CN107011366A - A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine schiff bases copper complex of 2 chlorine 6 and synthetic method - Google Patents
A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine schiff bases copper complex of 2 chlorine 6 and synthetic method Download PDFInfo
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- CN107011366A CN107011366A CN201710234165.9A CN201710234165A CN107011366A CN 107011366 A CN107011366 A CN 107011366A CN 201710234165 A CN201710234165 A CN 201710234165A CN 107011366 A CN107011366 A CN 107011366A
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- chloro
- cphp
- hcphp
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- schiff bases
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- 239000002262 Schiff base Substances 0.000 title claims abstract description 14
- -1 hydrazino pyridine schiff bases copper complex Chemical class 0.000 title claims abstract description 11
- 238000010189 synthetic method Methods 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims abstract description 5
- 229940079593 drug Drugs 0.000 title claims abstract description 5
- 238000011275 oncology therapy Methods 0.000 title claims abstract description 5
- 239000000460 chlorine Substances 0.000 title abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 title abstract 3
- 229910052801 chlorine Inorganic materials 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims abstract description 35
- 239000010949 copper Substances 0.000 claims abstract description 31
- 239000013078 crystal Substances 0.000 claims abstract description 17
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 7
- 238000004458 analytical method Methods 0.000 claims abstract description 7
- 150000001298 alcohols Chemical class 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 239000003643 water by type Substances 0.000 claims abstract description 5
- SXTLQDJHRPXDSB-UHFFFAOYSA-N copper;dinitrate;trihydrate Chemical compound O.O.O.[Cu+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O SXTLQDJHRPXDSB-UHFFFAOYSA-N 0.000 claims abstract description 4
- HFTSPKIAXHZROA-UHFFFAOYSA-N (6-chloropyridin-2-yl)hydrazine Chemical class NNC1=CC=CC(Cl)=N1 HFTSPKIAXHZROA-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 abstract description 8
- 239000000470 constituent Substances 0.000 abstract description 2
- 150000004699 copper complex Chemical class 0.000 abstract description 2
- 238000000034 method Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 210000005229 liver cell Anatomy 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 1
- NWELCUKYUCBVKK-UHFFFAOYSA-N pyridin-2-ylhydrazine Chemical class NNC1=CC=CC=N1 NWELCUKYUCBVKK-UHFFFAOYSA-N 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- 238000000547 structure data Methods 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- PTVDYARBVCBHSL-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu] PTVDYARBVCBHSL-UHFFFAOYSA-N 0.000 description 1
- 206010017758 gastric cancer Diseases 0.000 description 1
- 208000010749 gastric carcinoma Diseases 0.000 description 1
- 210000003494 hepatocyte Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- 239000007777 multifunctional material Substances 0.000 description 1
- 230000002611 ovarian Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 201000000498 stomach carcinoma Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- 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)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting 2 chlorine 6 hydrazino pyridine schiff bases copper complex [Cu (cphp)2]·2H2O·C2H5OH and synthetic method.The copper complex [Cu (cphp)2]·2H2O·C2H5OH molecular formula is：C24H18Cl4CuN6O2·2H2O·C2H5OH, molecular weight is：709.88g/mol, Hcphp are the 5 chloro-salicylic aldehydes contracting hydrazino pyridine schiff bases of 2 chlorine 6.By analytically pure 5 chloro-salicylic aldehydes of 1.565g, the analytically pure hydrazino pyridines of 2 chlorine 6 of 1.436g are dissolved in 30mL analysis straight alcohol solution, part Hcphp are obtained after being heated to reflux two hours.Dried 0.134 0.269g Hcphp are dissolved in 5 10mL analysis straight alcohols, 0.121 0.242g analyzes pure Gerhardite and is dissolved in 5 10mL redistilled waters, it is placed in reactor, three days is stood in 80 DEG C of baking ovens, has yellow web crystal to generate i.e. [Cu (cphp)2]·2H2O·C2H5OH。[Cu(cphp)2]·2H2O·C2H5OH has certain inhibition to JEG-3, but is far below cis-platinum to toxicity to the normal liver cells of HL 7702 strain cell, is a kind of inorganic cancer therapy drug.Present invention process is simple, with low cost, chemical constituent is easily controllable, reproducible and yield is high.
Description
Technical field
The present invention relates to a kind of chloro- 6- hydrazino pyridines schiff bases copper complexes of 5- chloro-salicylic aldehydes contracting -2- [Cu (cphp)2]·
2H2O·C2H5OH (Hcphp is the chloro- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-) and synthetic method.
