CN105753896A - 2-carbonyl-3-phenylpropionic acid p-hydroxyphenylcarbonylhydrazone dibenzyl tin complex as well as preparation method and application thereof - Google Patents

2-carbonyl-3-phenylpropionic acid p-hydroxyphenylcarbonylhydrazone dibenzyl tin complex as well as preparation method and application thereof Download PDF

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CN105753896A
CN105753896A CN201610216739.5A CN201610216739A CN105753896A CN 105753896 A CN105753896 A CN 105753896A CN 201610216739 A CN201610216739 A CN 201610216739A CN 105753896 A CN105753896 A CN 105753896A
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carbonyl
phenylpropionic acid
para hydroxybenzene
complex
formyl hydrazone
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CN201610216739.5A
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谭宇星
蒋伍玖
朱小明
冯泳兰
邝代治
张复兴
庾江喜
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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
    • C07F7/2284Compounds with one or more Sn-N linkages

Abstract

The invention discloses a 2-carbonyl-3-phenylpropionic acid p-hydroxyphenylcarbonylhydrazone dibenzyl tin complex which is a complex shown in the structural formula (I), wherein Ph is phenyl. The invention also discloses a preparation method of the 2-carbonyl-3-phenylpropionic acid p-hydroxyphenylcarbonylhydrazone dibenzyl tin complex and an application in preparation of anti-cancer drugs.

Description

A kind of 2- Carbonyl -3- Phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex and its preparation method and application

Technical field

The present invention relates to a kind of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex and preparation method thereof, and this 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex application in preparing cancer therapy drug.

Background technology

Organotin is the metallo-organic compound that a class contains Sn-C key.Researcher just noticed the Anticancer Activity in vitro of organo-tin compound before very early.1972, Brown found Ph first3SnOOCCH3Growth to mouse cancer cell is inhibited.1980, the research of the chemists such as Crowe showed, many organo-tin compounds have anti tumor activity in vitro.1989, American National anticancer research institute (National Cancer Institute) more than 2,000 kinds of organo-tin compounds have been carried out antitumor activity screening, result shows that some organo-tin compounds have inhibitory action to P388 lymphocytic leukemia.2002, the activity of organotin carboxylate's ester compounds was being done comprehensive summing up by Gielen et al., thought that many organo-tin compounds have preferable Anticancer Activity in vitro really after research.

Research shows, the organic group connected on organotin atom and the part participating in coordination decide the biologically active of organo-tin compound, select some tin atom coordinations having in the organic ligand of good biological activity and organotin itself to cause the great interest of people.Acylhydrazone is by a class of hydrazide kind compound modification Schiff alkali cpd, they are condensed by aldehydes or ketones and hydrazides and form, have good biologically active, stronger coordination ability and various coordination mode, and have a wide range of applications at aspects such as medicine, agricultural chemicals, material and analytical reagents.In recent years, both at home and abroad it is compared in terms of biologically active and in depth studies by many researchers, and research finds that acylhydrazone has the various active such as anticancer, sterilization, anti-inflammatory.Therefore, by acylhydrazone class Schiff Aar ligand is combined with organotin, it is intended to obtain the noval chemical compound that biologically active is higher, becomes the research direction that people are interested.

Chinese patent CN 102718794A discloses a kind of double acylhydrazone class Schiff alkali stannous phenide complex and the application in the medicine preparing Antilung gland cancer, colon cancer, leukaemia thereof.

Chinese patent CN 101851251A discloses a kind of acylhydrazone class The dibutyl tin complex of Schiff aar ligand and the application in preparation treatment liver cancer, adenocarcinoma of lung, breast cancer, prostate cancer, colon cancer or the youngest leukemic medicine of grain thereof.

Document (Journal of Organometallic Chemistry, 2014,75:83-91) report, organotin acylhydrazone class Schiff alkali complex has relatively strong biological activity to human colon cancer cell (HCT-116), human lung adenocarcinoma cell (A549), Human umbilical vein endothelial cells (HUVEC), and is better than carboplatin.

Document (Journal of Organometallic Chemistry, 2013,724:23-31) is reported, series organotin acylhydrazone class Schiff alkali complex, organo-tin compound and acylhydrazone class Schiff aar ligand inhibitory action to cancer cells such as human lung adenocarcinoma cell (A549), human colon cancer cell (HCT-8), people in loop (hl-60) respectively.

Document (Bioorganic & Medicinal Chemistry Letters, 2015,25: 4461-4463) report, multiple acylhydrazone class Schiff aar ligand is to human liver cancer cell (HuH-7) and the active anticancer of human lung adenocarcinoma cell (A549).

