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Porphyrin derivate with macrosubstituent, preparation process thereof and use as small molecule antioxidant

A technology of derivatives and substituents, which is applied in the fields of porphyrin derivatives with large substituents, their preparation and their application as small molecule antioxidants, which can solve the problems of limiting drug feasibility, inability to enter cells, short half-life, etc. problem, to achieve the effect of increasing practicability, treating cerebral thrombosis, and reducing toxicity

Inactive Publication Date: 2003-10-22
SINOPHARM A THINK PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the enzyme itself is a polymer with a short half-life in blood circulation, cannot enter cells, and is expensive, which limits its feasibility as a drug

Method used

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  • Porphyrin derivate with macrosubstituent, preparation process thereof and use as small molecule antioxidant

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the synthesis of iron-5,10,15,20-tetra[(N-cyclohexyl)-2'-pyridyl]porphyrin pentachloride (structural formula 1)

[0045] 10.7 g of 2-pyridylcarbaldehyde was dissolved in 1 liter of propionic acid, and then 6.7 g of pyrrole was added. The resulting mixture was heated to reflux in air for 1 hour and then cooled to room temperature. Propionic acid was distilled off under vacuum. Silica gel column separation was carried out with chloroform to obtain 1.74 g of pure 5,10,15,20-tetrakis(2'-pyridyl)porphyrin. Yield 10%.

[0046] 1 gram of 5,10,15,20-tetrakis(2'-pyridyl)porphyrin was dissolved in 10 milliliters of chlorocyclohexane and refluxed for 4 hours at 60°C. After the reaction was complete, the solution was cooled to room temperature. Distill off excess chlorocyclohexane under vacuum to obtain 1.8 grams of 5,10,15,20-tetrakis[(N-cyclohexyl)-2'-pyridyl]porphyrin tetrachloride, yield 99% .

[0047] 1.8 grams of 5,10,15,20-tetrakis[(N-cyclohexyl)-2'-pyrid...

Embodiment 2

[0048] Embodiment 2: Copper-5,10,15,20-four [(N-cyclobutanyl)-3'-pyridyl] synthesis of porphyrin tetrachloride (structural formula 2)

[0049] 10.7 g of 3-pyridylcarbaldehyde was dissolved in 1 liter of propionic acid, and then 6.7 g of pyrrole was added. The resulting mixture was heated to reflux in air for 1 hour and then cooled to room temperature. Propionic acid was distilled off under vacuum. Silica gel column separation was carried out with chloroform to obtain 2.6 g of pure 5,10,15,20-tetrakis(3'-pyridyl)porphyrin. Yield 15%.

[0050] 2 grams of 5,10,15,20-tetrakis(3'-pyridyl)porphyrin was dissolved in 30 milliliters of chlorocyclobutane and refluxed for 4 hours at 60°C. After the reaction was complete, the solution was cooled to room temperature. Distill off excess chlorocyclobutane under vacuum to obtain 3.1 g of 5,10,15,20-tetrakis[(N-cyclobutanyl)-3'-pyridyl]porphyrin tetrachloride, yield 99% .

[0051] 3 grams of 5,10,15,20-tetrakis[(N-cyclobutyl)-3'-pyridyl]...

Embodiment 3

[0052] Embodiment 3: Cobalt-5,10,15,20-four [(N-cyclobutanyl)-4'-pyridyl] synthesis of porphyrin pentachloride (structural formula 3)

[0053] 10.7 g of 4-pyridylcarbaldehyde was dissolved in 1 liter of propionic acid, and then 6.7 g of pyrrole was added. The resulting mixture was heated to reflux in air for 1 hour and then cooled to room temperature. Propionic acid was distilled off under vacuum. Silica gel column separation was carried out with chloroform to obtain 4.3 g of pure 5,10,15,20-tetrakis(4'-pyridyl)porphyrin with a yield of 25%.

[0054] 4 grams of 5,10,15,20-tetrakis(4'-pyridyl)porphyrin was dissolved in 30 milliliters of chlorocyclobutane and refluxed at 60°C for 4 hours. After the reaction was complete, the solution was cooled to room temperature. Distill off excess chlorocyclobutane under vacuum to obtain 6.1 g of 5,10,15,20-tetrakis[(N-cyclobutanyl)-4'-pyridyl]porphyrin tetrachloride, yield 99% .

[0055] 6 grams of 5,10,15,20-tetrakis[(N-cyclobutyl)-4'-...

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Abstract

The present invention discloses a porphyrin derivative with large substituent and its pharmaceutical acceptable salt and its preparation method. The described porphyrin derivative is M-5,10,15,20-tetra[(N)-substituted-n-phenyl or heterocyclic radical] porphyrin, in which n represents 2,3 and 4 postion substitution, and M is one of Fe, Mn, Co, Ni, Cu Zn, Sn, Cr and V metal ions. Said invented porphyrin derivative has higher steric hindrance, and can effectively resist the combination of porphyrin with DNA, and can reduce the mutual transformation between the different isomers, reduce toxicity of porphyrin and raise its medicinal practicability. The described porphyrin derivative can be used as small molecular antioxidant for regulating concentration of peroxide between cells of human body or in cell.

Description

technical field [0001] The invention relates to a substituted porphyrin derivative, its preparation method and its application as a small molecule antioxidant, especially a porphyrin derivative with a large substituent, its preparation method and its role as a small molecule antioxidant in regulating human body Application in terms of intercellular or intracellular peroxide concentration. Background technique [0002] Peroxide is a product of the normal physiological metabolic process of the human body. Peroxides present in human cells and between cells include O 2 -· ,OH -· , ONOO - and H 2 o 2 . Since peroxide is highly chemically reactive, it can react with the substances that make up human cells, such as cell membranes and chromosomes, thereby causing disease. [0003] Oxygen is active, can participate in important metabolic processes, and plays an important role in maintaining life. But oxygen can also cause damage to living organisms. In the body, oxygen is c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/409A61P7/02A61P9/06A61P11/00A61P25/28A61P29/00A61P31/18A61P39/06C07D487/22
Inventor 巩宪昌
Owner SINOPHARM A THINK PHARMA
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