CN106279253A - A kind of double [three (2 methyl 2 phenyl) propyl group stannum] 5 nitroisophthalic acid ester coordination compounds and preparation method and application - Google Patents

A kind of double [three (2 methyl 2 phenyl) propyl group stannum] 5 nitroisophthalic acid ester coordination compounds and preparation method and application Download PDF

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CN106279253A
CN106279253A CN201610667636.0A CN201610667636A CN106279253A CN 106279253 A CN106279253 A CN 106279253A CN 201610667636 A CN201610667636 A CN 201610667636A CN 106279253 A CN106279253 A CN 106279253A
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phenyl
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propyl group
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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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Hengyang Normal University
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Abstract

Double [three (2 methyl 2 phenyl) propyl group stannum] 5 nitroisophthalic acid ester coordination compounds of one disclosed by the invention and preparation method and application, for the coordination compound of following structure formula (I).The invention also discloses the preparation method of double [three (2 methyl 2 phenyl) propyl group stannum] 5 nitroisophthalic acid ester coordination compounds and the application in preparing antitumor drug.

Description

A kind of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester is joined Compound and preparation method and application
Technical field
The present invention relates to a kind of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound, and Its preparation method, and the application that this coordination compound is in preparing antitumor drug.
Background technology
Organotin is the metallo-organic compound that a class contains Sn-C key, has higher biological activity, in sterilization, kills Worm, cancer therapy drug the field such as are prepared and are had a wide range of applications.Existing research shows, 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 phenyltin compound is relatively strong, second Base takes second place, and methyl is then almost without active anticancer.The structure of part is to the active anticancer of coordination compound and the wide spectrum of killing cancerous cell Property also plays an important role, it is demonstrated experimentally that the biological activity of organotin carboxylate coordination compound is often than corresponding organotin Compound is high.
Disclosed in European patent EP 0177785B1, double [three (2-methyl-2-phenyl propyl) stannum] carboxylates are than double [three (2- Methyl-2-phenyl propyl) stannum] oxide has higher biological activity.
Document (chemistry journal, 1999,57:210-218.) report: double (Tricyclohexyltin) dicarboxylic esters to mosquito with Tetranychus telarius has preferable drug effect.
Document (SCI, 1999,20 (11): 1743-1745.) proves: double [three (2-methyl-2-benzene Base propyl group) stannum] carboxylate has the acaricidal activity more higher than tin tricyclohexylhydroxide.
It is to the experiment proved that there is preferable bioactive thing based on bis oxide [three (2-methyl-2-phenyl) propyl group stannum] Matter, the present invention selects double [three (2-methyl-2-phenyl propyl) stannum] oxide, and part 5-nitroisophthalic acid, necessarily Under the conditions of react, synthesis obtained NCI-H460 (human lung carcinoma cell), MCF7 (people's breast adenocarcinoma cell), HEPG2 (people's hepatocarcinoma Cell) the stronger coordination compound of inhibitory activity, provide new way for exploitation cancer therapy drug.
Summary of the invention
The problem existed for above-mentioned prior art, the first object of the present invention there is provided a kind of double [three (2-methyl- 2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.
The second object of the present invention is to provide above-mentioned double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid The preparation method of ester coordination compound.
3rd mesh of the present invention is to provide above-mentioned double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester Coordination compound application in medicine.
A kind of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid esters as first aspect present invention Coordination compound, it is the coordination compound of following structure formula (I):
(I)。
Double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds of the present invention divide through element Analysis, infrared spectrum analysis and nuclear magnetic resoance spectrum structural analysis, result is as follows:
Elementary 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 construction features of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds of the present invention It is: containing two stannum cores in molecule, and each tin atom is four-coordination distortion tetrahedral configuration.
A kind of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid esters as second aspect present invention Preparation method, reaction vessel is sequentially added into 5-nitroisophthalic acid, double [three (2-methyl-2-phenyl third in order Base) stannum] oxide and solvent methanol, react 8～24h under conditions of temperature is 50 ~ 65 DEG C；Cooling, filters, at 20 ~ 35 DEG C Under conditions of, control solvent volatilization crystallization, obtain white solid, be between double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitro Phthalic acid ester coordination compound.
In a preferred embodiment of the invention, described 5-nitroisophthalic acid, double [three (2-methyl-2-phenyl third Base) stannum] amount of material of both oxides is than for 1:(1 ~ 1.05).
In a preferred embodiment of the invention, described solvent methanol consumption is every mM of double [three (2-methyl-2- Phenyl propyl) stannum] oxide adds 30 ~ and 45 milliliters.
Double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid esters as third aspect present invention coordinate The application in preparing antitumor drug of the structure of thing.
Applicant has carried out anti tumor activity in vitro and has confirmed research above-mentioned coordination compound, confirms that this coordination compound has certain Anti-tumor biological, say, that the purposes of above-mentioned coordination compound is the application in preparing antitumor drug, the most just It it is the application in preparing anti-human lung-cancer medicament, human breast carcinoma, people's liver-cancer medicine.
Double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds of the present invention, to people's pulmonary carcinoma Medicine, human breast carcinoma, people's liver-cancer medicine etc. demonstrate good active anticancer, can prepare anti-lung cancer, anti-mammary gland with it for raw material Cancer, medicines resistant to liver cancer.Compared with the platinum-containing anticancer drug commonly used at present, double [three (2-methyl-2-phenyl) third of the present invention Ji Xi] 5-nitroisophthalic acid ester coordination compound has the features such as active anticancer height, low cost, preparation method are simple, for exploitation Cancer therapy drug provides new way.
Accompanying drawing explanation