It is the material that the experiment proved that and there is active anticancer based on acylhydrazone class Schiff alkali organotin complex, the present invention selects para hydroxybenzene formylhydrazine, Sodium.beta.-phenylpyruvate to react under certain condition with TriphenylphosphineoxComplex, synthesis has obtained the complex to human colon cancer cell (Colo205), human liver cancer cell (HepG2), breast cancer cell (MCF7), cervical cancer cell (Hela) and human lung carcinoma cell (NCI-H460) with certain inhibitory activity, provides new approach for exploitation cancer therapy drug.

Summary of the invention

The first object of the present invention there is provided a kind of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.

The second object of the present invention is to provide above-mentioned 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex preparation method.

The third object of the present invention is to provide the application in preparing cancer therapy drug of the above-mentioned 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.

As a kind of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex of a first aspect of the present invention, for the complex of structure formula (I)

(I)

Wherein Ph is phenyl.

2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin the complex of the present invention is through elementary analysis, infrared spectrum and nuclear magnetic resoance spectrum structural analysis, and result is as follows:

Elementary analysis (C31H30N2O5Sn): calculated value: C 59.17, H 4.81, N 4.45;Measured value: C 59.24, H 4.76, N 4.42.

FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460。

1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H)。

13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。

Being structurally characterized in that of the 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex of the present invention: in molecule, tin atom is seven coordination distortion pentagonal bipyramid configurations.

2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin the complex of the present invention has certain thermally-stabilised scope, can stable existence below 184 DEG C.

Preparation method as a kind of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex of a second aspect of the present invention; TriphenylphosphineoxComplex, para hydroxybenzene formylhydrazine, Sodium.beta.-phenylpyruvate and solvent absolute methanol is added in the reaction vessel having nitrogen to protect; 5 ~ 24 h are reacted under conditions of temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C; obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.

In a preferred embodiment of the invention, the amount of the material of described TriphenylphosphineoxComplex, para hydroxybenzene formylhydrazine, Sodium.beta.-phenylpyruvate three is than for 1:(1 ~ 1.05): (1.05 ~ 1.15).

In a preferred embodiment of the invention, described solvent absolute methanol consumption be every mM of TriphenylphosphineoxComplex add 15 ~ 35 milliliters.

As the application in preparing cancer therapy drug of a kind of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex of a third aspect of the present invention.

Applicant has carried out anti tumor activity in vitro to above-mentioned 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex and has determined research, confirm 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex and there is certain anticancer bioactive, the purposes of the most above-mentioned complex is the application in preparing cancer therapy drug, is exactly the application in preparing anti-human colon cancer, people's liver cancer, human breast carcinoma, human cervical carcinoma, people's lung-cancer medicament specifically.

2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin the complex of the present invention demonstrates good active anticancer to human colon cancer cell, human liver cancer cell, human breast cancer cell, human cervical carcinoma cell, human lung carcinoma cell etc., the features such as the 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex active anticancer height of the present invention, low cost, preparation method are simple, provide new way for developing new cancer therapy drug.

Accompanying drawing explanation

Fig. 1 is the IR spectrogram of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.

Fig. 2 is 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex1H NMR spectra.

Fig. 3 is 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex13C NMR spectra.

Fig. 4 is the TG-DTG curve of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.

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 by any restriction of these embodiments.

Embodiment 1:

The preparation of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex:

0.372g is added in the 100mL there-necked flask having nitrogen to protect (1.0mmol) TriphenylphosphineoxComplex, 0.152g (1.0mmol) para hydroxybenzene formylhydrazine, 0.205g (1.1mmol) Sodium.beta.-phenylpyruvate and 25mL solvent absolute methanol, 8 h are reacted under conditions of temperature is 45 ~ 65 DEG C, cooling, filter, solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C, obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.Productivity: 86.8%.Fusing point: 184 ~ 186 DEG C (dec).

Elementary analysis (C31H30N2O5Sn): calculated value: C 59.17, H 4.81, N 4.45;Measured value: C 59.24, H 4.76, N 4.42.

FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460。

1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H)。

13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。

Embodiment 2:

The preparation of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex:

0.372g is added in the 100mL there-necked flask having nitrogen to protect (1.0mmol) TriphenylphosphineoxComplex, 0.152g (1.0mmol) para hydroxybenzene formylhydrazine, 0.195g (1.05mmol) Sodium.beta.-phenylpyruvate and 35mL solvent absolute methanol, 5 h are reacted under conditions of temperature is 45 ~ 65 DEG C, cooling, filter, solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C, obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.Productivity: 88.4%.Fusing point: 184 ~ 186 DEG C (dec).

