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Porphyrin derivative and application for the same as small molecule antioxidant

A derivative, porphyrin technology, applied in a class of porphyrin derivatives and its application as a small molecule antioxidant, can solve the problems of limiting drug feasibility, high cost, and inability to enter cells

Inactive Publication Date: 2008-08-06
JINAN SAIWEN PHARMTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 derivative and application for the same as small molecule antioxidant
  • Porphyrin derivative and application for the same as small molecule antioxidant
  • Porphyrin derivative and application for the same as small molecule antioxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the preparation of 3-(2-methoxyethoxy) benzaldehyde

[0034]

[0035] Dissolve 100 grams of m-hydroxybenzaldehyde in 1 liter of DMF, add 226 grams of anhydrous potassium carbonate, stir for 30 minutes, add 81.3 grams of 2-chloroethyl methyl ether, heat and reflux for 6 hours, evaporate DMF under reduced pressure, add Dissolve in 500 ml of water, filter, extract the filtrate 3 times with dichloromethane, combine the extracts, wash with 200 ml of 2% sodium hydroxide solution, wash with water 3 times, dry over anhydrous sodium sulfate, filter, evaporate the solvent, 154 g of product were obtained. ESI-MS: [M+H] + , 181; 1 H NMR (DMSO-d 6 ): δ3.31(s, 3H), 3.67(t, J=4.56Hz, 2H), 4.17(t, J=4.56Hz, 2H), 7.30(m, 1H), 7.43(m, 1H), 7.51 (m, 2H), 9.97(s, 1H).

Embodiment 2

[0036] Embodiment 2: the preparation of methoxyethyl p-toluenesulfonate

[0037]

[0038] Cool the mixture of 38 grams of ethylene glycol monomethyl ether and 120 grams of anhydrous pyridine to -6°C in an ice bath, add 101 grams of p-toluenesulfonyl chloride in batches, control the temperature not to exceed 0°C, and continue stirring for 30 minutes after the addition , remove the ice bath, and react at room temperature for 4 hours. The reaction mixture was slowly poured into a mixture of 250 ml of hydrochloric acid and 700 g of ice, stirred for 20 minutes, extracted 3 times with ethyl acetate, combined extracts, washed with water 3 times, dried over anhydrous sodium sulfate, and distilled off ethyl acetate to obtain 84 grams of product.

Embodiment 3

[0039] Embodiment 3: the preparation of 3-(2-methoxyethoxy) benzaldehyde

[0040]

[0041] Dissolve 12 grams of m-hydroxybenzaldehyde in 150 milliliters of DMF, add 27.6 grams of anhydrous potassium carbonate, stir, add 23 grams of methoxyethyl p-toluenesulfonate, heat and reflux for 3 hours, and evaporate DMF under reduced pressure , add 200 milliliters of water to dissolve, extract 3 times with dichloromethane, combine the extracts, wash with 200 milliliters of 5% sodium hydroxide solution, wash with water 3 times, dry over anhydrous sodium sulfate, filter, and distill off the solvent to obtain 16 grams of product.

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PUM

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Abstract

The invention discloses a porphyrin derivative and pharmacy acceptable salt and a relative preparation method, wherein the porphyrin derivative is M-5, 10, 15, 20-4[3-polyalcohol ether] porphyrin, M is Fe, Mn, Co, Ni, Cu, Zn, Sn, Cr, V or Pt. The porphyrin derivative can be used as small molecular antioxidant to adjust the density of hyperoxide between human cells or in human cells, to protect human body from peroxy radical and other hyperoxides derived from peroxy radical, to prevent and treat the diseases caused by harmful hyperoxide.

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, its preparation method and its use as a small molecule antioxidant in regulating intercellular or intracellular peroxidation of human body applications in 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 converted into a variety of ...

Claims

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Application Information

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IPC IPC(8): C07D487/22A61K31/409A61P39/06
CPCA61P3/10A61P7/02A61P17/18A61P19/02A61P25/16A61P31/18A61P35/00A61P39/06C07D487/22
Inventor 巩宪昌胡泰友东长志郭天顺宋彩燕邓知平
Owner JINAN SAIWEN PHARMTECH
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