CN106220670A - A kind of 2 carbonyl 3 phenylpropionic acid p-nitrophenyl formyl hydrazones two are to methyl-benzyl stannum coordination compound and its preparation method and application - Google Patents
A kind of 2 carbonyl 3 phenylpropionic acid p-nitrophenyl formyl hydrazones two are to methyl-benzyl stannum coordination compound and its preparation method and application Download PDFInfo
- Publication number
- CN106220670A CN106220670A CN201610712384.9A CN201610712384A CN106220670A CN 106220670 A CN106220670 A CN 106220670A CN 201610712384 A CN201610712384 A CN 201610712384A CN 106220670 A CN106220670 A CN 106220670A
- Authority
- CN
- China
- Prior art keywords
- methyl
- carbonyl
- coordination compound
- phenylpropionic acid
- benzyl
- 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.)
- Granted
Links
- -1 carbonyl 3 phenylpropionic acid p-nitrophenyl formyl hydrazones Chemical class 0.000 title claims abstract description 103
- 150000001875 compounds Chemical class 0.000 title claims abstract description 63
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000003814 drug Substances 0.000 claims abstract description 21
- 229940079593 drug Drugs 0.000 claims abstract description 12
- 238000011275 oncology therapy Methods 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 14
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 206010006187 Breast cancer Diseases 0.000 claims description 11
- 208000026310 Breast neoplasm Diseases 0.000 claims description 11
- 239000013078 crystal Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
- 201000007270 liver cancer Diseases 0.000 claims description 8
- 208000014018 liver neoplasm Diseases 0.000 claims description 8
- MQGYVGKMCRDEAF-UHFFFAOYSA-M sodium;2-oxo-3-phenylpropanoate Chemical compound [Na+].[O-]C(=O)C(=O)CC1=CC=CC=C1 MQGYVGKMCRDEAF-UHFFFAOYSA-M 0.000 claims description 8
- 238000000902 119Sn nuclear magnetic resonance spectroscopy Methods 0.000 claims description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 201000005296 lung carcinoma Diseases 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 229910052718 tin Inorganic materials 0.000 claims description 3
- OBDMEACFKROVHP-UHFFFAOYSA-N N-amino-N-benzoylnitramide Chemical compound [N+](=O)([O-])N(N)C(C1=CC=CC=C1)=O OBDMEACFKROVHP-UHFFFAOYSA-N 0.000 claims 1
- FSQMMQKZAJETGN-UHFFFAOYSA-N n-amino-n-(4-nitrophenyl)formamide Chemical compound O=CN(N)C1=CC=C([N+]([O-])=O)C=C1 FSQMMQKZAJETGN-UHFFFAOYSA-N 0.000 claims 1
- 230000005311 nuclear magnetism Effects 0.000 claims 1
- 125000006178 methyl benzyl group Chemical group 0.000 abstract description 7
- 210000004027 cell Anatomy 0.000 description 37
- 230000001093 anti-cancer Effects 0.000 description 14
- 238000012360 testing method Methods 0.000 description 12
- 238000011160 research Methods 0.000 description 11
- FKZXYJYTUSGIQE-UHFFFAOYSA-N 4-nitrobenzohydrazide Chemical compound NNC(=O)C1=CC=C([N+]([O-])=O)C=C1 FKZXYJYTUSGIQE-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 206010009944 Colon cancer Diseases 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 208000029742 colonic neoplasm Diseases 0.000 description 4
- 238000002447 crystallographic data Methods 0.000 description 4
- 201000005249 lung adenocarcinoma Diseases 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 201000008275 breast carcinoma Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 3
- NSZRQCQXHMPQEY-UHFFFAOYSA-N C(=O)=C(C(=O)O)CC1=CC=CC=C1 Chemical compound C(=O)=C(C(=O)O)CC1=CC=CC=C1 NSZRQCQXHMPQEY-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 229910020813 Sn-C Inorganic materials 0.000 description 1
- 229910018732 Sn—C Inorganic materials 0.000 description 1
- 102000019259 Succinate Dehydrogenase Human genes 0.000 description 1
- 108010012901 Succinate Dehydrogenase Proteins 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- YAYRGNWWLMLWJE-UHFFFAOYSA-L carboplatin Chemical compound O=C1O[Pt](N)(N)OC(=O)C11CCC1 YAYRGNWWLMLWJE-UHFFFAOYSA-L 0.000 description 1
- 229960004562 carboplatin Drugs 0.000 description 1
- 208000019065 cervical carcinoma Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 1
- 229960004316 cisplatin Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- IXSZQYVWNJNRAL-UHFFFAOYSA-N etoxazole Chemical compound CCOC1=CC(C(C)(C)C)=CC=C1C1N=C(C=2C(=CC=CC=2F)F)OC1 IXSZQYVWNJNRAL-UHFFFAOYSA-N 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 208000003747 lymphoid leukemia Diseases 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
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 Table
- C07F7/22—Tin compounds
- C07F7/2284—Compounds with one or more Sn-N linkages
-
- 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 Table
- C07F7/22—Tin compounds
- C07F7/2296—Purification, stabilisation, isolation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention discloses a kind of 2 carbonyl 3 phenylpropionic acid p-nitrophenyl formyl hydrazones two to methyl-benzyl stannum coordination compound, for the coordination compound of following structure formula (I), wherein Ph is phenyl, and R is to methyl-benzyl.The invention also discloses this 2 carbonyl 3 phenylpropionic acid p-nitrophenyl formyl hydrazone two to the preparation method of methyl-benzyl stannum coordination compound and the application in preparing cancer therapy drug.
