Water-soluble o-nitrophenol-containing copper porphyrin and Schiff base copper porphyrin complex thereof, and synthesis method and application thereof

A technology of porphyrin complexes and copper nitrophenolate, which is applied in copper organic compounds, pharmaceutical formulations, organic active ingredients, etc., and can solve problems such as limiting the application of porphyrin compounds

Active Publication Date: 2017-06-16
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 solub

Method used

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  • Water-soluble o-nitrophenol-containing copper porphyrin and Schiff base copper porphyrin complex thereof, and synthesis method and application thereof
  • Water-soluble o-nitrophenol-containing copper porphyrin and Schiff base copper porphyrin complex thereof, and synthesis method and application thereof
  • Water-soluble o-nitrophenol-containing copper porphyrin and Schiff base copper porphyrin complex thereof, and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] The synthesis of embodiment 1 water-soluble copper porphyrin (CuP-1) containing o-nitrophenol

[0054] (1) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxyl-4-hydroxyl-5-nitro)phenyl-porphyrin

[0055] Weigh 1.97g (0.01mol) of 3-methoxy-4-hydroxyl-5 nitrobenzaldehyde, dissolve it in a 250ml three-neck flask with a mixture of 150ml propionic acid and 15ml propionic anhydride, heat and stir until completely dissolved, and wait for the system After the temperature reaches 130°C, quickly add 2.7ml (0.03mol) of 4-pyridinecarbaldehyde, then slowly dropwise add 2.6ml (0.04mol) of freshly distilled pyrrole dissolved in 10ml of propionic acid, complete the addition within 10min, and react at 140°C 2h. After the reaction, distill under reduced pressure, add 20ml of the remaining solvent, add anhydrous methanol (70ml) 3.5 times the volume of the remaining solvent, and stir at room temperature for 15-25min to wash away the pyrrole polymer generated during the reaction; freeze ...

Embodiment 2

[0063] Embodiment two, the synthesis of water-soluble Schiff base copper porphyrin complex (CuP-2)

[0064] (1) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-nitro)phenyl-porphyrin: same as Example 1.

[0065] (2) Synthesis of 5,10,15-tri-(4-pyridine)-20-(3-methoxyl-4-hydroxyl-5-amino)phenyl-porphyrin

[0066] Dissolve 100mg (0.14mmol) of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-nitro)phenyl-porphyrin in 60ml (6mol / l ) hydrochloric acid, stirring to dissolve it. Under the protection of argon, 158mg (0.7mmol) of stannous chloride hydrochloric acid solution was added to the above solution, and reacted at 65°C for 18h. 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 dissolved in a sma...

Embodiment 3

[0077] Embodiment three, the synthesis of water-soluble Schiff base copper porphyrin complex (CuP-3)

[0078] (1) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-nitro)phenyl-porphyrin: same as Example 1.

[0079] (2) Synthesis of 5,10,15-tris-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-amino)phenyl-porphyrin: same as Example 2.

[0080] (3) 5,10,15-three-(4-pyridine)-20-(3-methoxy-4-hydroxyl-5-o-hydroxy m-methoxybenzimino)phenyl-porphyrin synthesis

[0081] A solution of 91mg (0.6mmol) o-vanillin in 20ml of methanol was added to a solution containing 100mg (0.15mmol) of 5,10,15-tri-(4-pyridine)-20-(3-methoxy-4- Hydroxy-5-amino)phenyl-porphyrin in 20ml DMF solution, then add 3-5 drops of glacial acetic acid dropwise, and reflux at 72°C for 48h. 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 was completed, vacuum...

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Abstract

The invention discloses water-soluble o-nitrophenol-containing copper porphyrin and a Schiff base copper porphyrin complex thereof, and a synthesis method and an application thereof, and belongs to the field of chemical application. The synthesis method of THE o-nitrophenol-containing copper porphyrin and the Schiff base complex thereof is disclosed by using functional group modification as a main means. The application of the water-soluble o-nitrophenol-containing copper porphyrin and the Schiff base copper porphyrin complex thereof in biological activity, including the interaction of calf thymus DNA (ct-DNA) and in-vitro antitumor researches, is introduced. A pyridyl cation is introduced to a porphyrin ring through modification, so the hydrophilicity of lipophilic porphyrin compounds is greatly increased; and the increase of the solubility overcomes a severe defect of the porphyrin derivatives, so the anticancer performance is significantly increased. A result of the study of the application shows that the water-soluble o-nitrophenol-containing copper porphyrin and the Schiff base complex thereof have good in-vitro antitumor activity.

Description

technical field [0001] The invention introduces a class of water-soluble copper porphyrin containing o-nitrophenol and its Schiff base copper porphyrin complex and its synthesis method; the invention also relates to this type of water-soluble copper porphyrin containing o-nitrophenol and its Schiff base The interaction between alkali-copper porphyrin complexes and calf thymus DNA (ct-DNA) and its anti-tumor application in vitro. Background technique [0002] Malignant tumor is currently the second leading cause of human death in the world, seriously threatening human health, and millions of people die of cancer every year. Therefore, the development of new and effective anticancer drugs is a very urgent and important issue in the world today. Since humans used hematoporphyrin as a fluorescent localizer in tumor surgery in the 1950s, porphyrin and its derivatives have attracted great interest from scientists. Due to their good biocompatibility, porphyrin compounds have a sp...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07F1/08A61K31/409A61K31/555A61P35/00
CPCC07D487/22C07F1/005
Inventor 哈斯其美格陈丽华肖朝虎
Owner NORTHWEST UNIVERSITY FOR NATIONALITIES
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