CN105646568A - 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex as well as preparation method and application thereof - Google Patents
2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN105646568A CN105646568A CN201610216380.1A CN201610216380A CN105646568A CN 105646568 A CN105646568 A CN 105646568A CN 201610216380 A CN201610216380 A CN 201610216380A CN 105646568 A CN105646568 A CN 105646568A
- Authority
- CN
- China
- Prior art keywords
- propionic acid
- coordination compound
- salicyloyl hydrazone
- acid salicyloyl
- stannous phenide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- C07F7/2284—Compounds with one or more Sn-N linkages
Abstract
The invention discloses a 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex. The complex adopts a structural formula (I) shown in the specification, wherein Ph is phenyl. The invention further discloses a preparation method of the 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex and an application of the 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex in preparation of anti-cancer drugs.
Description
Technical field
The present invention relates to a kind of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound and preparation method thereof and this 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound 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 first3SnOOCCH3The growth of mice cancerous cell is inhibited. 1980, the research of the chemists such as Crowe showed, many organo-tin compounds have anti tumor activity in vitro. 1989, more than 2,000 kinds of organo-tin compounds have been carried out antitumor activity screening by American National anticancer research institute (NationalCancerInstitute), and result shows that P388 Lymphocytic leukemia is had inhibitory action by some organo-tin compounds. 2002, Gielen et al., the activity of organotin carboxylate's ester compounds has been done comprehensive summing up, thought after research that many organo-tin compounds have good Anticancer Activity in vitro really.
Research shows, the organic group connected on organotin atom and the part participating in coordination decide the biological activity of organo-tin compound, select some itself to have the tin atom coordination in the organic ligand of good biological activity and organotin and cause the great interest of people. Acylhydrazone is the class Schiff compound modifiied by hydrazide kind compound, they are formed by aldehydes or ketones and hydrazides condensation, there is good biological activity, stronger coordination ability and various coordination mode, and have a wide range of applications in medicine, pesticide, material and analytical reagent etc. In recent years, it is compared in biological activity and in depth studies by domestic and international many research worker, and research finds that acylhydrazone has the various active such as anticancer, sterilization, antiinflammatory. Therefore, acylhydrazone class Schiff part is combined with organotin, it is intended to obtain the noval chemical compound that biological activity is higher, becomes the research direction that people are interested.
Chinese patent CN102718794A discloses a kind of pair of acylhydrazone class Schiff stannous phenide coordination compound and the application in the medicine preparing Antilung gland cancer, colon cancer, leukaemia thereof.
Chinese patent CN101851251A discloses the dibutyl tin coordination compound of a kind of acylhydrazone class Schiff part and treats the application in hepatocarcinoma, adenocarcinoma of lung, breast carcinoma, carcinoma of prostate, colon cancer or the morning young leukemic medicine of grain in preparation.
Document (JournalofOrganometallicChemistry, 2014,75:83-91) report, human colon cancer cell (HCT-116), human lung adenocarcinoma cell (A549), Human umbilical vein endothelial cells (HUVEC) are had relatively strong biological activity, and are better than carboplatin by organotin acylhydrazone class Schiff base complex.
Document (JournalofOrganometallicChemistry, 2013,724:23-31) report, series organotin acylhydrazone class Schiff base complex, organo-tin compound and acylhydrazone class Schiff part inhibitory action to cancerous cell such as human lung adenocarcinoma cell (A549), human colon cancer cell (HCT-8), people in loop (hl-60) respectively.
Document (Bioorganic&MedicinalChemistryLetters, 2015,25:4461-4463) is reported, the multiple acylhydrazone class Schiff part active anticancer to human liver cancer cell (HuH-7) and human lung adenocarcinoma cell (A549).
It is the material that the experiment proved that and there is active anticancer based on acylhydrazone class Schiff organotin complex, the present invention selects salicylyl hydrazine, Sodium Pyruvate and diphenyl stannum dichloride to react under certain condition, it is synthetically derived the coordination compound that 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) are had 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 propionic acid salicyloyl hydrazone stannous phenide coordination compound.