Description
Technical field
The present invention relates to a kind of 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl stannum coordination compound and
Preparation method, and this 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl stannum coordination compound prepare anticancer
Application in medicine.
Background technology
Organotin is the metallo-organic compound that a class contains Sn-C key.Researcher just noticed before very early
The Anticancer Activity in vitro of organo-tin compound.The research of organotin (IV) antitumor activity of compound can trace back to nineteen twenty-nine.
1967, Kanisawa etc. thought that stannic chloride is invalid to the primary tumor of mice and rat.But in 1972, Brown found,
By food or drug administration by injection, triphenyltin acetate Ph3SnOOCCH3Can suppress the tumor growth of mice, and triphenyltin chloride
Then can not.Between 1972 ~ 1977 years, Holland's substantial amounts of organo-tin compound of scholar's research, but find no further screening valency
The compound of value.They continue deeper into research, finally found that the tin compound of two organic group coordinations, such as tin-oxide
(R2SnO), stannum hydroxide ［ SnR2(OH) X ］ etc. have an anti-tumor activity, and find out that they all contain or hydrolyze and can produce stannum oxygen
Key.1980, Crowe etc. was found that again some organo-tin compounds have preferable active anticancer, from this, resisted about organotin
The research of cancer activity becomes another extremely active focus after cisplatin.1989, American National anticancer research institute
(National Cancer Institute) has carried out antitumor activity screening, result table to more than 2,000 kinds of organo-tin compounds
Brighter organo-tin compounds have inhibitory action to P388 Lymphocytic leukemia.2002, Gielen et al. was to organic
The activity of stannum carboxylate compound has done comprehensive summing up, thinks that many organo-tin compounds have the most external really after research
Active anticancer.
Research shows, the organic group that organotin atom connects and the part participating in coordination decide organo-tin compound
Biological activity, select some itself have good biological activity organic ligand with in organotin tin atom coordination cause
The great interest of people.Acylhydrazone is by a class Schiff compound of hydrazide kind compound modification, they
It is condensed by aldehydes or ketones and hydrazides and forms, molecule has the of bonding similar with peptide bond, there is good biological activity, stronger joining
Capability and various coordination mode, and have a wide range of applications at aspects such as medicine, pesticide, material and analytical reagents.Closely
Nian Lai, it is compared in terms of biological activity by the most many research worker in depth studies, and research finds acylhydrazone class
Compound 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, become the research direction that people are interested.
Chinese patent CN 102718794A discloses a kind of double acylhydrazone class Schiff stannous phenide coordination compound and in system
Standby Antilung gland cancer, colon cancer, leukaemia medicine in application.
Chinese patent CN 101851251A disclose a kind of acylhydrazone class Schiff part dibutyl tin coordination compound and
Application in preparation treatment hepatocarcinoma, adenocarcinoma of lung, breast carcinoma, carcinoma of prostate, colon cancer or the youngest leukemic medicine of grain.
Document (Journal of Organometallic Chemistry, 2014,75:83-91) is reported, organotin
Acylhydrazone class Schiff base complex is thin to human colon cancer cell (HCT-116), human lung adenocarcinoma cell (A549), human umblilical vein endothelial
Born of the same parents (HUVEC) have relatively strong biological activity, and are better than carboplatin.
Document (Journal of Organometallic Chemistry, 2013,724:23-31) is reported, series has
Machine stannum acylhydrazone class Schiff base complex, organo-tin compound and acylhydrazone class Schiff part are respectively to human lung adenocarcinoma cell
(A549), the inhibitory action of the cancerous cell such as human colon cancer cell (HCT-8), people in loop (hl-60).
Document (Bioorganic & Medicinal Chemistry Letters, 2015,25:4461-4463)
Report, multiple acylhydrazone class Schiff part is to human liver cancer cell (HuH-7) and the active anticancer of human lung adenocarcinoma cell (A549).
Document (Journal of Organometallic Chemistry, 2016,804:48-58) is reported, two hydrocarbon
Base stannum acylhydrazone class Schiff base complex is to human lung adenocarcinoma cell (A549), human cervical carcinoma cell (HeLa), human breast cancer cell
(MCF-7) inhibitory action of cancerous cell such as.