Background technology
Salicylaldehyde derivatives schiff bases has stronger coordination ability, energy and metal complex, and resists with certain excellent
Tumor promotion, the complex for having excellent pharmacological activity that stabilization can be formed with the metal ion in biological cell.Assembling and
There is good application prospect in terms of constructing metal-organic framework materials, be a kind of novel and multifunctional material in current social development.
The content of the invention
The purpose of the present invention is exactly for the chloro- 6- hydrazino pyridines schiff bases of salicylaldehyde derivatives contracting -2- of design synthesizing new
Copper complex, utilizes solvent structure [Cu (cphp)2]·2H2O·C2H5OH。
[Cu (cphp) of the present invention2]·2H2O·C2H5OH molecular formula is：C24H18Cl4CuN6O2·2H2O·
C2H5OH, molecular weight is：709.88g/mol, Hcphp are the chloro- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-, with good
Bioactivity.Crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two, and the IC50 values to part cancer cell are shown in Table three.
[the Cu (cphp) of table one2]·2H2O·C2H5OH crystallographic parameter
[the Cu (cphp) of table two2]·2H2O·C2H5OH- part bond distanceWith bond angle (°)
Table three：Complex [Cu (cphp)2]·2H2O·C2H5ICs of the OH to different cell lines50Value
In table：MGC803 is gastric carcinoma cells, and HepG2 is human liver cancer cell, and NCI-H460 is human breast cancer cell, BEL-
7404 be Proliferation of Human Ovarian Cell, and HL-7702 is human normal hepatic cell strain.
[the Cu (cphp)2]·2H2O·C2H5OH synthetic method is concretely comprised the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the chloro- 6- hydrazino pyridines of the analytically pure 2- of 1.436g are dissolved in 30mL
Analyze in straight alcohol solution, part Hcphp is obtained after being heated to reflux two hours.By dried 0.134-0.269g Hcphp
5-10mL analysis straight alcohols are dissolved in, 0.121-0.242g analyzes pure Gerhardite and is dissolved in 5-10mL redistilled waters, puts
In reactor, three days are stood in 80 DEG C of baking ovens, has yellow web crystal to generate i.e. [Cu (cphp)2]·2H2O·C2H5OH。
[Cu (cphp) is determined by single crystal diffractometer2]·2H2O·C2H5OH structure, crystal structural data is shown in Table one, bond distance's bond angle
Data are shown in Table two.
The present invention has the advantages that technique is simple, with low cost, chemical constituent is easily controllable, reproducible and yield is high.
Brief description of the drawings
Fig. 1 is the present invention [Cu (cphp)2]·2H2O·C2H5The structural representation of schiff base ligand used in OH.
Fig. 2 is the present invention [Cu (cphp)2]·2H2O·C2H5OH structural representation.
Embodiment
Embodiment 1：
[Cu (cphp) of the present invention2]·2H2O·C2H5OH molecular formula is：C24H18Cl4CuN6O2·2H2O·
C2H5OH, molecular weight is：709.88g/mol, Hcphp are the chloro- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-.Crystal structure
Data are shown in Table one, and bond distance's bond angle data are shown in Table two.
[Cu(cphp)2]·2H2O·C2H5OH synthetic method is concretely comprised the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the chloro- 6- diazanyls-pyridines of the analytically pure 2- of 1.436g are dissolved in 30mL
Analyze in straight alcohol solution, part Hcphp is obtained after being heated to reflux two hours.
(2) dried 0.134g Hcphp are dissolved in 5mL analysis straight alcohols, it is molten that 0.121g analyzes pure Gerhardite
In 5mL redistilled waters, it is placed in reactor, three days is stood in 80 DEG C of baking ovens, has yellow web crystal to generate i.e. [Cu
(cphp)2]·2H2O·C2H5OH.Yield 0.115g, yield 65%.[Cu (cphp) is determined by single crystal diffractometer2]·
2H2O·C2H5OH structure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
Embodiment 2：
[Cu (cphp) of the present invention2]·2H2O·C2H5OH molecular formula is：C24H18Cl4CuN6O2·2H2O·
C2H5OH, molecular weight is：709.88g/mol, Hcphp are the chloro- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-.Crystal structure
Data are shown in Table one, and bond distance's bond angle data are shown in Table two.
[Cu(cphp)2]·2H2O·C2H5OH synthetic method is concretely comprised the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the chloro- 6- hydrazino pyridines of the analytically pure 2- of 1.436g are dissolved in 30mL
Analyze in straight alcohol solution, part Hcphp is obtained after being heated to reflux two hours.
