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Application of Harmine derivative to preparation of antibacterial medicine

A technology of medicine and pharmacy, applied in the field of medicine, can solve the problems such as no report on the antibacterial activity of dehydrocamaprine derivatives and the like

Inactive Publication Date: 2013-05-01
XINJIANG HUASHIDAN PHARMA RES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Antibacterial activity of dehydrohalamine derivatives has not been reported in the prior art

Method used

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  • Application of Harmine derivative to preparation of antibacterial medicine
  • Application of Harmine derivative to preparation of antibacterial medicine
  • Application of Harmine derivative to preparation of antibacterial medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A-1

[0999] General synthetic process of 2-substituted β-carboline alkaloid derivatives (201-206):

[1000] β-carboline (2mmol), add an appropriate amount of ethyl acetate to dissolve it completely, add the corresponding bromine / iodoalkane (10-20mmol), heat and reflux for 8 hours, cool to room temperature, filter the precipitated solid, wash with ethyl acetate , then dissolve the solid in absolute ethanol, heat to reflux until clarification, filter while it is hot, and place it in the refrigerator for recrystallization to obtain white or light yellow crystals.

[1001] 2-Benzyl-1-methyl-β-carboline bromide (201): starting from 1-methyl-β-carboline and benzyl bromide, a light yellow crystal (0.46g, 65%) was obtained, mp >270℃; FAB-MS m / e 273; IR(KBr) 3420,1750-3250,1634,1575,1525,1500,1452,1331,1299,1258,1229,1146,740; 1H-NMR(500MHz, DMSO-d6)δ12.94(1H,s,NH);8.80-8.82(1H,d,J=7.0Hz,H-3);8.73-8.75(1H,d,J=6.5Hz,H-4) ;8.48-8.50(1H,d,J=7.5Hz,H-5);7.79-7.80(2H,m,H-8,H-7);7.25-7.47(6H,m,H...

Embodiment A-2

[1009]

[1010] A general synthetic process for the 7-position alkylation reaction (208-215):

[1011] Mix 9-ethyl-1-methyl-β-carbolin-7-ol (2.0mmol), DMF (30ml), 60% sodium hydride (0.2g, 5mmol), stir at room temperature or under ice bath for 5min, then Add the corresponding halogenated alkanes (3-5mmol), stir and react for 0.5-2 hours, TLC tracking detection (developer: acetone / petroleum ether = 1:1), after the reaction is complete, pour the reaction mixture into water, add 10M sodium hydroxide , stirred at room temperature overnight, filtered, washed with a large amount of water, dissolved the solid in absolute ethanol, adjusted the pH to 3-4 with concentrated hydrochloric acid, concentrated under reduced pressure, added water to the absolute ethanol several times, and recrystallized from acetone or acetone / ether to obtain White or light yellow solid. Dissolve the solid in a mixed solution of ethyl acetate / water, basify with saturated sodium bicarbonate solution, extract ...

Embodiment A-3

[1023]

[1024] General synthetic procedure for 7-alkoxy-9-n-butyl-1-methyl-β-carboline derivatives (216-223):

[1025] Mix 9-n-butyl-1-methyl-β-carboline-7 alcohol (2.0mmol), DMF (30ml), 60% sodium hydride (0.2g, 5mmol), stir at room temperature or under ice bath for 5min, then Add the corresponding halogenated alkanes (3.5-5mmol), stir and react for 1-2 hours, TLC tracking detection (developer: acetone / petroleum ether = 1:1), after the reaction is complete, pour the reaction mixture into water, add 10M sodium hydroxide , stirred at room temperature overnight, filtered, washed with a large amount of water, dissolved the solid in absolute ethanol, adjusted the pH to 3-4 with concentrated hydrochloric acid, concentrated under reduced pressure, added water to the absolute ethanol several times, and recrystallized from acetone or acetone / ether to obtain White or light yellow solid. Dissolve the solid in a mixed solution of ethyl acetate / water, basify with sodium bicarbonate, ...

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PUM

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Abstract

The invention discloses application of a Harmine derivative to preparation of antibacterial medicines. The bacteria is selected from Acinetobacter, Bacillus, Campylobacter, Chlamydia, Chlamydia trachomatis, Clostridium, Citrobacter, Escherichia, enterohemorrhagic escherichia coli, enteric bacteria, Enterococcus, Francisella, Haemophilus, helicobacter, Klebsiella Bacillus, Lester monocytogenes, Moraxella, Mycobacterium, Neisseria, proteus, Pseudomonas, Salmonella, shewanella oneidensis, Shigella, Stenotrophomonas, Staphylococcus, Streptococcus and Yersinia.

Description

technical field [0001] The invention relates to the application of dehydrohalamine derivatives in the preparation of antibacterial drugs, and belongs to the technical field of medicine. Background technique [0002] Harmine is a member of the β-carboline (β-carboline) alkaloid family, and its chemical name is 7-methoxy-1-methyl-9H-pyrrole[3,4-b ] indole, the molecular formula is C 13 h 12 N 2 O, molecular weight 212.25, melting point 261°C, chemical structural formula as follows: [0003] [0004] Dehydrohalamine and its analogues are widely distributed in nature. Since the first separation of dehydrohaeline compounds, people have carried out a large number of synthetic studies on dehydrohaecene compounds. According to incomplete statistics, so far, people have reported more than about 300 dehydrohaecene compounds. Alkali compounds, new dehydrohalamine compounds are still increasing. [0005] Dehydrohalpine compounds have significant antitumor activity, but also hav...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/437A61K31/444A61P31/04
CPCA61K31/437A61P31/04A61P31/10Y02A50/30
Inventor 王子厚武嘉林张淑华曹日晖马芹莫非张姝范文玺孙洁胡伏莲周凡慕春海
Owner XINJIANG HUASHIDAN PHARMA RES
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