Being the material that the experiment proved that and have active anticancer based on acylhydrazone class Schiff organotin complex, the present invention selects
Selecting p-nitrobenzoylhydrazide, Sodium.beta.-phenylpyruvate and two pairs of methyl-benzyl stannum dichloride to react under certain condition, synthesis obtains
Human lung carcinoma cell (H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7) are had certain inhibitory activity join
Compound, 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 p-nitrophenyl formyl hydrazone two to methyl benzyl
Base stannum coordination compound.
The second object of the present invention is to provide above-mentioned 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl
Stannum coordination compound preparation method.
The third object of the present invention is to provide above-mentioned 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl
The application in preparing cancer therapy drug of the stannum coordination compound.
As a kind of 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two of a first aspect of the present invention to methyl-benzyl
Stannum coordination compound, for the coordination compound of structure formula (I)
(I)
Wherein Ph is phenyl, and R is to methyl-benzyl stannum.
Methyl-benzyl stannum coordination compound is divided by the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two of the present invention through element
Analysis, infrared spectrum, nuclear magnetic resoance spectrum and X-ray single crystal diffraction structural analysis, result is as follows:
Elementary analysis (C66H66N6O12Sn2): value of calculation: C 57.75, H 4.85, N 6.12；Measured value: C 57.80, H
4.84, N 6.11.
FT-IR (KBr, ν/cm-1): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525,
1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 815, 758,
711, 588, 561, 505, 459, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.30 (d, J =8.8 Hz, 2H), 8.09 (d, J =
8.8 Hz, 2H), 7.38 (d, J =7.7 Hz, 2H), 7.33 (t, J =7.7 Hz, 2H), 7.28 (d, J =
7.2 Hz, 1H), 6.67 (d, J =7.9 Hz, 4H), 6.62(d, J =7.9 Hz, 4H), 3.91 (s, 2H),
3.18 (d, J =11.7 Hz, 2H), 3.12 (d, J =11.7 Hz, 2H), 2.08 (s, 6H)。
13C NMR (126 MHz, CDCl3, δ/ppm): 172.94, 168.64, 153.45, 149.85,
139.11, 134.94, 134.80, 132.94, 129.91, 129.66, 128.88, 128.56, 128.12,
126.99, 123.20, 50.86, 36.66, 32.39, 20.87。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -636.93。
2-carbonyl-3-phenylpropionic acid p-nitrophenyl the formyl hydrazone two of the present invention is crystal knot to methyl-benzyl stannum coordination compound
Structure, its crystal is monoclinic system, space group P2 (1)/n, a=1.6255 (2) nm, b=1.20419 (17) nm, c=
1.7800 (2) nm, α=γ=90 °, β=112.560 (4) °, Z=4, V=3.2175 (8) nm3, Dc=1.417 Mg m-3, m (MoK α)=0.841 mm-1, F (000)=1400.
2-carbonyl-3-phenylpropionic acid p-nitrophenyl the formyl hydrazone two of the present invention construction features to methyl-benzyl stannum coordination compound
It is: in molecule, tin atom is seven coordination distortion pentagonal bipyramid configurations.
Methyl-benzyl stannum coordination compound is had certain by the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two of the present invention
Thermally-stabilised scope, can stable existence below 86 DEG C.
As a kind of 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two of a second aspect of the present invention to methyl-benzyl
The preparation method of stannum coordination compound, adds two to methyl-benzyl stannum dichloride, p-nitrophenyl in the reaction vessel having nitrogen to protect
Formylhydrazine, Sodium.beta.-phenylpyruvate and solvent absolute methanol, react 5 ~ 20 h, cooling under conditions of temperature is 50 ~ 65 DEG C, filter,
Under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization, obtain yellow transparent crystal, be 2-carbonyl-3-phenylpropionic acid to nitro
Benzoyl hydrazone two is to methyl-benzyl stannum coordination compound.
2-carbonyl-3-phenylpropionic acid p-nitrophenyl the formyl hydrazone two of the present invention preparation characteristic to methyl-benzyl stannum coordination compound
It is: from the relatively easy raw material being easy to get, without the separation of intermediate, directly obtain baroque molecule, i.e. one kettle way；
On such reaction economically and environmentally close friend advantageously.
In a preferred embodiment of the invention, described two pairs of methyl-benzyl stannum dichloride, p-nitrobenzoylhydrazide, benzene
The amount of the material of Sodium Pyruvate three is than for 1:(1 ~ 1.05): (1.05 ~ 1.15).
In a preferred embodiment of the invention, described solvent absolute methanol consumption is every mM of two pairs of methyl-benzyls
Stannum dichloride adds 15 ~ and 35 milliliters.
As a kind of 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two of a third aspect of the present invention to methyl-benzyl
The application in preparing cancer therapy drug of the stannum coordination compound.
