), 37.90 (Ar-C), 125.38,126.10,127.67,128.56,135.29,136.64,148.17,150.75 (Ar), 167.96(COO)。

119Sn NMR(CDCl3,186 MHz), δ(ppm): 108.16。

Embodiment 2:

The preparation of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs:

Sequentially add 5- nitroisophthalic acid 0.2116g (1mmol), bis- [three in order in 100ml round-bottomed flask (2- methyl -2- phenyl propyl) tin] oxide 1.1060g (1.05mmol), solvent methanol 47mL are 50 ~ 65 DEG C in temperature Under the conditions of react 12h;Cooling, filtering, under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization obtains white solid, as double [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complex.Yield: 76%, fusing point: 139-140 DEG C.

Elemental analysis (C68H81NO6Sn2): theoretical value: C, 65.56;H, 6.55;N, 1.12.Measured value: C, 65.59;H, 6.51;N, 1.18.

IR(KBr, v/cm-1): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 vas (COO-), 1304 vs(COO-), 621 v(Sn-C), 557 v(Sn-O)。

1H NMR(CDCl3, 500 MHz),δ(ppm): 8.90,8.88 (s, 3H, Ar-H), 7.30-7.10 (m, 30H, Ar-H), 1.29 (s, 12H, CH2Sn), 1.25 (s, 36H, CH3)。

13C NMR(CDCl3, 125 MHz), δ (ppm): 32.99 (SnCH2), 37.74,37.82 (- CH3), 37.90 (Ar-C), 125.38,126.10,127.67,128.56,135.29,136.64,148.17,150.75 (Ar), 167.96(COO)。

119Sn NMR(CDCl3,186 MHz), δ(ppm): 108.16。

Embodiment 3:

The preparation of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs:

Sequentially add 5- nitroisophthalic acid 0.4218g (2mmol), bis- [three in order in 100ml round-bottomed flask (2- methyl -2- phenyl propyl) tin] oxide 2.2112g (2.1mmol), solvent methanol 63mL, the item for being 50 ~ 65 DEG C in temperature 18h is reacted under part;Cooling, filtering, under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization obtains white solid, and as bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complex.Yield: 72%, fusing point: 139-140 DEG C.

Elemental analysis (C68H81NO6Sn2): theoretical value: C, 65.56;H, 6.55;N, 1.12.Measured value: C, 65.59;H, 6.51;N, 1.18.

IR(KBr, v/cm-1): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 vas (COO-), 1304 vs(COO-), 621 v(Sn-C), 557 v(Sn-O)。

1H NMR(CDCl3, 500 MHz),δ(ppm): 8.90,8.88 (s, 3H, Ar-H), 7.30-7.10 (m, 30H, Ar-H), 1.29 (s, 12H, CH2Sn), 1.25 (s, 36H, CH3)。

13C NMR(CDCl3, 125 MHz), δ (ppm): 32.99 (SnCH2), 37.74,37.82 (- CH3), 37.90 (Ar-C), 125.38,126.10,127.67,128.56,135.29,136.64,148.17,150.75 (Ar), 167.96(COO)。

119Sn NMR(CDCl3,186 MHz), δ(ppm): 108.16。

Embodiment 4:

The preparation of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs:

Sequentially add 5- nitroisophthalic acid 0.4221g (2mmol), bis- [three in order in 100ml round-bottomed flask (2- methyl -2- phenyl propyl) tin] oxide 2.1056 (2mmol), solvent methanol 70mL, the condition for being 50 ~ 65 DEG C in temperature Lower reaction is for 24 hours;Cooling, filtering, under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization obtains white solid, and as bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complex.Yield: 73%, fusing point: 139-140 DEG C.

Elemental analysis (C68H81NO6Sn2): theoretical value: C, 65.56;H, 6.55;N, 1.12.Measured value: C, 65.59;H, 6.51;N, 1.18.

