CN106977452A - A kind of chloro-salicylic aldehyde of the cancer therapy drug 5 contracting hydrazino pyridine Schiff base nickel complex of 2 chlorine 6 and synthetic method - Google Patents
A kind of chloro-salicylic aldehyde of the cancer therapy drug 5 contracting hydrazino pyridine Schiff base nickel complex of 2 chlorine 6 and synthetic method Download PDFInfo
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- CN106977452A CN106977452A CN201710234184.1A CN201710234184A CN106977452A CN 106977452 A CN106977452 A CN 106977452A CN 201710234184 A CN201710234184 A CN 201710234184A CN 106977452 A CN106977452 A CN 106977452A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
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- 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
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Abstract
A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting 2 chlorine 6 hydrazino pyridine Schiff base nickel complex Ni (cphp)2And synthetic method.Nickel complex Ni (cphp)2Molecular formula be：C24H17Cl4N6NiO2, molecular weight is：621.95g/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 and analyze pure DMF, 0.145 0.291g analyzes pure Nickelous nitrate hexahydrate and is dissolved in 5 10mL analysis straight alcohols, it is placed in reactor, three days is stood in 80 DEG C of baking ovens, there is the green web crystal i.e. Ni of generation (cphp)2。Ni(cphp)2There is certain inhibition to JEG-3, but cis-platinum is far below to toxicity to the normal liver cells of HL 7702 strain cell, be 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 base nickel complex Ni (cphp) of 5- chloro-salicylic aldehydes contracting -2-2
(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 with certain excellent
Antitumor activity, the complex for having excellent pharmacological activity that stabilization can be formed with the metal ion in biological cell.In group
Filling and construct in terms of metal-organic framework materials has good application prospect, is a kind of novel and multifunctional in current social development
Material.
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
Nickel complex, is utilized solvent structure Ni (cphp)2。
Ni (cphp) of the present invention2Molecular formula be：C24H17Cl4N6NiO2, molecular weight is：621.95g/mol,
Hcphp is 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, 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 Ni of table one (cphp)2Crystallographic parameter
The Ni of table two (cphp)2Part bond distanceWith bond angle (°)
Table three：Complex Ni (cphp)2To the IC of 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 Ni (cphp)2Synthetic method concretely comprise 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
It is dissolved in 5-10mL and analyzes pure DMF, 0.145-0.291g analyzes pure Nickelous nitrate hexahydrate and is dissolved in 5-10mL analysis straight alcohols, is placed in
In reactor, three days are stood in 80 DEG C of baking ovens, there is the green web crystal i.e. Ni of generation (cphp)2.Surveyed by single crystal diffractometer
Determine Ni (cphp)2Structure, crystal structural data is shown in Table one, and 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 Ni of the present invention (cphp)2The structural representation of schiff base ligand used.
Fig. 2 is Ni of the present invention (cphp)2Structural representation.
Embodiment
Embodiment 1：
Ni (cphp) of the present invention2Molecular formula be：C24H17Cl4N6NiO2, molecular weight is：621.95g/mol,
Hcphp is the chloro- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-.Crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table
Two.
Ni(cphp)2Synthetic method concretely comprise 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 and analyze pure DMF, it is molten that 0.145g analyzes pure Nickelous nitrate hexahydrate
In 5mL analysis straight alcohols, it is placed in reactor, three days is stood in 80 DEG C of baking ovens, there is the i.e. Ni of green web crystal generation
(cphp)2.Yield 0.099g, yield 64%.Ni (cphp) is determined by single crystal diffractometer2Structure, crystal structural data is shown in Table
One, bond distance's bond angle data are shown in Table two.
Embodiment 2：
Ni (cphp) of the present invention2Molecular formula be：C24H17Cl4N6NiO2, molecular weight is：621.95g/mol,
Hcphp is the chloro- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-.Crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table
Two.
Ni(cphp)2Synthetic method concretely comprise 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 into 10mL to analyze in pure DMF, 0.291g analyzes pure Nickelous nitrate hexahydrate
It is dissolved in 10mL analysis straight alcohols, is placed in reactor, three days are stood in 80 DEG C of baking ovens, have red bar crystal to generate i.e. Ni
(cphp)2.Yield 0.202g, yield 65%.Ni (cphp) is determined by single crystal diffractometer2Structure, crystal structural data is shown in Table
One, bond distance's bond angle data are shown in Table two.
Claims (1)
1. a kind of chloro- 6- hydrazino pyridines Schiff base nickel complex Ni (cphp) of cancer therapy drug 5- chloro-salicylic aldehyde's contractings -2-2And synthesis side
Method, it is characterised in that Ni (cphp)2Molecular formula be：C24H17Cl4N6NiO2, molecular weight is：621.95g/mol, Hcphp is 5-
The chloro- 6- hydrazino pyridines schiff bases of chloro-salicylic aldehyde's contracting -2-.Crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two；
The Ni (cphp)2Synthetic method concretely comprise 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
5-10mL is analyzed in pure DMF, and 0.145-0.291g analyzes pure Nickelous nitrate hexahydrate and is dissolved in 5-10mL analysis straight alcohols, is placed in anti-
Answer in kettle, three days are stood in 80 DEG C of baking ovens, there is the green web crystal i.e. Ni of generation (cphp)2.Determined by single crystal diffractometer
Ni(cphp)2Structure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
The Ni of table one (cphp)2Crystallographic parameter
The Ni of table two (cphp)2Part bond distanceWith bond angle (°)
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710234184.1A CN106977452A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of the cancer therapy drug 5 contracting hydrazino pyridine Schiff base nickel complex of 2 chlorine 6 and synthetic method |
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| CN201710234184.1A CN106977452A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of the cancer therapy drug 5 contracting hydrazino pyridine Schiff base nickel complex of 2 chlorine 6 and synthetic method |
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Application publication date: 20170725 |