Methyl-benzyl stannum coordination compound is carried out by applicant by above-mentioned 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two
Anticancer Activity in vitro determines research, it is thus identified that methyl-benzyl stannum is coordinated by 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two
Thing has certain anticancer bioactive, say, that the purposes of above-mentioned coordination compound is the application in preparing cancer therapy drug, tool
Saying of body is exactly the application in preparing anti-human pulmonary carcinoma, people's hepatocarcinoma and human breast carcinoma medicine.
2-carbonyl-3-phenylpropionic acid p-nitrophenyl the formyl hydrazone two of the present invention is thin to people's pulmonary carcinoma to methyl-benzyl stannum coordination compound
Born of the same parents, human liver cancer cell and human breast cancer cell demonstrate good active anticancer, and the 2-carbonyl-3-phenylpropionic acid of the present invention is to nitre
Base benzoyl hydrazone two is to features such as methyl-benzyl stannum coordination compound active anticancer height, low cost, preparation method are simple, new for exploitation
Cancer therapy drug provides new way.
Accompanying drawing explanation
Fig. 1 is the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two IR spectrogram to methyl-benzyl stannum coordination compound.
Fig. 2 is that 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two is to methyl-benzyl stannum coordination compound1H NMR spectra.
Fig. 3 is that 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two is to methyl-benzyl stannum coordination compound13C NMR spectra.
Fig. 4 is that 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two is to methyl-benzyl stannum coordination compound119Sn H NMR spectroscopy
Figure.
Fig. 5 is the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two crystal structure figure to methyl-benzyl stannum coordination compound.
Fig. 6 is the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two TG-DTG curve to methyl-benzyl stannum coordination compound.
Detailed description of the invention
By detailed description below, the present invention is described in further detail.
Embodiment 1:
The preparation to methyl-benzyl stannum coordination compound of the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two:
In the 100mL there-necked flask having nitrogen to protect add 0.400g (1.0mmol) two pairs of methyl-benzyl stannum dichloride,
0.181g (1.0mmol) p-nitrobenzoylhydrazide, 0.195g (1.05mmol) Sodium.beta.-phenylpyruvate and 15mL solvent absolute methanol,
8 h are reacted under conditions of temperature is 50 ~ 65 DEG C, cooling, filter, under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization,
Yellow transparent crystal, is 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl stannum coordination compound.Productivity:
70.6%.Fusing point: 86 ~ 88 DEG C (dec).
Elementary analysis (C66H66N6O12Sn2): value of calculation: C 57.75, H 4.85, N 6.12；Measured value: C 57.80, H
4.84, N 6.11.
FT-IR (KBr, ν/cm-1): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525,
1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 815, 758,
711, 588, 561, 505, 459, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.30 (d, J =8.8 Hz, 2H), 8.09 (d, J =
8.8 Hz, 2H), 7.38 (d, J =7.7 Hz, 2H), 7.33 (t, J =7.7 Hz, 2H), 7.28 (d, J =
7.2 Hz, 1H), 6.67 (d, J =7.9 Hz, 4H), 6.62(d, J =7.9 Hz, 4H), 3.91 (s, 2H),
3.18 (d, J =11.7 Hz, 2H), 3.12 (d, J =11.7 Hz, 2H), 2.08 (s, 6H)。
13C NMR (126 MHz, CDCl3, δ/ppm): 172.94, 168.64, 153.45, 149.85,
139.11, 134.94, 134.80, 132.94, 129.91, 129.66, 128.88, 128.56, 128.12,
126.99, 123.20, 50.86, 36.66, 32.39, 20.87。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -636.93。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.6255 (2) nm, b=1.20419 (17) nm,
C=1.7800 (2) nm, α=γ=90 °, β=112.560 (4) °, Z=4, V=3.2175 (8) nm3, Dc=1.417
Mg·m-3, m (MoK α)=0.841 mm-1, F (000)=1400.
Embodiment 2:
The preparation to methyl-benzyl stannum coordination compound of the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two:
In the 100mL there-necked flask having nitrogen to protect add 0.400g (1.0mmol) two pairs of methyl-benzyl stannum dichloride,
0.190g (1.05mmol) p-nitrobenzoylhydrazide, 0.214g (1.15mmol) Sodium.beta.-phenylpyruvate and 35mL solvent are without water beetle
Alcohol, reacts 5 h under conditions of temperature is 50 ~ 65 DEG C, cooling, filters, and controls solvent volatilization knot under conditions of 20 ~ 35 DEG C
Crystalline substance, obtains yellow transparent crystal, is 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl stannum coordination compound.Produce
Rate: 73.3%.Fusing point: 86 ~ 88 DEG C (dec).
Elementary analysis (C66H66N6O12Sn2): value of calculation: C 57.75, H 4.85, N 6.12；Measured value: C 57.80, H
4.84, N 6.11.