Fig. 1 is the IR spectrogram of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.
Fig. 2 is double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds1H NMR spectra.
Fig. 3 is double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds13C NMR spectra.
Fig. 4 is double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds119Sn H NMR spectroscopy Figure.
Fig. 5 is the TG-DTG curve of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.
Detailed description of the invention
Further describe the present invention by following example, but it should be noted that the scope of the present invention is not implemented by these Any restriction of example.
Embodiment 1:
The preparation of double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound:
5-nitroisophthalic acid 0.2111g (1mmol), double [three (2-first it are sequentially added in order in 100ml round-bottomed flask Base-2-phenyl propyl) stannum] oxide 1.0532g (1mmol), solvent methanol 30mL are anti-under conditions of temperature is 50 ~ 65 DEG C Answer 8h；Cooling, filters, and under conditions of 20 ~ 35 DEG C, controls solvent volatilization crystallization, obtains white solid, be double [three (2-first Base-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.Productivity: 74%, fusing point: 139-140 DEG C.
Elementary 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 double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound:
5-nitroisophthalic acid 0.2116g (1mmol), double [three (2-first it are sequentially added in order in 100ml round-bottomed flask Base-2-phenyl propyl) stannum] oxide 1.1060g (1.05mmol), solvent methanol 47mL, under conditions of temperature is 50 ~ 65 DEG C Reaction 12h；Cooling, filters, and under conditions of 20 ~ 35 DEG C, controls solvent volatilization crystallization, obtains white solid, be double [three (2- Methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.Productivity: 76%, fusing point: 139-140 DEG C.
Elementary 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 double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound:
5-nitroisophthalic acid 0.4218g (2mmol), double [three (2-first it are sequentially added in order in 100ml round-bottomed flask Base-2-phenyl propyl) stannum] oxide 2.2112g (2.1mmol), solvent methanol 63mL, under conditions of temperature is 50 ~ 65 DEG C Reaction 18h；Cooling, filters, and under conditions of 20 ~ 35 DEG C, controls solvent volatilization crystallization, obtains white solid, be double [three (2- Methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.Productivity: 72%, fusing point: 139-140 DEG C.
Elementary 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 double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound:
5-nitroisophthalic acid 0.4221g (2mmol), double [three (2-first it are sequentially added in order in 100ml round-bottomed flask Base-2-phenyl propyl) stannum] oxide 2.1056 (2mmol), solvent methanol 70mL, under conditions of temperature is 50 ~ 65 DEG C react 24h；Cooling, filters, and under conditions of 20 ~ 35 DEG C, controls solvent volatilization crystallization, obtains white solid, be double [three (2-methyl- 2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.Productivity: 73%, fusing point: 139-140 DEG C.
Elementary 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 double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound:
5-nitroisophthalic acid 0.4223 (2mmol), double [three (2-first it are sequentially added in order in 100ml round-bottomed flask Base-2-phenyl propyl) stannum] oxide 2.1581g (2.05mmol), solvent methanol 70mL, under conditions of temperature is 50 ~ 65 DEG C Reaction 24h；Cooling, filters, and under conditions of 20 ~ 35 DEG C, controls solvent volatilization crystallization, obtains white solid, be double [three (2- Methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound.Productivity: 72%, fusing point: 139-140 DEG C.
Elementary 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: double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds of the present invention, its Anticancer Activity in vitro is measured and is realized by MTT experimental technique.
MTT analyses method: with metabolism reduction 3-(4,5-Dimethylthiazol-2-yl)-2,5- Based on diArenyltetrazolium bromide.Succinate dehydrogenase in living cells mitochondrion can make exogenous MTT It is reduced to water-insoluble bluish violet crystallization first a ceremonial jade-ladle, used in libation (Formazan) 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, measures the optical density of characteristic wavelength by microplate reader, can indirectly reflect living cells Quantity.
Mtt assay is used to measure double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compound pair Human lung carcinoma cell (NCI-H460), human breast cancer cell (MCF7), the inhibitory activity of human liver cancer cell (HepG2).
Cell strain and cultivating system: NCI-H460, MCF7 and HepG2 cell strain takes from American. tissue incubator (ATCC). By RPMI1640 (GIBICO company) culture medium containing 10% hyclone, at 5% (volume fraction) CO2, 37 DEG C of saturated humidity trainings In vitro culture is carried out in supporting case.
Test process: test medicinal liquid (0.1nM-10uM) is added separately in each hole according to the Concentraton gradient of concentration, Each concentration sets 6 parallel holes.Experiment is divided into drug test group (being separately added into the test medicine of variable concentrations), matched group (only to add Culture fluid and cell, be not added with testing medicine) and blank group (only adding culture fluid, be not added with cell and test medicine).By the orifice plate after dosing It is placed in 37 DEG C, 5%CO2Incubator is cultivated 72h.The activity of control drug measures according to the method for test sample.Cultivating In orifice plate after 72h, every hole adds MTT40uL (being made into 4mg/mL with D-Hanks buffer).After placing 4h at 37 DEG C, remove Clear liquid.Every hole adds 150uL DMSO, and vibrate 5min, makes Formazan crystallization dissolve.Finally, utilize automatic microplate reader at 570nm The optical density in each hole is detected at wavelength.
Data process: data process and use GraAr Pad Prism version5.0 program, compound IC50Pass through program In there is the nonlinear regression model (NLRM) of S-shaped dose response be fitted obtaining.
With MTT analytic process to human lung carcinoma cell (NCI-H460) cell strain, human breast cancer cell (MCF7) cell strain, people liver Cancerous cell (HepG2) cell strain is analyzed, and measures its IC50Value, result is as shown in table 1, and conclusion is: from data in table, The cancer therapy drug of the present invention, higher to people's pulmonary carcinoma, human breast carcinoma, people's hepatocarcinoma active anticancer, can candidates as cancer therapy drug Compound.
1 pair, table [three (2-methyl-2-phenyl) propyl group stannum] the 5-nitroisophthalic acid ester external work of coordination compound cancer therapy drug 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
Double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds prepared by remaining embodiment are with MTT The active anticancer of human lung carcinoma cell (NCI-H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7) is tested by method The same test example of method, test result is essentially identical with table 1.