The second object of the present invention is to provide above-mentioned 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide 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 propionic acid salicyloyl hydrazone stannous phenide coordination compound.
As a kind of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of a first aspect of the present invention, for the coordination compound of structural formula (I)
(I)
Wherein Ph is phenyl.
The 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of the present invention is through elementary analysis, infrared spectrum and nuclear magnetic resoance spectrum structural analysis, and result is as follows:
Elementary analysis (C22H18N2O4Sn2): value of calculation: C53.59, H3.68, N5.68; Measured value: C53.54, H3.66, N5.69.
FT-IR(KBr,��/cm-1):3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,736,692,594,522,451��
1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz,1H),7.80-7.82(m,4H),7.44-7.52(m,7H),7.02-7.05(m,2H),2.58(s,3H)��
13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
Being structurally characterized in that of the 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of the present invention: in molecule, tin atom is hexa-coordinate distorted octahedron configuration.
The 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of the present invention has certain thermally-stabilised scope, can stable existence below 264 DEG C.
Preparation method as a kind of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of a second aspect of the present invention; the reaction vessel have nitrogen protection adds diphenyl stannum dichloride, salicylyl hydrazine, Sodium Pyruvate and solvent absolute methanol; 5 ~ 24h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; control solvent volatilization crystallization when 20 ~ 35 DEG C, obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound.
In a preferred embodiment of the invention, described diphenyl stannum dichloride, salicylyl hydrazine, Sodium Pyruvate three amount of substance 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 diphenyl stannum dichloride add 15 ~ 35 milliliters.
As the application in preparing cancer therapy drug of a kind of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of a third aspect of the present invention.
Above-mentioned 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound has been carried out anti tumor activity in vitro and has determined research by applicant, confirm 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound and there is certain anticancer bioactive, that is the purposes of above-mentioned coordination compound is the application in preparing cancer therapy drug, is exactly the application in preparing anti-human colon cancer, people's hepatocarcinoma, human breast carcinoma, human cervical carcinoma, people's lung-cancer medicament specifically.
Human colon cancer cell, human liver cancer cell, human breast cancer cell, human cervical carcinoma cell, human lung carcinoma cell etc. are demonstrated good active anticancer by the 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of the present invention, the features such as the 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound active anticancer of the present invention is high, cost is low, preparation method is simple, provide new way for developing new cancer therapy drug.
Accompanying drawing explanation
Fig. 1 is the IR spectrogram of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound.
Fig. 2 is 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound1HNMR spectrogram.
Fig. 3 is 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound13CNMR spectrogram.
Fig. 4 is the TG-DTG curve of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide 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 by any restriction of these embodiments.
Embodiment 1:
The preparation of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound:
The 100mL there-necked flask have nitrogen protection adds 0.344g (1.0mmol) diphenyl stannum dichloride, 0.152g (1.0mmol) salicylyl hydrazine, 0.121g (1.1mmol) Sodium Pyruvate and 25mL solvent absolute methanol; 8h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled when 20 ~ 35 DEG C; obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound. Productivity: 78.4%. Fusing point: 264 ~ 265 DEG C (dec).
Elementary analysis (C22H18N2O4Sn2): value of calculation: C53.59, H3.68, N5.68; Measured value: C53.54, H3.66, N5.69.
FT-IR(KBr,��/cm-1):3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,736,692,594,522,451��
1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz,1H),7.80-7.82(m,4H),7.44-7.52(m,7H),7.02-7.05(m,2H),2.58(s,3H)��
13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
Embodiment 2:
The preparation of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound:
The 100mL there-necked flask have nitrogen protection adds 0.344g (1.0mmol) diphenyl stannum dichloride, 0.152g (1.0mmol) salicylyl hydrazine, 0.116g (1.05mmol) Sodium Pyruvate and 35mL solvent absolute methanol; 5h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled when 20 ~ 35 DEG C; obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound. Productivity: 79.0%. Fusing point: 264 ~ 265 DEG C (dec).