FT-IR (KBr, ν/cm-1): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525,
1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 815, 758,
711, 588, 561, 505, 459, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.30 (d, J =8.8 Hz, 2H), 8.09 (d, J =
8.8 Hz, 2H), 7.38 (d, J =7.7 Hz, 2H), 7.33 (t, J =7.7 Hz, 2H), 7.28 (d, J =
7.2 Hz, 1H), 6.67 (d, J =7.9 Hz, 4H), 6.62(d, J =7.9 Hz, 4H), 3.91 (s, 2H),
3.18 (d, J =11.7 Hz, 2H), 3.12 (d, J =11.7 Hz, 2H), 2.08 (s, 6H)。
13C NMR (126 MHz, CDCl3, δ/ppm): 172.94, 168.64, 153.45, 149.85,
139.11, 134.94, 134.80, 132.94, 129.91, 129.66, 128.88, 128.56, 128.12,
126.99, 123.20, 50.86, 36.66, 32.39, 20.87。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -636.93。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.6255 (2) nm, b=1.20419 (17) nm,
C=1.7800 (2) nm, α=γ=90 °, β=112.560 (4) °, Z=4, V=3.2175 (8) nm3, Dc=1.417
Mg·m-3, m (MoK α)=0.841 mm-1, F (000)=1400.
Embodiment 3:
The preparation to methyl-benzyl stannum coordination compound of the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two:
In the 100mL there-necked flask having nitrogen to protect add 2.000g (5.0mmol) two pairs of methyl-benzyl stannum dichloride,
0.923g (5.1mmol) p-nitrobenzoylhydrazide, 1.023g (5.5mmol) Sodium.beta.-phenylpyruvate and 25mL solvent absolute methanol,
20 h are reacted under conditions of temperature is 50 ~ 65 DEG C, cooling, filter, under conditions of 20 ~ 35 DEG C, control solvent volatilization crystallization,
Obtain yellow transparent crystal, be 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl stannum coordination compound.Productivity:
74.5%.Fusing point: 86 ~ 88 DEG C (dec).
Elementary analysis (C66H66N6O12Sn2): value of calculation: C 57.75, H 4.85, N 6.12；Measured value: C 57.80, H
4.84, N 6.11.
FT-IR (KBr, ν/cm-1): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525,
1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 815, 758,
711, 588, 561, 505, 459, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.30 (d, J =8.8 Hz, 2H), 8.09 (d, J =
8.8 Hz, 2H), 7.38 (d, J =7.7 Hz, 2H), 7.33 (t, J =7.7 Hz, 2H), 7.28 (d, J =
7.2 Hz, 1H), 6.67 (d, J =7.9 Hz, 4H), 6.62(d, J =7.9 Hz, 4H), 3.91 (s, 2H),
3.18 (d, J =11.7 Hz, 2H), 3.12 (d, J =11.7 Hz, 2H), 2.08 (s, 6H)。
13C NMR (126 MHz, CDCl3, δ/ppm): 172.94, 168.64, 153.45, 149.85,
139.11, 134.94, 134.80, 132.94, 129.91, 129.66, 128.88, 128.56, 128.12,
126.99, 123.20, 50.86, 36.66, 32.39, 20.87。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -636.93。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.6255 (2) nm, b=1.20419 (17) nm,
C=1.7800 (2) nm, α=γ=90 °, β=112.560 (4) °, Z=4, V=3.2175 (8) nm3, Dc=1.417
Mg·m-3, m (MoK α)=0.841 mm-1, F (000)=1400.
Embodiment 4:
The preparation to methyl-benzyl stannum coordination compound of the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two:
In the 500mL there-necked flask having nitrogen to protect add 4.000g (10.0mmol) two pairs of methyl-benzyl stannum dichloride,
1.864g (10.3mmol) p-nitrobenzoylhydrazide, 2.046g (11.0mmol) Sodium.beta.-phenylpyruvate and 200mL solvent are without water beetle
Alcohol, reacts 16 h under conditions of temperature is 50 ~ 65 DEG C, cooling, filters, and controls solvent volatilization knot under conditions of 20 ~ 35 DEG C
Crystalline substance, obtains yellow transparent crystal, is 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two to methyl-benzyl stannum coordination compound.Produce
Rate: 72.1%.Fusing point: 86 ~ 88 DEG C (dec).
Elementary analysis (C66H66N6O12Sn2): value of calculation: C 57.75, H 4.85, N 6.12；Measured value: C 57.80, H
4.84, N 6.11.