Elementary analysis (C31H30N2O5Sn): calculated value: C 59.17, H 4.81, N 4.45;Measured value: C 59.24, H 4.76, N 4.42.

FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460。

1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H)。

13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。

Embodiment 3:

The preparation of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex:

0.372g is added in the 100mL there-necked flask having nitrogen to protect (1.0mmol) TriphenylphosphineoxComplex, 0.160g (1.05mmol) para hydroxybenzene formylhydrazine, 0.214g (1.15mmol) Sodium.beta.-phenylpyruvate and 30mL solvent absolute methanol, 15 h are reacted under conditions of temperature is 45 ~ 65 DEG C, cooling, filter, solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C, obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.Productivity: 89.9%.Fusing point: 184 ~ 186 DEG C (dec).

Elementary analysis (C31H30N2O5Sn): calculated value: C 59.17, H 4.81, N 4.45;Measured value: C 59.24, H 4.76, N 4.42.

FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460。

1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H)。

13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。

Embodiment 4:

The preparation of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex:

1.860g is added in the 250mL there-necked flask having nitrogen to protect (5.0mmol) TriphenylphosphineoxComplex, 0.775g (5.1mmol) para hydroxybenzene formylhydrazine, 1.004g (5.4mmol) Sodium.beta.-phenylpyruvate and 100mL solvent absolute methanol, 20 h are reacted under conditions of temperature is 45 ~ 65 DEG C, cooling, filter, solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C, obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.Productivity: 85.4%.Fusing point: 184 ~ 186 DEG C (dec).

Elementary analysis (C31H30N2O5Sn): calculated value: C 59.17, H 4.81, N 4.45;Measured value: C 59.24, H 4.76, N 4.42.

FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460。

1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H)。

13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。

Embodiment 5:

The preparation of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex:

1.860g is added in the 250mL there-necked flask having nitrogen to protect (5.0mmol) TriphenylphosphineoxComplex, 0.790g (5.2mmol) para hydroxybenzene formylhydrazine, 1.042g (5.6mmol) Sodium.beta.-phenylpyruvate and 150mL solvent absolute methanol, 22 h are reacted under conditions of temperature is 45 ~ 65 DEG C, cooling, filter, solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C, obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.Productivity: 87.6%.Fusing point: 184 ~ 186 DEG C (dec).

Elementary analysis (C31H30N2O5Sn): calculated value: C 59.17, H 4.81, N 4.45;Measured value: C 59.24, H 4.76, N 4.42.

FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460。

1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H)。

13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。

Embodiment 6:

The preparation of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex:

3.720g is added in the 250mL there-necked flask having nitrogen to protect (10.0mmol) TriphenylphosphineoxComplex, 1.550g (10.2mmol) para hydroxybenzene formylhydrazine, 1.972g (10.6mmol) Sodium.beta.-phenylpyruvate and 150mL solvent absolute methanol, 24 h are reacted under conditions of temperature is 45 ~ 65 DEG C, cooling, filter, solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C, obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.Productivity: 83.3%.Fusing point: 184 ~ 186 DEG C (dec).

Elementary analysis (C31H30N2O5Sn): calculated value: C 59.17, H 4.81, N 4.45;Measured value: C 59.24, H 4.76, N 4.42.

FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460。

1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H)。

13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。

Test example:

2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin the complex of the present invention, its Anticancer Activity in vitro is measured and is realized by MTT experiment method.

MTT analytic approach:

With metabolism reduction 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium Based on bromide.Succinate dehydrogenase in living cells mitochondria can make exogenous MTT be reduced to water-insoluble bluish violet crystallization 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) can dissolve the first a ceremonial jade-ladle, used in libation in cell, measures the optical density of characteristic wavelength with ELIASA, can indirectly reflect living cells quantity.

Mtt assay is used to measure the 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex of embodiment 1 preparation to human colon cancer cell (Colo205), human liver cancer cell (HepG2), human breast cancer cell (MCF7), human cervical carcinoma cell (Hela) and the inhibitory activity of human lung carcinoma cell (NCI-H460).