Claims (8)

1. double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds, for following structural formula (I) coordination compound:
(I)。
2. double [three (2-methyl-2-phenyl) propyl group stannum] the 5-nitroisophthalic acid esters described in claim 1, its infrared number According to: IR (KBr, 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)；Its nuclear-magnetism modal data: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；Wherein, described double [three (2-methyl- 2-phenyl) propyl group stannum] in 5-nitroisophthalic acid ester molecule containing two stannum cores, and two tin atoms are four-coordination distortion Tetrahedral configuration.
3. the system of double [three (2-methyl-2-phenyl) propyl group stannum] the 5-nitroisophthalic acid ester coordination compounds described in claim 1 Preparation Method, it is characterised in that be sequentially added into 5-nitroisophthalic acid, double [three (2-methyl-2-in reaction vessel in order Phenyl propyl) stannum] oxide and solvent methanol, react 8～24h under conditions of temperature is 50 ~ 65 DEG C；Cooling, filters, 20 Under conditions of ~ 35 DEG C, control solvent volatilization crystallization, obtain white solid, be double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitre Base isophthalic acid ester.
4. preparation method as claimed in claim 3, it is characterised in that described 5-nitroisophthalic acid, double [three (2-methyl- 2-phenyl propyl) stannum] amount of material of both oxides is than for 1:(1 ~ 1.05).
5. preparation method as claimed in claim 3, it is characterised in that described solvent absolute methanol consumption is every mM of oxidation Double [three (2-methyl-2-phenyl) propyl group stannum] add 30 ~ and 45 milliliters.
6. described in claim 1, double [three (2-methyl-2-phenyl) propyl group stannum] 5-nitroisophthalic acid ester coordination compounds have one Fixed thermally-stabilised scope, can stable existence below 300 DEG C.
7. double [three (2-methyl-2-phenyl) propyl group stannum] the 5-nitroisophthalic acid ester coordination compounds described in claim 1 are in system Application in standby cancer therapy drug.
8. the application described in claim 6, wherein said cancer is pulmonary carcinoma, breast carcinoma, hepatocarcinoma.
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CN111057091A (en) * 2019-12-26 2020-04-24 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenyl) propyltin ] 5-aminoisophthalate complex
CN111057097A (en) * 2019-12-26 2020-04-24 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenyl) propyl tin ] 3-nitroisophthalate
CN111138484A (en) * 2019-12-26 2020-05-12 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenyl) propyl tin ] fumarate complex
CN111138488A (en) * 2019-12-26 2020-05-12 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenylpropyl) ] tin isophthalate complex

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CN111057091A (en) * 2019-12-26 2020-04-24 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenyl) propyltin ] 5-aminoisophthalate complex
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CN111057097B (en) * 2019-12-26 2023-04-14 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenyl) propyl tin ] 3-nitrophthalate complex
CN111057091B (en) * 2019-12-26 2023-05-05 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenyl) propyltin ] 5-amino isophthalic acid ester complex
CN111138484B (en) * 2019-12-26 2023-09-26 衡阳师范学院 Preparation method and application of bis [ tri (2-methyl-2-phenyl) propyltin ] fumarate complex

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