FT-IR (KBr, ν/cm-1): 3566, 3022, 2918, 2860, 1637, 1618, 1597, 1525,
1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858, 815, 758,
711, 588, 561, 505, 459, 418。
1H NMR (500 MHz, CDCl3, δ/ppm): 8.30 (d, J =8.8 Hz, 2H), 8.09 (d, J =
8.8 Hz, 2H), 7.38 (d, J =7.7 Hz, 2H), 7.33 (t, J =7.7 Hz, 2H), 7.28 (d, J =
7.2 Hz, 1H), 6.67 (d, J =7.9 Hz, 4H), 6.62(d, J =7.9 Hz, 4H), 3.91 (s, 2H),
3.18 (d, J =11.7 Hz, 2H), 3.12 (d, J =11.7 Hz, 2H), 2.08 (s, 6H)。
13C NMR (126 MHz, CDCl3, δ/ppm): 172.94, 168.64, 153.45, 149.85,
139.11, 134.94, 134.80, 132.94, 129.91, 129.66, 128.88, 128.56, 128.12,
126.99, 123.20, 50.86, 36.66, 32.39, 20.87。
119Sn NMR (187 MHz, CDCl3, δ/ppm): -636.93。
Crystallographic data: monoclinic system, space group P2 (1)/n, a=1.6255 (2) nm, b=1.20419 (17) nm,
C=1.7800 (2) nm, α=γ=90 °, β=112.560 (4) °, Z=4, V=3.2175 (8) nm3, Dc=1.417
Mg·m-3, m (MoK α)=0.841 mm-1, F (000)=1400.
Test example:
2-carbonyl-3-phenylpropionic acid p-nitrophenyl the formyl hydrazone two of the present invention to methyl-benzyl stannum coordination compound, its external anticancer work
Property measure realized by MTT experiment method.
MTT analytic process:
With metabolism reduction 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide it is
Basis.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.Dimethyl sulfoxide (DMSO) can dissolve the first a ceremonial jade-ladle, used in libation in cell,
Measure the optical density of characteristic wavelength by microplate reader, can indirectly reflect living cells quantity.
Mtt assay is used to measure the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two of embodiment 1 preparation to methyl benzyl
Base stannum coordination compound is to human lung carcinoma cell (H460), human liver cancer cell (HepG2) and the inhibitory activity of human breast cancer cell (MCF7).
Cell strain and cultivating system: H460, HepG2 and MCF7 cell strain takes from American. tissue incubator (ATCC).With containing
RPMI 1640 (GIBICO company) culture medium of 10% hyclone, at 5% (volume fraction) CO2, 37 DEG C of saturated humidity incubators
Inside carry out In vitro culture.
Test process: test medicinal liquid (1nM ~ 10 μM) is added separately in each hole according to the Concentraton gradient of concentration, often
Individual 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 to add training
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 put
In 37 DEG C, 5%CO2Incubator is cultivated 72h.The activity of control drug measures according to the method for test sample.Cultivating 72h
After orifice plate in, every hole adds MTT 40 μ L (being made into 4mg/mL with D-Hanks buffer).After placing 4h at 37 DEG C, remove upper strata
Clear liquid.Every hole adds 150 μ L 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 Graph Pad Prism version 7.0 program, coordination compound IC50Pass through journey
The nonlinear regression model (NLRM) in sequence with S-shaped dose response is fitted obtaining.
Thin to human lung carcinoma cell (H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7) with MTT analytic process
Born of the same parents' strain is analyzed, and measures its IC50Value, result is as shown in table 1, and conclusion is: from data in table, with the 2-carbonyl of the present invention
Base-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two is used as cancer therapy drug to methyl-benzyl stannum coordination compound, to human lung carcinoma cell
(H460), human liver cancer cell (HepG2) and human breast cancer cell (MCF7) there is certain drug effect, can be as the time of cancer therapy drug
Select compound.
Table 1 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two is to the methyl-benzyl stannum external work of coordination compound cancer therapy drug
Property test data.
| People's pulmonary carcinoma | People's hepatocarcinoma | Human breast carcinoma | |
| Cell strain | H460 | HepG2 | MCF7 |
| IC50(μM) | 7.29±1.36 | 4.64±1.62 | 5.00±1.47 |
2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two prepared by remaining embodiment to methyl-benzyl stannum coordination compound with
Mtt assay is to human lung carcinoma cell (H460), human liver cancer cell (HepG2) and the active anticancer test side of human breast cancer cell (MCF7)
The same test example of method, test result is essentially identical with table 1.
These are only the preferred embodiments of the present invention and test example, be not limited to the present invention, it is clear that the skill of this area
Art personnel can carry out various change, modification without departing from the spirit and scope of the present invention to the present invention.If to the present invention's
These amendments and modification belong within the scope of the claims in the present invention and equivalent technologies thereof, belong to the protection model of the present invention
Enclose.
Claims (9)
1. 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two is to a methyl-benzyl stannum coordination compound, for following structure formula (I)
Coordination compound:
(I)
Wherein Ph is phenyl, and R is to methyl-benzyl stannum.