Cell line and cultivating system: Colo205, HepG2, MCF7, Hela and NCI-H460 cell line takes from American. tissue incubator (ATCC).RPMI 1640(GIBICO company with containing 10% hyclone) culture medium, in 5%(volume fraction) CO2, carry out in vitro culture in 37 DEG C of saturated humidity incubators.

Test process: test liquid (0.1ng/mL ~ 10ug/mL) being added separately in each hole according to the concentration gradient of concentration, each concentration sets 6 parallel holes.Experiment is divided into drug study group (being separately added into the test medicine of variable concentrations), control group (only adding nutrient solution and cell, be not added with testing medicine) and blank group (only adding cultivation medicine, be not added with cell and test medicine).Orifice plate after dosing is placed in 37 DEG C, 5%CO2Incubator is cultivated 72h.The activity of control drug measures according to the method for test sample.In orifice plate after having cultivated 72h, every hole adds MTT 40uL(D-Hanks buffer solution is made into 4mg/mL).After placing 4h at 37 DEG C, remove supernatant liquor.Every hole adds 150uL DMSO, and vibrate 5min, makes Formazan crystallization dissolve.Finally, automatic ELIASA is utilized to detect the optical density in each hole at 570nm wavelength.

Data process: data process and use Graph Pad Prism version 5.0 program, complex IC50It is fitted obtaining by program has the nonlinear regression model (NLRM) of S-shaped dose response.

With MTT analytic approach, 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 are analyzed, measure its IC50Value, result is as shown in table 1, conclusion is: from data in table, it is used as cancer therapy drug with the 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex of the present invention, 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) are had certain drug effect, can be as the candidate compound of cancer therapy drug.

Table 1 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex cancer therapy drug external activity test data.

2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex prepared by remaining embodiment is with the mtt assay same test example of active anticancer method of testing 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), and test result is essentially identical with table 1.

Claims (8)

