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Pyrrole-2-aldehyde compound as well as preparation method and application thereof

An aldehyde compound and pyrrole technology, applied in the field of pharmacy, can solve the problems such as no reports on the activity of monomer components, and achieve the effects of low toxicity, increased benefit, and simple preparation process

Pending Publication Date: 2022-06-24
XIANGYA HOSPITAL CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned pharmacological activities are all researches on the water extract or ethanol extract of Moringa oleifera seed, and there is no report on the activity of the monomer components

Method used

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  • Pyrrole-2-aldehyde compound as well as preparation method and application thereof
  • Pyrrole-2-aldehyde compound as well as preparation method and application thereof
  • Pyrrole-2-aldehyde compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Extraction, Separation and Structure Identification of Pyrrole-2-aldehyde Compounds

[0103] Take 10 kg of Moringa oleifera seeds and grind them, add 8 times the weight of purified water for ultrasonic extraction three times, each time for 1 hour, combine the extracts, concentrate, filter, and adsorb the filtrate on a PHD-300 macroporous resin column, wash with water, 50% ethanol and 90% ethanol in sequence The water, 50% ethanol and 90% ethanol eluents were collected respectively, and concentrated to obtain fluid extracts of three eluted parts. Among them, about 1.0kg of the water-washed liquid extract was applied to MCI resin, and then eluted with water, 50% ethanol and 90% ethanol in sequence, and the eluents of water, 50% ethanol and 90% ethanol were collected respectively, and the eluent was collected, concentrated, and decompressed. Dry to obtain the extract of the three eluted parts of the MCI column. Wherein MCI50% ethanol eluted extract 104g, put on the revers...

Embodiment 2

[0142] Synthesis of Pyrrole-2-aldehyde Compounds

[0143] First take KOH, pyrrole-2-aldehyde components, and benzyl chloride with a molar ratio of 1:1:1, add 5 mL of DMSO, heat and stir in an oil bath at 65°C for 24 hours, mix the sample with silica gel after the reaction is completed, and separate it with a silica gel column. : 1 petroleum ether: ethyl acetate eluted, collected the fractions, plated and combined, purified to obtain the reaction product, the yield was 60%-80%, and synthesized to obtain the product XYHC-1, XYHC-2. The general reaction formula is as follows:

[0144]

[0145] Among them, R 2 is hydrogen, methyl, hydroxymethyl, aliphatic ether group, nitrogen-containing heterocycle, sulfur-containing heterocycle, halogenated benzene ring or halogenated benzyl; R 3 is hydrogen, methyl, ethyl, benzene ring, benzyl, halogenated benzene ring, halogenated benzyl, N-containing heterocycle or sulfur-containing heterocycle. After identification, the structure of th...

Embodiment 3

[0153] Effects of pyrrole-2-aldehyde compounds on the scavenging rate of oxidative stress free radicals

[0154] 1. DPPH (1,1-Diphenyl-2-picrylhydrazyl radical) is 1,1-diphenyl-2-picrylhydrazyl radical. In the molecule, due to the presence of multiple electron-withdrawing -NO 2 And the large π bond of the benzene ring, so the nitrogen radical can exist stably. When DPPH free radicals are removed, the absorbance A value at the maximum absorption wavelength of 519nm decreases accordingly.

[0155] Preparation and handling of DPPH solvent

[0156] Preparation of DPPH test solution: Dissolve 1 mg of DPPH in about 20 mL of solvent (ethanol, 95% ethanol or methanol), ultrasonicate for 5 minutes, and shake fully to make the upper and lower parts uniform. Take 1mL DPPH solution, measure A value at 519nm, and make A=1.2-1.3 the best. The DPPH solution is best kept away from light and used up within 3.5 hours.

[0157] Determination of experimental samples

[0158] The pyrrole-2-a...

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Abstract

The invention relates to a pyrrole-2-aldehyde compound and a derivative thereof. The structural general formula of the compound is shown as (I), wherein R1 is glycosyl benzyl, substituted glycosyl benzyl, C1-C10 alkyl, C1-C10 substituted alkyl, C1-C12 aryl, C1-C12 substituted aryl, C1-C6 fatty alcohol or ester formed by C1-C6 fatty alcohol and C1-C6 carboxylic acid, C1-C6 carboxylic acid or ester formed by C1-C6 carboxylic acid and C1-C6 fatty alcohol, C1-C10 oxygen-containing alkyl, C1-C10 substituted oxygen-containing alkyl, nitrogen-containing heterocyclic ring or sulfur-containing heterocyclic ring; the invention also relates to application of the compound in neuroprotection and health food. Experiments show that the compound disclosed by the invention has a remarkable effect of resisting oxidative damage. The compound disclosed by the invention has the characteristics of clear active mechanism, low toxicity, safety and the like, and has a wide application prospect.

Description

technical field [0001] The invention belongs to the field of pharmacy, and specifically relates to pyrrole-2-aldehyde compounds, their preparation method and application. Background technique [0002] Moringa (Moringa oleifera Lam.) is a plant of the genus Moringa in the Moringaceae family, native to tropical and subtropical regions such as India and Africa (Guo Liqun et al. Tropical Agricultural Science, 2015, 35(6): 11-17; Ren Guangxu et al. . Food Research and Development, 2016, 37(16): 219-222). After the 1960s, it was planted on a large scale in Yunnan, Hainan, Guangdong, Guangxi and other places in China (Dong Xiaoying, et al. Guangdong Feed, 2008, 17(9): 39-41). The roots, stems, leaves, flowers and seeds of Moringa oleifera are all medicinal (Flora of China, 1984:34(1):6). Moringa seed is the seed of Moringa oleifera, and its main chemical components are phenols, alkaloids, amides, flavonoids, polysaccharides, etc. Modern pharmacological studies have shown that Mo...

Claims

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Application Information

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IPC IPC(8): C07D207/333C07H15/26A61K31/40A61K31/7056A61P39/06A61P25/00A61P9/10A23L33/105
CPCC07D207/333C07H15/26A61P39/06A61P25/00A61P9/10A23L33/105A23V2002/00A23V2200/322A23V2200/326A23V2300/14A23V2300/38
Inventor 蒋跃平刘韶雷光华贺佳刘蓉
Owner XIANGYA HOSPITAL CENT SOUTH UNIV
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