2. the one 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two that contains as claimed in claim 1 is to methyl-benzyl stannum
Coordination compound, its ir data: FT-IR (KBr, ν/cm-1): 3566, 3022, 2918, 2860, 1637, 1618,
1597, 1525, 1492, 1386, 1338, 1317, 1226, 1170, 1134, 1105, 1014, 894, 858,
815, 758, 711, 588, 561, 505, 459, 418；Its nuclear-magnetism modal data:1H NMR (500 MHz, CDCl3, δ/
ppm): 8.30 (d, J =8.8 Hz, 2H), 8.09 (d, J =8.8 Hz, 2H), 7.38 (d, J =7.7 Hz,
2H), 7.33 (t, J =7.7 Hz, 2H), 7.28 (d, J =7.2 Hz, 1H), 6.67 (d, J =7.9 Hz,
4H), 6.62(d, J =7.9 Hz, 4H), 3.91 (s, 2H), 3.18 (d, J =11.7 Hz, 2H), 3.12 (d, J=11.7 Hz, 2H), 2.08 (s, 6H)；13C NMR (126 MHz, CDCl3, δ/ppm): 172.94, 168.64,
153.45, 149.85, 139.11, 134.94, 134.80, 132.94, 129.91, 129.66, 128.88,
128.56, 128.12, 126.99, 123.20, 50.86, 36.66, 32.39, 20.87；119Sn NMR (187 MHz,
CDCl3, δ/ppm): -636.93。
3. 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two as claimed in claim 1 is to methyl-benzyl stannum coordination compound,
Wherein, described 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two is crystal structure to methyl-benzyl stannum coordination compound, and it is brilliant
Body data are as follows: monoclinic system, space group P2 (1)/n, a=1.6255 (2) nm, and b=1.20419 (17) nm, c=
1.7800 (2) nm, α=γ=90 °, β=112.560 (4) °, Z=4, V=3.2175 (8) nm3, Dc=1.417 Mg m-3, m (MoK α)=0.841 mm-1, F (000)=1400；In molecule, tin atom is seven coordination distortion pentagonal bipyramid configurations.
4. described in claim 1,2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two has one to methyl-benzyl stannum coordination compound
Fixed thermally-stabilised scope, can stable existence below 86 DEG C.
5. the system to methyl-benzyl stannum coordination compound of the 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two described in claim 1
Preparation Method, is characterized in that adding two in the reaction vessel having nitrogen to protect to methyl-benzyl stannum dichloride, p-nitrophenyl formyl
Hydrazine, Sodium.beta.-phenylpyruvate and solvent absolute methanol, react 5 ~ 20 h, cooling under conditions of temperature is 50 ~ 65 DEG C, filter, 20 ~
Control solvent volatilization crystallization under conditions of 35 DEG C, obtain yellow transparent crystal, be 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl
Hydrazone two is to methyl-benzyl stannum coordination compound.
6. the method for preparation as claimed in claim 5, it is characterised in that described two pairs of methyl-benzyl stannum dichloride, to nitro
Benzoyl hydrazine, Sodium.beta.-phenylpyruvate three the amount of material than for 1:(1 ~ 1.05): (1.05 ~ 1.15).
7. the method for preparation as claimed in claim 5, it is characterised in that described solvent absolute methanol consumption is every mM two
Methyl-benzyl stannum dichloride is added 15 ~ 35 milliliters.
8. methyl-benzyl stannum coordination compound is being prepared by 2-carbonyl-3-phenylpropionic acid p-nitrophenyl formyl hydrazone two described in claim 1
Application in cancer therapy drug.
9. the application described in claim 8, wherein said cancerous cell is human lung carcinoma cell, human liver cancer cell, human breast cancer cell.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610712384.9A CN106220670B (en) | 2016-08-23 | 2016-08-23 | Two pairs of methylbenzyl tin complexs of one kind and its preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610712384.9A CN106220670B (en) | 2016-08-23 | 2016-08-23 | Two pairs of methylbenzyl tin complexs of one kind and its preparation method and application |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106220670A true CN106220670A (en) | 2016-12-14 |
| CN106220670B CN106220670B (en) | 2018-09-14 |
Family
ID=57554018
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610712384.9A Active CN106220670B (en) | 2016-08-23 | 2016-08-23 | Two pairs of methylbenzyl tin complexs of one kind and its preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106220670B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN105541898A (en) * | 2015-11-11 | 2016-05-04 | 衡阳师范学院 | Benzoylhydrazone bis(p-methylbenzyl) tin 2-carbonyl-3-phenylpropionate complex, and preparation method and application thereof |
| CN105777799A (en) * | 2016-04-22 | 2016-07-20 | 衡阳师范学院 | 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone dibenzyl tin complex as well as preparation method and application thereof |
| CN105859768A (en) * | 2016-04-23 | 2016-08-17 | 衡阳师范学院 | 2-carbonyl-3-phenylpropionic acid salicylhydrazone dibenzyltin complex and preparation method and application thereof |
-
2016
- 2016-08-23 CN CN201610712384.9A patent/CN106220670B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN105541898A (en) * | 2015-11-11 | 2016-05-04 | 衡阳师范学院 | Benzoylhydrazone bis(p-methylbenzyl) tin 2-carbonyl-3-phenylpropionate complex, and preparation method and application thereof |
