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Synthesis method and application of antibacterial medicine tri-carbon chain methylpiperidine urolithin B and hydrochloride thereof

A technology of three-carbon chain methylpiperidine and antibacterial drugs, which is applied in the field of synthetic antibacterial drugs, can solve problems such as difficult to carry out smoothly and poor antibacterial activity tests, and achieve the effect of increasing sources

Active Publication Date: 2019-06-25
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although the antibacterial potential of urolithin has been reported in the literature, the antibacterial activity test of urolithin is very poor in water solubility, and it is difficult to carry out the antibacterial activity test smoothly. Therefore, improving the water solubility and bioavailability of urolithin has become a difficulty that researchers must break through

Method used

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  • Synthesis method and application of antibacterial medicine tri-carbon chain methylpiperidine urolithin B and hydrochloride thereof
  • Synthesis method and application of antibacterial medicine tri-carbon chain methylpiperidine urolithin B and hydrochloride thereof
  • Synthesis method and application of antibacterial medicine tri-carbon chain methylpiperidine urolithin B and hydrochloride thereof

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Experimental program
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Embodiment 1 3

[0035] The synthetic method of embodiment 1 three-carbon chain methyl piperidine urolithin B hydrochloride

[0036] (1) Synthesis of bromopropanated urolithin B (3):

[0037] Take the reactant urolithin B (2), 1,3-dibromopropane, and potassium carbonate in a molar ratio of 1:4:4, and put the total reactant (g) and acetone (ml) in a round bottom flask at a ratio of 1:2 Reflux at 60°C for 2 hours, check whether the reaction is complete by thin-layer chromatography, the inspection standard is the disappearance of light blue urolithin B fluorescent spots, after the reaction is complete, spin the acetone, pour the solid powder into a beaker and add petroleum ether, stir, and use a Buchner funnel Remove excess 1,3-dibromopropane by suction filtration, pour the obtained solid into a beaker and add water to stir, then use a Buchner funnel to suction filter to obtain a filter cake, and dry the filter cake to obtain a crude sample of bromopropanated urolithin B.

[0038] (2) Synthesis ...

Embodiment 2 3

[0053] The antibacterial application of embodiment 2 three-carbon chain methyl piperidine urolithin B hydrochloride

[0054] (1) strain

[0055] Staphylococcus aureus ATCC25923, Escherichia coli ATCC25922, Staphylococcus epidermidis AB208188, Shigella flexneri BNCC108831, Klebsiella pneumoniae RM3017, all from the School of Life Sciences, Wuhan University; Escherichia coli CMCC44102, Listeria monocytogenes Bacteria CMCC54002 and Salmonella typhimurium CMCC50115 were purchased from Beijing Putian Biotechnology Co., Ltd.

[0056] (2) Bacterial suspension preparation

[0057] Take the above-mentioned glycerol-frozen bacteria and inoculate them on the nutrient agar plate by streaking, culture at 37°C for 18h to 24h, pick a single colony and inoculate them into the nutrient broth, culture at 37°C until the logarithmic growth phase, centrifuge at 5000rpm for 6min, and collect the bacteria , washed twice with phosphate buffered saline (PBS) and then resuspended to adjust the bacter...

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Abstract

The invention provides a synthesis method and application of an antibacterial medicine, tri-carbon chain methylpiperidine urolithin B, and hydrochloride thereof. The method comprises the following steps: carrying out alkylation reaction with urolithin B serving as a parent body and 1,3-dibromopropane serving as a flexible carbon chain to obtain bromopropanized urolithin B; with methylpiperidine asa water-soluble terminal, carrying out amination reaction to the bromopropanization urolithin B to obtain the tri-carbon chain methylpiperidine urolithin B, of which the structure is shown in the specification; carrying out an acid-base salt forming reaction on the tri-carbon chain methylpiperidine urolithin B with hydrogen chloride-ethyl acetate to obtain the tri-carbon chain methylpiperidine urolithin B hydrochloride, of which the structure is shown in the specification. The compound is good in water solubility and has very good antibacterial activity on Staphylococcus aureus, Shigella flexneri, Listeria monocytogenes, Escherichia coli, Staphylococcus epidermidis and Salmonella typhimurium. The synthesis process is simple and low in cost, can be applied to industrial production, and increases the sources of existing antibacterial drugs.

Description

technical field [0001] The invention belongs to the field of synthetic antibacterial drugs, and specifically relates to a synthesis method and application of three-carbon chain methylpiperidine urolithin B and its hydrochloride. Background technique [0002] As early as the 1940s, penicillin became the first clinically used antibiotic, saving countless lives, but as time went by, bacterial resistance became stronger and stronger, and now 98% of Staphylococcus aureus are resistant to penicillin Therefore, it is imperative to obtain new antibacterial compounds. [0003] In 1932, the German chemist Dumark discovered that "Peridone" had antibacterial activity, and since then opened a milestone in medicinal chemistry represented by sulfonamides. In recent decades, countless antibacterial agents have been successfully synthesized or modified. Therefore, obtaining new antibacterial drugs through synthesis has become an indispensable means for pharmaceutical workers. [0004] Uro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A61P31/04
CPCY02A50/30
Inventor 周本宏韦平李妍兰昱
Owner WUHAN UNIV
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