IR(KBr, v/cm-1): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 vas (COO-), 1304 vs(COO-), 621 v(Sn-C), 557 v(Sn-O)。

1H NMR(CDCl3, 500 MHz), δ (ppm): 8.90,8.88 (s, 3H, Ar-H), 7.30-7.10 (m, 30H, Ar-H), 1.29 (s, 12H, CH2Sn), 1.25 (s, 36H, CH3)。

13C NMR(CDCl3, 125 MHz), δ (ppm): 32.99 (SnCH2), 37.74,37.82 (- CH3), 37.90 (Ar-C), 125.38,126.10,127.67,128.56,135.29,136.64,148.17,150.75 (Ar), 167.96(COO)。

119Sn NMR(CDCl3,186 MHz), δ(ppm): 108.16。

Embodiment 5:

The preparation of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs:

Sequentially add 5- nitroisophthalic acid 0.4223 (2mmol), bis- [three (2- in order in 100ml round-bottomed flask Methyl -2- phenyl propyl) tin] oxide 2.1581g (2.05mmol), solvent methanol 70mL, the condition for being 50 ~ 65 DEG C in temperature Lower reaction is for 24 hours;Cooling, filtering, under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization obtains white solid, and as bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complex.Yield: 72%, fusing point: 139-140 DEG C.

Elemental analysis (C68H81NO6Sn2): theoretical value: C, 65.56;H, 6.55;N, 1.12.Measured value: C, 65.59;H, 6.51;N, 1.18.

IR(KBr, v/cm-1): 3086, 3057, 3021, 2959, 2922, 2860 v(C-H), 1670 vas (COO-), 1304 vs(COO-), 621 v (Sn-C), 557 v (Sn-O)。

1H NMR(CDCl3, 500 MHz), δ (ppm): 8.90,8.88 (s, 3H, Ar-H), 7.30-7.10 (m, 30H, Ar-H), 1.29 (s, 12H, CH2Sn), 1.25 (s, 36H, CH3)。

13C NMR(CDCl3, 125 MHz), δ (ppm): 32.99 (SnCH2), 37.74,37.82 (- CH3), 37.90 (Ar-C), 125.38,126.10,127.67,128.56,135.29,136.64,148.17,150.75 (Ar), 167.96(COO)。

119Sn NMR(CDCl3,186 MHz), δ(ppm): 108.16。

Test example: bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of the invention, Anticancer Activity in vitro measurement is realized by MTT experimental method.

MTT analyses method: restoring 3- (4,5-Dimethylthiazol-2-yl) -2,5- with metabolism Based on diArenyltetrazolium bromide.Succinate dehydrogenase in living cells mitochondria can make exogenous MTT It is reduced to bluish violet crystallization first a ceremonial jade-ladle, used in libation (Formazan) of water-insoluble and is deposited in cell, and dead cell is without this function.Diformazan Base sulfoxide (DMSO) can dissolve the first a ceremonial jade-ladle, used in libation in cell, with the optical density of microplate reader measurement characteristic wavelength, can reflect living cells indirectly Quantity.

Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs pair are measured using mtt assay The inhibitory activity of human lung carcinoma cell (NCI-H460), human breast cancer cell (MCF7), human liver cancer cell (HepG2).

Cell strain and cultivating system: NCI-H460, MCF7 and HepG2 cell strain are derived from American tissue incubator (ATCC). With contain 10% fetal calf serum RPMI1640 (GIBICO company) culture medium, in 5% (volume fraction) CO2, 37 DEG C of saturated humidity trainings It supports and carries out in vitro culture in case.

Test process: test medical fluid (0.1nM-10uM) is added separately in each hole according to the concentration gradient of concentration, Each concentration sets 6 parallel holes.Experiment is divided into drug test group (the test medicine for being separately added into various concentration), control group (only adds Test medicine is not added in culture solution and cell) and blank group (only adding culture solution, cell and test medicine is not added).By the orifice plate after dosing 37 DEG C are placed in, 5%CO272h is cultivated in incubator.The activity of control drug is measured according to the method for test sample.It is cultivating In orifice plate after 72h, every hole adds MTT40uL (being made into 4mg/mL with D-Hanks buffer).After 37 DEG C of placement 4h, remove Clear liquid.Every hole adds 150uL DMSO, vibrates 5min, makes Formazan crystallization dissolution.Finally, using automatic microplate reader in 570nm The optical density in each hole is detected at wavelength.