Elementary analysis (C22H18N2O4Sn2): value of calculation: C53.59, H3.68, N5.68; Measured value: C53.54, H3.66, N5.69.
FT-IR(KBr,��/cm-1):3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,736,692,594,522,451��
1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz,1H),7.80-7.82(m,4H),7.44-7.52(m,7H),7.02-7.05(m,2H),2.58(s,3H)��
13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
Embodiment 3:
The preparation of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound:
The 100mL there-necked flask have nitrogen protection adds 0.344g (1.0mmol) diphenyl stannum dichloride, 0.160g (1.05mmol) salicylyl hydrazine, 0.127g (1.15mmol) Sodium Pyruvate and 30mL solvent absolute methanol; 15h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled when 20 ~ 35 DEG C; obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound. Productivity: 80.2%. Fusing point: 264 ~ 265 DEG C (dec).
Elementary analysis (C22H18N2O4Sn2): value of calculation: C53.59, H3.68, N5.68; Measured value: C53.54, H3.66, N5.69.
FT-IR(KBr,��/cm-1):3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,736,692,594,522,451��
1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz,1H),7.80-7.82(m,4H),7.44-7.52(m,7H),7.02-7.05(m,2H),2.58(s,3H)��
13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
Embodiment 4:
The preparation of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound:
The 250mL there-necked flask have nitrogen protection adds 1.720g (5.0mmol) diphenyl stannum dichloride, 0.775g (5.1mmol) salicylyl hydrazine, 0.594g (5.4mmol) Sodium Pyruvate and 100mL solvent absolute methanol; 20h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled when 20 ~ 35 DEG C; obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound. Productivity: 78.9%. Fusing point: 264 ~ 265 DEG C (dec).
Elementary analysis (C22H18N2O4Sn2): value of calculation: C53.59, H3.68, N5.68; Measured value: C53.54, H3.66, N5.69.
FT-IR(KBr,��/cm-1):3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,736,692,594,522,451��
1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz,1H),7.80-7.82(m,4H),7.44-7.52(m,7H),7.02-7.05(m,2H),2.58(s,3H)��
13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
Embodiment 5:
The preparation of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound:
The 250mL there-necked flask have nitrogen protection adds 1.720g (5.0mmol) diphenyl stannum dichloride, 0.790g (5.2mmol) salicylyl hydrazine, 0.616g (5.6mmol) Sodium Pyruvate and 150mL solvent absolute methanol; 22h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled when 20 ~ 35 DEG C; obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound. Productivity: 76.6%. Fusing point: 264 ~ 265 DEG C (dec).
Elementary analysis (C22H18N2O4Sn2): value of calculation: C53.59, H3.68, N5.68; Measured value: C53.54, H3.66, N5.69.
FT-IR(KBr,��/cm-1):3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,736,692,594,522,451��
1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz,1H),7.80-7.82(m,4H),7.44-7.52(m,7H),7.02-7.05(m,2H),2.58(s,3H)��
13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
Embodiment 6:
The preparation of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound:
The 250mL there-necked flask have nitrogen protection adds 3.440g (10.0mmol) diphenyl stannum dichloride, 1.550g (10.2mmol) salicylyl hydrazine, 1.166g (10.6mmol) Sodium Pyruvate and 150mL solvent absolute methanol; 24h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; solvent volatilization crystallization is controlled when 20 ~ 35 DEG C; obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound. Productivity: 75.1%. Fusing point: 264 ~ 265 DEG C (dec).
Elementary analysis (C22H18N2O4Sn2): value of calculation: C53.59, H3.68, N5.68; Measured value: C53.54, H3.66, N5.69.
FT-IR(KBr,��/cm-1):3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,736,692,594,522,451��
1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz,1H),7.80-7.82(m,4H),7.44-7.52(m,7H),7.02-7.05(m,2H),2.58(s,3H)��
13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
Test example:
The 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of the present invention, its Anticancer Activity in vitro is measured and is realized by MTT experiment method.
