CN107011258A - A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine Schiff base zinc complex of 2 bromine 6 and synthetic method - Google Patents
A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine Schiff base zinc complex of 2 bromine 6 and synthetic method Download PDFInfo
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- CN107011258A CN107011258A CN201710234182.2A CN201710234182A CN107011258A CN 107011258 A CN107011258 A CN 107011258A CN 201710234182 A CN201710234182 A CN 201710234182A CN 107011258 A CN107011258 A CN 107011258A
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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 bromine 6 hydrazino pyridine Schiff base zinc complex Zn (bhcp)2And synthetic method.Zn complex Zn (bhcp)2Molecular formula be：C24H16Br2Cl2N6O2Zn, molecular weight is：715.51g/mol, Hbhcp are the 5 chloro-salicylic aldehydes contracting hydrazino pyridine schiff bases of 2 bromine 6.By analytically pure 5 chloro-salicylic aldehydes of 1.565g, the analytically pure hydrazino pyridines of 2 bromine 6 of 1.880g are dissolved in 30mL analysis straight alcohol solution, part Hbhcp are obtained after being heated to reflux two hours.Dried 0.157 0.314g Hbhcp are dissolved in 5 10mL and analyze pure DMF, 0.149 0.298g analyzes pure zinc 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, has yellow web crystal to generate i.e. Zn (bhcp)2。Zn(bhcp)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 bromo- 6- hydrazino pyridines Schiff base zinc complex Zn (bhcp) of 5- chloro-salicylic aldehydes contracting -2-2
(Hbhcp is the bromo- 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 bromo- 6- hydrazino pyridines schiff bases of salicylaldehyde derivatives contracting -2- of design synthesizing new
Zn complex, is utilized solvent structure Zn (bhcp)2。
Zn (bhcp) of the present invention2Molecular formula be：C24H16Br2Cl2N6O2Zn, molecular weight is：715.51g/mol,
Hbhcp is the bromo- 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 Zn of table one (bhcp)2Crystallographic parameter
The Zn of table two (bhcp)2Part bond distanceWith bond angle (°)
Table three：Complex Zn (bhcp)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 Zn (bhcp)2Synthetic method concretely comprise the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the bromo- 6- hydrazino pyridines of the analytically pure 2- of 1.880g are dissolved in 30mL
Analyze in straight alcohol solution, part Hbhcp is obtained after being heated to reflux two hours.By dried 0.157-0.314g Hbhcp
It is dissolved in 5-10mL and analyzes pure DMF, 0.149-0.298g analyzes pure zinc 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, has yellow web crystal to generate i.e. Zn (bhcp)2.Surveyed by single crystal diffractometer
Determine Zn (bhcp)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 Zn of the present invention (bhcp)2The structural representation of schiff base ligand used.
Fig. 2 is Zn of the present invention (bhcp)2Structural representation.
Embodiment
Embodiment 1：
Zn (bhcp) of the present invention2Molecular formula be：C24H16Br2Cl2N6O2Zn, molecular weight is：715.51g/mol,
Hbhcp is the bromo- 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.
Zn(bhcp)2Synthetic method concretely comprise the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the bromo- 6- diazanyls-pyridines of the analytically pure 2- of 1.880g are dissolved in 30mL
Analyze in straight alcohol solution, part Hbhcp is obtained after being heated to reflux two hours.
(2) dried 0.157g Hbhcp are dissolved in into the pure zinc nitrate hexahydrate of 5mL analysis DMF, 0.149g analyses to be dissolved in
In 5mL analysis straight alcohols, it is placed in reactor, three days is stood in 80 DEG C of baking ovens, have yellow web crystal to generate i.e. Zn
(bhcp)2.Yield 0.098g, yield 55%.Zn (bhcp) 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：
Zn (bhcp) of the present invention2Molecular formula be：C24H16Br2Cl2N6O2Zn, molecular weight is：715.51g/mol,
Hbhcp is the bromo- 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.
Zn(bhcp)2Synthetic method concretely comprise the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the bromo- 6- hydrazino pyridines of the analytically pure 2- of 1.880g are dissolved in 30mL
Analyze in straight alcohol solution, part Hbhcp is obtained after being heated to reflux two hours.
(2) dried 0.314g Hbhcp are dissolved in into 10mL to analyze in pure DMF, 0.298g analyzes pure zinc 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 yellow web crystal to generate i.e. Zn
(bhcp)2.Yield 0.204g, yield 57%.Zn (bhcp) 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 bromo- 6- hydrazino pyridines Schiff base zinc complex Zn (bhcp) of cancer therapy drug 5- chloro-salicylic aldehyde's contractings -2-2And synthesis side
Method, it is characterised in that Zn (bhcp)2Molecular formula be：C24H16Br2Cl2N6O2Zn, molecular weight is：715.51g/mol, Hbhcp is
The bromo- 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；
The Zn (bhcp)2Synthetic method concretely comprise the following steps：
(1) by the analytically pure 5- chloro-salicylic aldehydes of 1.565g, the bromo- 6- hydrazino pyridines of the analytically pure 2- of 1.880g are dissolved in 30mL analyses
In straight alcohol solution, part Hbchp is obtained after being heated to reflux two hours.Dried 0.157-0.314g Hbhcp are dissolved in
5-10mL is analyzed in pure DMF, and 0.149-0.298g analyzes pure zinc 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 yellow web crystal to generate i.e. Zn (bhcp)2.Determined by single crystal diffractometer
Zn(bhcp)2Structure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
The Zn of table one (bhcp)2Crystallographic parameter
The Zn of table two (bhcp)2Part bond distanceWith bond angle (°)
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| CN201710234182.2A CN107011258A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine Schiff base zinc complex of 2 bromine 6 and synthetic method |
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| CN201710234182.2A CN107011258A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine Schiff base zinc complex of 2 bromine 6 and synthetic method |
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