1. a 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex, for the complex of following structure formula (I):
(I)
Wherein Ph is phenyl.
2. as claimed in claim 1 containing a kind of 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex, its ir data: FT-IR (KBr, ν/cm-1): 3296, 3061, 3026, 2808, 1641, 1589, 1492, 1386, 1168, 759, 696, 648, 592, 518, 460;Its nuclear-magnetism modal data:1H NMR (400 MHz, DMSO-d 6) δ(ppm): 9.98 (s, 1H), 7.77 (d,J = 7.31 Hz, 2H), 7.16 (m, 4H), 6.66-6.92 (m, 13H), 4.12 (s, 1H), 3.42 (s, 2H), 3.17(s, 3H), 2.81 (s, 4H);13C NMR (100 MHz, DMSO-d 6) δ(ppm): 172.94, 164.64, 160.34, 150.34, 138.62, 136.40, 129.94, 128.09, 127.97, 127.31, 125.74, 125.21, 123.95, 114.86, 48.62, 31.45。
3. described in claim 1,2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex has certain thermally-stabilised scope, can stable existence below 184 DEG C.
4. the preparation method of the 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex described in claim 1; it is characterized in that adding TriphenylphosphineoxComplex, para hydroxybenzene formylhydrazine, Sodium.beta.-phenylpyruvate and solvent absolute methanol in the reaction vessel having nitrogen to protect; 5 ~ 24 h are reacted under conditions of temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled under conditions of 20 ~ 35 DEG C; obtain orange colour transparent crystal, be 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex.
5. the method for preparation as claimed in claim 4, it is characterised in that described TriphenylphosphineoxComplex, para hydroxybenzene formylhydrazine, Sodium.beta.-phenylpyruvate three the amount ratio of material for 1:(1 ~ 1.05): (1.05 ~ 1.15).
6. the method for preparation as claimed in claim 4, it is characterised in that described solvent absolute methanol consumption be every mM of TriphenylphosphineoxComplex add 15 ~ 35 milliliters.
7. 2-carbonyl-3-phenylpropionic acid para hydroxybenzene formyl hydrazone Dibenzyltin complex application in preparing cancer therapy drug described in claim 1.
8. the application described in claim 7, wherein said cancer cell is human colon cancer cell, human liver cancer cell, human breast cancer cell, human cervical carcinoma cell, human lung carcinoma cell.
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106220676A (en) * 2016-08-28 2016-12-14 衡阳师范学院 A kind of 2 carbonyl propionic acids are to methoxybenzoyl hydrazone Dibenzyltin coordination compound and its preparation method and application
CN106220668A (en) * 2016-08-20 2016-12-14 衡阳师范学院 A kind of 2 carbonyl 3 phenylpropionic acid salicyloyl hydrazone di-n-butyl tin coordination compounds and its preparation method and application
CN106366117A (en) * 2016-08-24 2017-02-01 衡阳师范学院 2-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl tin complex, and preparation method and application thereof
CN106366114A (en) * 2016-08-22 2017-02-01 衡阳师范学院 2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin complex, and preparation method and application thereof
CN106366116A (en) * 2016-08-23 2017-02-01 衡阳师范学院 2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone di-p-methylbenzyltin complex, and preparation method and application thereof
CN106432324A (en) * 2016-08-29 2017-02-22 衡阳师范学院 2-carbonyl-3-phenylpropionic acid p-methoxybenzoyl hydrazone dibenzyl stannic complex as well as preparation method and application thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105198921A (en) * 2015-11-11 2015-12-30 衡阳师范学院 2-carbonyl-2-phenylacetic acid salicyloyl hydrazone dibutyltin complex as well as preparation method and application of 2-carbonyl-2-phenylacetic acid salicyloyl hydrazone dibutyltin complex
CN105237563A (en) * 2015-11-11 2016-01-13 衡阳师范学院 2-oxo propionic acid p-hydroxy benzoyl hydrazone bis(2,4-dichlorobenzyl) tin complex and preparation method and application thereof
CN105237564A (en) * 2015-11-11 2016-01-13 衡阳师范学院 2-carbonyl-3-phenylpropionic acid salicylhydrazone bis(p-methylbenzyl)tin complex and preparation method and application thereof
CN105399764A (en) * 2015-11-11 2016-03-16 衡阳师范学院 2-oxo-propionic acid benzoyl hydrazone dibenzyl tin complex as well as preparation method and application thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105198921A (en) * 2015-11-11 2015-12-30 衡阳师范学院 2-carbonyl-2-phenylacetic acid salicyloyl hydrazone dibutyltin complex as well as preparation method and application of 2-carbonyl-2-phenylacetic acid salicyloyl hydrazone dibutyltin complex
CN105237563A (en) * 2015-11-11 2016-01-13 衡阳师范学院 2-oxo propionic acid p-hydroxy benzoyl hydrazone bis(2,4-dichlorobenzyl) tin complex and preparation method and application thereof
CN105237564A (en) * 2015-11-11 2016-01-13 衡阳师范学院 2-carbonyl-3-phenylpropionic acid salicylhydrazone bis(p-methylbenzyl)tin complex and preparation method and application thereof
CN105399764A (en) * 2015-11-11 2016-03-16 衡阳师范学院 2-oxo-propionic acid benzoyl hydrazone dibenzyl tin complex as well as preparation method and application thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
冯泳兰等,: "2-羰基丙酸(芳甲酰基)腙二(2,4-二氯苄基)锡配合物的合成、晶体结构、热稳定性及与DNA相互作用研究", 《无机化学学报》 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106220668A (en) * 2016-08-20 2016-12-14 衡阳师范学院 A kind of 2 carbonyl 3 phenylpropionic acid salicyloyl hydrazone di-n-butyl tin coordination compounds and its preparation method and application
CN106220668B (en) * 2016-08-20 2018-09-14 衡阳师范学院 A kind of 2- carbonyls -3- phenylpropionic acids salicyloyl hydrazone di-n-butyl tin complex and its preparation method and application
CN106366114A (en) * 2016-08-22 2017-02-01 衡阳师范学院 2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone dibenzyltin complex, and preparation method and application thereof
CN106366116A (en) * 2016-08-23 2017-02-01 衡阳师范学院 2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone di-p-methylbenzyltin complex, and preparation method and application thereof
CN106366117A (en) * 2016-08-24 2017-02-01 衡阳师范学院 2-carbonyl-3-phenylpropionic-p-tert-butyl benzoyl hydrazone dibenzyl tin complex, and preparation method and application thereof
CN106220676A (en) * 2016-08-28 2016-12-14 衡阳师范学院 A kind of 2 carbonyl propionic acids are to methoxybenzoyl hydrazone Dibenzyltin coordination compound and its preparation method and application
CN106220676B (en) * 2016-08-28 2018-09-14 衡阳师范学院 A kind of 2- carbonyl propionic acids are to methoxybenzoyl hydrazone Dibenzyltin complex and its preparation method and application
CN106432324A (en) * 2016-08-29 2017-02-22 衡阳师范学院 2-carbonyl-3-phenylpropionic acid p-methoxybenzoyl hydrazone dibenzyl stannic complex as well as preparation method and application thereof

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