MTT analytic process:
Based on metabolism reduction 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazoliumbromide. Succinate dehydrogenase in living cells mitochondrion 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. First a ceremonial jade-ladle, used in libation in dimethyl sulfoxide (DMSO) energy dissolved cell, measures the optical density of characteristic wavelength, can indirectly reflect living cells quantity by microplate reader.
Mtt assay is adopted to measure the 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound of the embodiment 1 preparation inhibitory activity to human colon cancer cell (Colo205), human liver cancer cell (HepG2), human breast cancer cell (MCF7), human cervical carcinoma cell (Hela) and human lung carcinoma cell (NCI-H460).
Cell strain and cultivating system: Colo205, HepG2, MCF7, Hela and NCI-H460 cell strain take from American. tissue incubator (ATCC). RPMI1640(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: being added separately in each hole by test medicinal liquid (0.1ng/mL ~ 10ug/mL) according to the Concentraton 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), matched group (only adding culture fluid and cell, be not added with test 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 MTT40uL(D-Hanks buffer and is made into 4mg/mL).After placing 4h at 37 DEG C, remove the supernatant. Every hole adds 150uLDMSO, and vibrate 5min, makes Formazan crystallization dissolve. Finally, automatic microplate reader is utilized to detect the optical density in each hole at 570nm wavelength place.
Data process: data process and use GraphPadPrismversion5.0 program, coordination compound IC50It is fitted obtaining by program has the nonlinear regression model (NLRM) of S shape dose response.
With MTT analytic process, 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 strain 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 propionic acid salicyloyl hydrazone stannous phenide coordination compound 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 as the candidate compound of cancer therapy drug.
Table 12-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound cancer therapy drug external activity test data.
2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound prepared by all the other embodiments 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 propionic acid salicyloyl hydrazone stannous phenide coordination compound, for the coordination compound of following structural formula (I):
(I)
Wherein Ph is phenyl.
2. as claimed in claim 1 containing a kind of 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound, its ir data: FT-IR (KBr, ��/cm-1): 3456,3053,2989,1597,1517,1452,1328,1253,1220,1174,1087,7 36,692,594,522,451; Its nuclear-magnetism modal data:1HNMR(500MHz,CDCl3)��(ppm):11.43(s,1H),8.23(dd,J1=8.4Hz,J2=1.7Hz, 1H), 7.80-7.82 (m, 4H), 7.44-7.52 (m, 7H), 7.02-7.05 (m, 2H), 2.58 (s, 3H);13CNMR(125MHz,CDCl3)��(ppm):175.63,163.00,160.94,155.45,136.09,135.37,134.94,131.77,129.60,119.50,117.90,114.72,14.21��
3. described in claim 1,2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound has certain thermally-stabilised scope, can stable existence below 264 DEG C.
4. the preparation method of the 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound described in claim 1; it is characterized in that adding diphenyl stannum dichloride, salicylyl hydrazine, Sodium Pyruvate and solvent absolute methanol in the reaction vessel have nitrogen protection; 5 ~ 24h is reacted when temperature is 45 ~ 65 DEG C; cooling; filter; control solvent volatilization crystallization when 20 ~ 35 DEG C, obtain colourless transparent crystal, be 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound.
5. the method for preparation as claimed in claim 4, it is characterised in that described diphenyl stannum dichloride, salicylyl hydrazine, Sodium Pyruvate three amount of substance ratio 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 diphenyl stannum dichloride add 15 ~ 35 milliliters.
7. 2-carbonyl propionic acid salicyloyl hydrazone stannous phenide coordination compound application in preparing cancer therapy drug described in claim 1.