Data processing: data processing uses GraAr Pad Prism version5.0 program, compound IC50Pass through program In be fitted to obtain with the nonlinear regression model (NLRM) of S-shaped dose response.

With MTT analytic approach to human lung carcinoma cell (NCI-H460) cell strain, human breast cancer cell (MCF7) cell strain, people liver Cancer cell (HepG2) cell strain is analyzed, its IC is measured50Value, the results are shown in Table 1, conclusion are as follows: from the data in the table, Anticancer drug of the invention, it is higher to human lung cancer, human breast carcinoma, human liver cancer anticancer activity, it can be used as the candidates of anticancer drug Close object.

Bis- [three (2- methyl -2- phenyl) propyl tin] the 5- nitroisophthalic acid ester complex anticancer drugs of table 1 are lived in vitro Property test data

Human lung carcinoma cell Human breast cancer cell Human liver cancer cell Cell strain NCI-H460 MC-7 HEPG2 IC50 μM 5.29 5.75 7.52

Remaining embodiment preparation bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs with Mtt assay surveys the anticancer activity of human lung carcinoma cell (NCI-H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7) The same test example of method for testing, test result and table 1 are essentially identical.

Claims (4)

1. a kind of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs are following structural formula (I) complex:
Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs have certain thermostabilization model It encloses, can be stabilized at 300 DEG C or less, bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid esters, Its infrared data: IR (KBr, cm-1):3086,3057,3021,2959,2922,2860v(C-H),1670vas(COO-), 1304vs(COO-),621v(Sn-C),557v(Sn-O);Its nuclear-magnetism modal data:1H NMR(CDCl3, 500MHz), δ (ppm): 8.90,8.88 (s, 3H, Ar-H), 7.30-7.10 (m, 30H, Ar-H), 1.29 (s, 12H, CH2Sn), 1.25 (s, 36H, CH3) ;13C NMR(CDCl3, 125MHz), δ (ppm): 32.99 (SnCH2), 37.74,37.82 (- CH3), 37.90 (Ar-C), 125.38,126.10,127.67,128.56,135.29,136.64,148.17,150.75 (Ar), 167.96 (COO);119Sn NMR(CDCl3,186MHz),δ(ppm):108.16;Wherein, bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitros Containing there are two tin core in M-phthalic acid ester molecule, and two tin atoms are four-coordination distortion tetrahedral configuration, and described bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complex fusing point be 139-140 DEG C.
2. the system of bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs described in claim 1 Preparation Method, which is characterized in that sequentially add 5- nitroisophthalic acid, bis- [three (2- methyl -2- in order in the reaction vessel Phenyl propyl) tin] oxide and solvent methanol, the reaction 8~for 24 hours under conditions of temperature is 50~65 DEG C;It is cooling, filtering, Under conditions of 20~35 DEG C, control solvent volatilization crystallization obtains white solid, as bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester, both the 5- nitroisophthalic acid, bis- [three (2- methyl -2- phenyl propyl) tin] oxides The mass ratio of the material be 1:(1~1.05), the solvent anhydrous methanol dosage be every mM of bis oxide [three (2- methyl -2- benzene Base) propyl tin] plus 30~45 milliliters.
3. bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs described in claim 1 are being made Application in standby anticancer drug.
4. application as claimed in claim 3, wherein the cancer is lung cancer, breast cancer or liver cancer.
CN201610667636.0A 2016-08-15 2016-08-15 Bis- [three (2- methyl -2- phenyl) propyl tin] 5- nitroisophthalic acid ester complexs of one kind and the preparation method and application thereof CN106279253B (en)

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