(2) dried 0.269g Hcphp are dissolved in 10mL analysis straight alcohols, 0.291g analyzes pure three nitric hydrate
Copper is dissolved in 10mL redistilled waters, is placed in reactor, and three days are stood in 80 DEG C of baking ovens, has the generation of yellow web crystal i.e.
[Cu(cphp)2]·2H2O·C2H5OH.Yield 0.238g, yield 67%.[Cu (cphp) is determined by single crystal diffractometer2]·
2H2O·C2H5OH structure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
Claims (1)
1. a kind of chloro- 6- hydrazino pyridines schiff bases copper complexes of cancer therapy drug 5- chloro-salicylic aldehyde's contractings -2- [Cu (cphp)2]·
2H2O·C2H5OH and synthetic method, it is characterised in that [Cu (cphp)2]·2H2O·C2H5OH molecular formula is：
C24H18Cl4CuN6O2·2H2O·C2H5OH, molecular weight is：709.88g/mol, Hcphp are the chloro- 6- hydrazines of 5- chloro-salicylic aldehyde's contractings -2-
Base-pyridine schiff bases.Crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two；
[the Cu (cphp)2]·2H2O·C2H5OH synthetic method is concretely comprised the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the chloro- 6- hydrazino pyridines of the analytically pure 2- of 1.436g are dissolved in 30mL analyses
In straight alcohol solution, part Hcphp is obtained after being heated to reflux two hours.Dried 0.134-0.269g Hcphp are dissolved in
In 5-10mL analysis straight alcohols, 0.121-0.242g analyzes pure Gerhardite and is dissolved in 5-10mL redistilled waters, is placed in
In reactor, three days are stood in 80 DEG C of baking ovens, has yellow web crystal to generate i.e. [Cu (cphp)2]·2H2O·C2H5OH.It is logical
Cross single crystal diffractometer and determine [Cu (cphp)2]·2H2O·C2H5OH structure, crystal structural data is shown in Table one, bond distance's bond angle number
According to being shown in Table two.
[the Cu (cphp) of table one2]·2H2O·C2H5OH crystallographic parameter
[the Cu (cphp) of table two2]·2H2O·C2H5OH-'s09Portion1Divide bond distanceWith bond angle (°)
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| CN201710234165.9A CN107011366A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine schiff bases copper complex of 2 chlorine 6 and synthetic method |
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| CN201710234165.9A CN107011366A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine schiff bases copper complex of 2 chlorine 6 and synthetic method |
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| CN107011366A true CN107011366A (en) | 2017-08-04 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113583028A (en) * | 2021-05-31 | 2021-11-02 | 广东石油化工学院 | High-cancer-cell-selectivity anticancer drug based on metal organic complex and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103194197A (en) * | 2013-04-05 | 2013-07-10 | 桂林理工大学 | 3, 5-dibromo-salicylaldehyde-condensed 2-pyridine formhydrazide and application thereof |
| CN106432302A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | [Pr(HL1)2(NO3)3(CH3OH)2(H2O)]H2O and application to anti-cancer medicine |
| CN106432299A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Complex [Pr(L2)2(H2O)(NO3)2] and application in preparation of anti-cancer drug |
-
2017
- 2017-04-11 CN CN201710234165.9A patent/CN107011366A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103194197A (en) * | 2013-04-05 | 2013-07-10 | 桂林理工大学 | 3, 5-dibromo-salicylaldehyde-condensed 2-pyridine formhydrazide and application thereof |
| CN106432302A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | [Pr(HL1)2(NO3)3(CH3OH)2(H2O)]H2O and application to anti-cancer medicine |
| CN106432299A (en) * | 2016-09-13 | 2017-02-22 | 桂林理工大学 | Complex [Pr(L2)2(H2O)(NO3)2] and application in preparation of anti-cancer drug |
Non-Patent Citations (2)
| Title |
|---|
| DILEEP RAMAKRISHNA ET AL.: "A catalytic process for the selective oxidation of alcohols by copper(II) complexes", 《INORGANIC CHEMISTRY COMMUNICATIONS》 * |
| 袁彩霞等: "水杨醛缩芳胺席夫碱铜（II）配合物抑制蛋白酪氨酸磷酸酶活性研究", 《无机化学学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113583028A (en) * | 2021-05-31 | 2021-11-02 | 广东石油化工学院 | High-cancer-cell-selectivity anticancer drug based on metal organic complex and preparation method thereof |
| CN113583028B (en) * | 2021-05-31 | 2023-05-12 | 广东石油化工学院 | High cancer cell selectivity anticancer medicine based on metal organic complex and preparation method thereof |
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