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Water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof, as well as synthesis methods and application of water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof

A technology of a porphyrin complex and a synthesis method, applied to the application of water-soluble nitro-containing copper porphyrin in anti-tumor in vitro, a new water-soluble nitro-containing copper porphyrin and a water-soluble Schiff alkali copper porphyrin complex It can solve problems such as limiting the application of porphyrin compounds

Inactive Publication Date: 2018-05-04
NORTHWEST UNIVERSITY FOR NATIONALITIES
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But at the same time, due to the large rigid spatial configuration of porphyrin compounds, their solubility in water is almost zero, which greatly limits the application of porphyrin compounds in medicine.

Method used

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  • Water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof, as well as synthesis methods and application of water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof
  • Water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof, as well as synthesis methods and application of water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof
  • Water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof, as well as synthesis methods and application of water-soluble nitryl-containing copper porphyrin and water-soluble Schiff base copper porphyrin complex thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment one, the synthesis of water-soluble nitro-containing copper porphyrin (Cu-Por-1)

[0057] (1) Synthesis of 5,10,15-tri-(4-pyridine)-20-(4-p-nitro)phenyl-porphyrin

[0058] Weigh 1.51g (0.01mol) of p-nitrobenzaldehyde into a 250mL three-necked flask, add a mixed solution of 180mL propionic acid and 15mL propionic anhydride, heat and stir to 130°C, quickly add 2.7mL (0.03mol) 4-pyridinecarbaldehyde, Then slowly add 2.6 mL (0.04 mol) of freshly distilled pyrrole dissolved in 10 mL of propionic acid dropwise with a dropping funnel, complete the addition within 10 min, and reflux at 140°C for 2.5 h. After the reaction, distill under reduced pressure to remove 175mL of solvent and 20ml of remaining solvent, add anhydrous methanol (90ml) 4.5 times the volume of remaining solvent, and stir at room temperature for 0.5h to wash away the pyrrole polymer generated during the reaction. Freeze (-18°C) overnight, and a purple precipitate precipitated out, which was filtere...

Embodiment 2

[0069] Embodiment two, the synthesis of water-soluble Schiff base copper porphyrin complex (Cu-Por-2)

[0070] (1) Synthesis of 5,10,15-three-(4-pyridine)-20-(4-p-nitro)phenyl-porphyrin:

[0071] Same as embodiment one.

[0072] (2) Synthesis of 5,10,15-tri-(4-pyridine)-20-(4-p-amino)phenyl-porphyrin

[0073]Weigh 100mg (0.15mmol) of 5,10,15-tris-(4-pyridine)-20-(4-p-nitro)phenyl-porphyrin in a 100mL three-necked round-bottomed flask, add 60mL (6mol / l) Hydrochloric acid, stir to dissolve. Under the protection of argon, 203 mg (0.9 mmol) of stannous chloride in hydrochloric acid solution was added to the above solution, and reacted at room temperature for 24 hours. After the reaction, neutralize and filter with 5mol / l sodium hydroxide solution, collect the filter cake, dissolve in the mixed solution (V / V=1 / 5) of methanol and dichloromethane, extract with water several times, and collect the organic phase , spin-dried to obtain a purple crude product. The crude product was ...

Embodiment 3

[0088] Embodiment three, the synthesis of water-soluble Schiff base copper porphyrin complex (Cu-Por-3)

[0089] (1) Synthesis of 5,10,15-tris-(4-pyridine)-20-(4-p-nitro)phenyl-porphyrin: same as Example 1.

[0090] (2) Synthesis of 5,10,15-tris-(4-pyridine)-20-(4-p-amino)phenyl-porphyrin: same as Example 2.

[0091] (3) Synthesis of 5,10,15-tri-(4-pyridine)-20-(4-o-hydroxy-m-methoxybenzimino)phenyl-porphyrin

[0092] 100mg (0.15mmol) of 5,10,15-tris-(4-pyridine)-20-(4-p-amino)phenyl-porphyrin was dissolved in 30mL of chloroform, and 115mg (0.75 mmol) o-vanillin in 30mL of methanol solution, then dropwise added 3-5 drops of glacial acetic acid, and refluxed at 72°C for 36h. Glacial acetic acid addition is 0.06~0.1 times of 5,10,15-three-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-amino)phenyl-porphyrin molar weight, ice Acetic acid acts as a catalyst. After the reaction is completed, vacuum rotary steaming leaves 5 mL of solvent remaining, then dropwise add petroleum ether unt...

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Abstract

The invention dislcoses synthesis methods and bioactive application of nitryl-containing copper porphyrin and a Schiff base copper complex thereof, and belongs to the field of chemical application. Firstly the synthesis methods of the nitryl-containing copper porphyrin and the Schiff base copper complex thereof are introduced by taking functional group modification as a main means; secondly the bioactive application is introduced, including research on mutual action of the nitryl-containing copper porphyrin and calf thymus DNA (CT-DNA) and in-vitro tumor resisting. Moreover, pyridyl cation isintroduced onto a porphyrin ring by means of modification, hydrophilicity of an oleophilic porphyrin compound is greatly increased, the increasement of solubility overcomes a great defect of a porphyrin derivative, so that the cancer resistance of the porphyrin derivative is remarkably improved. Through the research on mutual action of the nitryl-containing copper porphyrin and the calf thymus DNAand in-vitro tumor resisting, it is preliminarily considered that the synthesized novel water-soluble nitryl-containing copper porphyrin and the Schiff base copper complex thereof have better in-vitro anti-tumor activity.

Description

technical field [0001] The invention provides a class of novel water-soluble nitro-copper porphyrins and their water-soluble Schiff base copper porphyrin complexes, as well as their synthesis method; the invention also relates to such water-soluble nitro-copper porphyrins and their water-soluble The invention relates to the interaction between Schiff base copper porphyrin complex and calf thymus DNA (CT-DNA) and the application of water-soluble nitro-containing copper porphyrin in anti-tumor in vitro; it belongs to the field of chemical application. Background technique [0002] The research on the interaction of large conjugated molecular porphyrin compounds with four pyrrole rings and four methine bridges, and DNA has become an important topic in medical research. Studies have shown that the key to designing and synthesizing anti-tumor drug molecules with high activity and low toxic and side effects is to study the interaction between drug molecules and DNA. , Structure o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C07F1/08A61K31/555A61P35/00
CPCC07D487/22C07F1/005
Inventor 哈斯其美格肖朝虎程燕魏玉梅
Owner NORTHWEST UNIVERSITY FOR NATIONALITIES
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