| CN105777799A (en) * | 2016-04-22 | 2016-07-20 | 衡阳师范学院 | 2-carbonyl-3-phenylpropionic acid benzoyl hydrazone dibenzyl tin complex as well as preparation method and application thereof |
| CN105859768A (en) * | 2016-04-23 | 2016-08-17 | 衡阳师范学院 | 2-carbonyl-3-phenylpropionic acid salicylhydrazone dibenzyltin complex and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106220670B (en) | 2018-09-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106432323A (en) | 2-carbonyl butyric acid p-methoxy benzoyl hydrazone di-n-butyltin complex and preparation method and application thereof | |
| CN106336427A (en) | 2-carbonyl-2-phenyl acetic acid p-nitrobenzoylhydrazone bis(2,4-dichlorobenzyl)tin complex and preparation method and application thereof | |
| CN106366113A (en) | 2-oxo-propionic acid p-toluyl hydrazone di-2, 4-dichlorobenzyltin complex and its preparation method and use | |
| CN106220669B (en) | A kind of dialkyl tin complex of the ligand containing acylhydrazone and its preparation method and application | |
| CN106336430A (en) | 2-oxo-butyric acid p-methyl benzoyl hydrazone di-n-butyl tin complex and preparation method and application thereof | |
| CN106432322A (en) | 2-Carbonyl-2-phenylacetic acid p-nitrobenzoyl hydrazone diphenyltin complex, and preparation method and application thereof | |
| CN106220670A (en) | A kind of 2 carbonyl 3 phenylpropionic acid p-nitrophenyl formyl hydrazones two are to methyl-benzyl stannum coordination compound and its preparation method and application | |
| CN106380480B (en) | A kind of ALPHA-ketobutyric acid p-nitrophenyl formyl hydrazone stannous phenide complex and its preparation method and application | |
| CN106317105B (en) | A kind of 2- carbonyl -2- phenylacetic acid p-nitrophenyl formyl hydrazone di-n-butyl tin complex and its preparation method and application | |
| CN106336426A (en) | 2-carbonyl-2-phenyl acetic acid p-nitrobenzoylhydrazone bis(p-methylbenzyl)tin complex and preparation method and application thereof | |
| CN106220674A (en) | A kind of 2 carbonyl butanoic acid salicyloyl hydrazone Dibenzyltin coordination compounds and its preparation method and application | |
| CN106366116A (en) | 2-Oxo-3-phenylpropionic acid p-methylbenzoyl hydrazone di-p-methylbenzyltin complex, and preparation method and application thereof | |
| CN106279250A (en) | A kind of 2 carbonyl 3 phenylpropionic acid para hydroxybenzene formyl hydrazone stannous phenide coordination compounds and its preparation method and application | |
| CN106220678A (en) | A kind of 2 carbonyl propionic acid p-nitrophenyl formyl hydrazones two are to methyl-benzyl stannum coordination compound and its preparation method and application | |
| CN106279252A (en) | A kind of 2 carbonyl 3 phenylpropionic acid benzoyl hydrazone di-n-butyl tin coordination compounds and its preparation method and application | |
| CN106279262A (en) | A kind of 2 carbonyl 3 phenylpropionic acids are to toluyl hydrazone two (2,4 dichloro benzyl) stannum coordination compound and its preparation method and application | |
| CN106279261A (en) | A kind of 2 carbonyl 3 phenylpropionic acids are to toluyl hydrazone di-n-butyl tin coordination compound and its preparation method and application | |
| CN106220673A (en) | A kind of 2 carbonyl 2 phenylacetic acids are to toluyl hydrazone di-n-butyl tin coordination compound and its preparation method and application | |
| CN106220672A (en) | A kind of 2 carbonyl 2 phenylacetic acids are to tert-butyl benzoyl hydrazone di-n-butyl tin coordination compound and its preparation method and application | |
| CN106279260A (en) | A kind of 2 carbonyl butanoic acid salicyloyl hydrazone di-n-butyl tin coordination compounds and its preparation method and application | |
| CN106279251A (en) | A kind of 2 carbonyl propionic acid benzoyl hydrazones two are to methyl-benzyl stannum coordination compound and its preparation method and application | |
| CN106220671A (en) | A kind of 2 carbonyl 2 phenylacetic acids are to toluyl hydrazone stannous phenide coordination compound and its preparation method and application | |
| CN106317104A (en) | 2- carbonyl propionic acid p-tert-butyl benzoyl hydrazone stannous phenide complex and preparing method and application thereof | |
| CN106243148A (en) | A kind of 2 carbonyl 2 phenylacetic acid benzoyl hydrazone stannous phenide coordination compounds and its preparation method and application | |
| CN106220668A (en) | A kind of 2 carbonyl 3 phenylpropionic acid salicyloyl hydrazone di-n-butyl tin coordination compounds and its preparation method and application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |