CN107041888A - A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine schiff bases cobalt 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 bases cobalt complex of 2 bromine 6 and synthetic method Download PDFInfo
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- CN107041888A CN107041888A CN201710234170.XA CN201710234170A CN107041888A CN 107041888 A CN107041888 A CN 107041888A CN 201710234170 A CN201710234170 A CN 201710234170A CN 107041888 A CN107041888 A CN 107041888A
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
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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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Abstract
A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting 2 bromine 6 hydrazino pyridine schiff bases cobalt complex [Co (bhcp)2]2And synthetic method.The cobalt complex [Co (bhcp)2]2Molecular formula be：2(C24H16Br2Cl2CoN6O2), molecular weight is：1420.15g/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, 0.145 0.291g analyzes pure cabaltous 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 red bar crystal to generate i.e. [Co (bhcp)2]2。[Co(bhcp)2]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 bases cobalt complexes of 5- chloro-salicylic aldehydes contracting -2- [Co (bhcp)2]2And
Synthetic method (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
Cobalt complex, utilizes solvent structure [Co (bhcp)2]2。
[Co (bhcp) of the present invention2]2Molecular formula be：2(C24H16Br2Cl2CoN6O2), molecular weight is：
1420.15g/mol, Hbhcp are the bromo- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-, with good bioactivity.It is brilliant
Body structured 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 Co (bhcp) of table one2]2Crystallographic parameter
[the Co (bhcp) of table two2]2Part-2Key4It is long0 With bond angle (°)
Table three：Complex [Co (bhcp)2]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 Co (bhcp)2]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, 0.145-0.291g analyzes pure cabaltous 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 red bar crystal to generate i.e. [Co (bhcp)2]2.Pass through single crystal diffractometer
Determine [Co (bhcp)2]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 the present invention [Co (bhcp)2]2The structural representation of schiff base ligand used.
Fig. 2 is the present invention [Co (bhcp)2]2Structural representation.
Embodiment
Embodiment 1：
[Co (bhcp) of the present invention2]2Molecular formula be：2(C24H16Br2Cl2CoN6O2), molecular weight is：
1420.15g/mol, Hbhcp are the bromo- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-.Crystal structural data is shown in Table one, key
Long bond angle data are shown in Table two.
[Co(bhcp)2]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 cabaltous nitrate hexahydrate of 5mL analysis DMF, 0.145g 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 red bar crystal to generate i.e. [Co
(bhcp)2]2.Yield 0.099g, yield 56%.[Co (bhcp) is determined by single crystal diffractometer2]2Structure, crystal structure number
According to being shown in Table one, bond distance's bond angle data are shown in Table two.
Embodiment 2：
[Co (bhcp) of the present invention2]2Molecular formula be：2(C24H16Br2Cl2CoN6O2), molecular weight is：
1420.15g/mol, Hbhcp are the bromo- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-.Crystal structural data is shown in Table one, key
Long bond angle data are shown in Table two.
[Co(bhcp)2]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, 0.291g analyzes pure cabaltous 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, has the generation of red bar crystal i.e.
[Co(bhcp)2]2.Yield 0.195g, yield 55%.[Co (bhcp) is determined by single crystal diffractometer2]2Structure, crystal structure
Data are shown in Table one, and bond distance's bond angle data are shown in Table two.
Claims (1)
1. a kind of bromo- 6- hydrazino pyridines schiff bases cobalt complexes of cancer therapy drug 5- chloro-salicylic aldehyde's contractings -2- [Co (bhcp)2]2And synthesis
Method, it is characterised in that [Co (bhcp)2]2Molecular formula be：2(C24H16Br2Cl2CoN6O2), molecular weight is：1420.15g/
Mol, Hbhcp are the bromo- 6- hydrazino pyridines schiff bases of 5- chloro-salicylic aldehyde's contractings -2-.Crystal structural data is shown in Table one, bond distance's bond angle data
It is shown in Table two；
[the Co (bhcp)2]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 0.145-0.291g analyzes pure cabaltous 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 red bar crystal to generate i.e. [Co (bhcp)2]2.Surveyed by single crystal diffractometer
Fixed [Co (bhcp)2]2Structure, crystal structural data is shown in Table one, and bond distance's bond angle data are shown in Table two.
[the Co (bhcp) of table one2]2Crystallographic parameter
[the Co (bhcp) of table two2]2Part bond distanceWith bond angle (°)
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| CN201710234170.XA CN107041888A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine schiff bases cobalt complex of 2 bromine 6 and synthetic method |
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| CN201710234170.XA CN107041888A (en) | 2017-04-11 | 2017-04-11 | A kind of chloro-salicylic aldehyde of cancer therapy drug 5 contracting hydrazino pyridine schiff bases cobalt complex of 2 bromine 6 and synthetic method |
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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 |
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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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