8. the application described in claim 7, wherein said cancerous cell is human colon cancer cell, human liver cancer cell, human breast cancer cell, human cervical carcinoma cell, human lung carcinoma cell.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610216380.1A CN105646568A (en) | 2016-04-11 | 2016-04-11 | 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610216380.1A CN105646568A (en) | 2016-04-11 | 2016-04-11 | 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex as well as preparation method and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105646568A true CN105646568A (en) | 2016-06-08 |
Family
ID=56497339
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610216380.1A Pending CN105646568A (en) | 2016-04-11 | 2016-04-11 | 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105646568A (en) |
Cited By (5)
| 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 |
| CN106220675A (en) * | 2016-08-28 | 2016-12-14 | 衡阳师范学院 | A kind of 2 carbonyl butanoic acid are to tert-butyl benzoyl hydrazone stannous phenide coordination compound and its preparation method and application |
| CN106279260A (en) * | 2016-08-20 | 2017-01-04 | 衡阳师范学院 | A kind of 2 carbonyl butanoic acid salicyloyl hydrazone di-n-butyl tin coordination compounds and its preparation method and application |
| CN106366120A (en) * | 2016-08-30 | 2017-02-01 | 衡阳师范学院 | 2-carbonyl butyric acid p-metoxybenzene formyl hydrazone diphenyl tin complex and preparation method and application thereof |
| CN106432322A (en) * | 2016-08-25 | 2017-02-22 | 衡阳师范学院 | 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060869A (en) * | 2010-12-14 | 2011-05-18 | 聊城大学 | Tindiphenyl (IV) coordination compound of benzoylformic acid-3-hydroxyl-2-naphthyl formyl hydrazone as well as preparation method and application thereof |
| CN105237562A (en) * | 2015-11-11 | 2016-01-13 | 衡阳师范学院 | 2-oxo propionic acid salicyloyl hydrazone tin diphenyl complex and preparation method and application thereof |
| CN105348318A (en) * | 2015-11-11 | 2016-02-24 | 衡阳师范学院 | 2-carbonyl butyric acid benzoyl hydrazone dibenzyl tin complex, preparation method therefor and applications |
-
2016
- 2016-04-11 CN CN201610216380.1A patent/CN105646568A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102060869A (en) * | 2010-12-14 | 2011-05-18 | 聊城大学 | Tindiphenyl (IV) coordination compound of benzoylformic acid-3-hydroxyl-2-naphthyl formyl hydrazone as well as preparation method and application thereof |
| CN105237562A (en) * | 2015-11-11 | 2016-01-13 | 衡阳师范学院 | 2-oxo propionic acid salicyloyl hydrazone tin diphenyl complex and preparation method and application thereof |
| CN105348318A (en) * | 2015-11-11 | 2016-02-24 | 衡阳师范学院 | 2-carbonyl butyric acid benzoyl hydrazone dibenzyl tin complex, preparation method therefor and applications |
Non-Patent Citations (1)
| Title |
|---|
| FOO I. P. P.等: "Synthesis and structural characterization of organotin(IV) complexes of pyruvic acid-4-hydroxybenzhydrazone (H4PDB): X-ray crystal structure of nBu2Sn(H2PDB)", 《ACGC CHEMICAL RESEARCH COMMUNICATIONS》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279260A (en) * | 2016-08-20 | 2017-01-04 | 衡阳师范学院 | A kind of 2 carbonyl butanoic acid salicyloyl hydrazone di-n-butyl tin coordination compounds and its preparation method and application |
| CN106279260B (en) * | 2016-08-20 | 2018-11-27 | 衡阳师范学院 | A kind of ALPHA-ketobutyric acid salicyloyl hydrazone di-n-butyl tin complex and its preparation method and application |
| CN106432322A (en) * | 2016-08-25 | 2017-02-22 | 衡阳师范学院 | 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin 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 |
| CN106220675A (en) * | 2016-08-28 | 2016-12-14 | 衡阳师范学院 | A kind of 2 carbonyl butanoic acid are to tert-butyl benzoyl hydrazone stannous phenide 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 |
| CN106366120A (en) * | 2016-08-30 | 2017-02-01 | 衡阳师范学院 | 2-carbonyl butyric acid p-metoxybenzene formyl hydrazone diphenyl tin complex and preparation method and application thereof |
| CN106366120B (en) * | 2016-08-30 | 2019-02-19 | 衡阳师范学院 | A kind of ALPHA-ketobutyric acid is to methoxybenzoyl hydrazone stannous phenide complex and its preparation method and application |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN105237563B (en) | A kind of 2 carbonyl propionic acid para hydroxybenzene formyl hydrazone two (2,4 dichloro benzyl) tin complexs and its preparation method and application | |
| CN105237564A (en) | 2-carbonyl-3-phenylpropionic acid salicylhydrazone bis(p-methylbenzyl)tin complex and preparation method and application thereof | |
| CN105693762A (en) | 2-carbonyl-2-phenylacetic acid benzoylhydrazone di-n-butyltin tin complex and preparation method and application thereof | |
| CN105646568A (en) | 2-oxo-propionic acid salicyloyl hydrazone diphenyltin complex as well as preparation method and application thereof | |
| CN105384770A (en) | 2-oxo-propionic acid salicyloyl hydrazone and di(p-methylbenzyl)tin complex as well as preparation method and application of 2-oxo-propionic acid salicyloyl hydrazone and di(p-methylbenzyl)tin complex | |
| CN105237562A (en) | 2-oxo propionic acid salicyloyl hydrazone tin diphenyl complex and preparation method and application thereof | |
| CN105348318A (en) | 2-carbonyl butyric acid benzoyl hydrazone dibenzyl tin complex, preparation method therefor and applications | |
| CN105753896A (en) | 2-carbonyl-3-phenylpropionic acid p-hydroxyphenylcarbonylhydrazone dibenzyl tin complex as well as preparation method and application thereof | |
| CN105541898B (en) | A kind of phenylpropionic acid benzoyl hydrazone two of 2 carbonyl 3 is to methyl-benzyl tin complex and its preparation method and application | |
| CN105601663A (en) | 2-carbonyl-2-phenyl acetic acid salicylyl hydrazone tindiphenyl complex, and preparation method and applications thereof | |
| CN105732698A (en) | 2-carbonyl-3-phenylpropionic acid salicyloyl hydrazone bi(2,4-dichloro benzyl) tin complex and preparation method and application thereof | |
| CN105777799A (en) | 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone dibenzyl tin complex as well as preparation method and application thereof | |
| CN105859768A (en) | 2-carbonyl-3-phenylpropionic acid salicylhydrazone dibenzyltin complex and preparation method and application thereof | |
| CN105693761A (en) | 2-carbonyl-3-phenylpropionic acid salicylacylhydrazone diphenyl tin complex as well as preparation method and application thereof | |
| CN105693763B (en) | A kind of organotin complex of the ligand containing acylhydrazone and its preparation method and application | |
| CN105399764B (en) | A kind of 2 carbonyl propionic acid benzoyl hydrazone Dibenzyltin complexs and its preparation method and application | |
| CN105884818A (en) | 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone diphenyltin complex and preparation method and application thereof | |
| CN106336427B (en) | A kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone two (2,4- dichloro benzyl) tin complex and its preparation method and application | |
| CN105399765B (en) | A kind of 2 carbonyl propionic acid benzoyl hydrazone tribenzyltin complexs and its preparation method and application | |
| CN106279261B (en) | A kind of di-n-butyl tin complex and its preparation method and application | |
| CN106432322A (en) | 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof | |
| CN106366118B (en) | A kind of 2- carbonyl -2- phenylacetic acid is to tert-butyl benzoyl hydrazone stannous phenide complex and its preparation method and application | |
| CN105777795A (en) | 5-chlorosalicylaldehyde contraction 4-nitro-o-aminophenol Schiff alkali diphenyl tin complex and preparing method and application thereof | |
| CN106336429B (en) | A kind of ALPHA-ketobutyric acid is to toluyl hydrazone stannous phenide complex and its preparation method and application | |
| CN106220676B (en) | A kind of 2- carbonyl propionic acids are to methoxybenzoyl hydrazone Dibenzyltin complex and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160608 |
|
| WD01 | Invention patent application deemed withdrawn after publication |