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Pleuromutilin (e)-4-(1-imidazoylmethyl )cinnamic acid ester with Anti-drug resistant bacteria activity and a method of preparing the same

a technology of cinnamic acid ester and pleuromutilin, which is applied in the field of medicinal chemistry, can solve problems such as huge challenges

Active Publication Date: 2022-11-10
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a compound with anti-drug resistant bacteria activity and a method for its preparation. The compound has a specific formula (I) and can be prepared by reacting a compound of formula (II) with a compound of formula (III) or (IV). The reaction involves adding an organic solvent and a catalytic amount of triethylamine under nitrogen atmosphere to obtain a reaction mixture. The reaction mixture is then heated at a specific temperature for a specific period of time. The resulting crude product is purified and the purified compound is obtained. The invention provides a new compound that can be used to treat drug-resistant bacteria.

Problems solved by technology

Here comes a huge challenge.

Method used

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  • Pleuromutilin (e)-4-(1-imidazoylmethyl )cinnamic acid ester with Anti-drug resistant bacteria activity and a method of preparing the same
  • Pleuromutilin (e)-4-(1-imidazoylmethyl )cinnamic acid ester with Anti-drug resistant bacteria activity and a method of preparing the same
  • Pleuromutilin (e)-4-(1-imidazoylmethyl )cinnamic acid ester with Anti-drug resistant bacteria activity and a method of preparing the same

Examples

Experimental program
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example 1

Preparation of pleuromutilin (E)-4-(1-imidazoylmethyl)cinnamic acid ester (compound of formula I) ((E)-2-(((3aS,4R,5S,6S,8R,9R,9aR,12R)-5-hydroxy-4,6,9,12-tetramethyl-1-oxo-6-vinyldecahydro-3a,9-propanocyclopenta[8]annulen-8-yl)oxy)-2-oxoethyl-3-(4-((1H-imidazol-1-yl)methyl)phenyl)acrylate)

[0030]In a 100 mL three-necked flask, 246.0 mg (0.65 mmol) of pleuromutilin and 6.1 mg (0.06 mmol) of triethylamine were dissolved in 25 mL of dichloromethane under nitrogen atmosphere. 177.2 mg (0.72 mmol) of (E)-4-(1-imidazoylmethyl)cinnamic acid chloride (compound of formula III) was dissolved in 10 mL of dichloromethane, and added dropwise to the reaction mixture by a separatory funnel. After the completion of the dropwise addition, the reaction was carried out at 25° C. for 5 hours. Thin layer chromatography was used to track the reaction to completion, heating was stopped, and the protective device was removed. The reaction mixture was concentrated, washed in water, extracted with ethyl acet...

example 2

Preparation of pleuromutilin (E)-4-(1-imidazoylmethyl)cinnamic acid ester

[0032]In a 100 mL three-necked flask, 246.0 mg (0.65 mmol) of pleuromutilin and 6.1 mg (0.06 mmol) of triethylamine were dissolved in 25 mL of dichloromethane under nitrogen atmosphere. 159.9 mg (0.65 mmol) of (E)-4-(1-imidazoylmethyl)cinnamic acid chloride was dissolved in 10 mL of dichloromethane, and added dropwise to the reaction mixture by a separatory funnel. After the completion of the dropwise addition, the reaction was carried out at 25° C. for 4 hours. Thin layer chromatography was used to track the reaction to completion, heating was stopped, and the protective device was removed. The reaction mixture was concentrated, washed in water, extracted with ethyl acetate, concentrated and dried to obtain a crude product. The crude product was purified by silica gel column chromatography with dichloromethane:methanol=8:1 as eluent, and the eluent was combined and concentrated under reduced pressure to obtain...

example 3

Preparation of pleuromutilin (E)-4-(1-imidazoylmethyl)cinnamic acid ester

[0033]In a 100 mL three-necked flask, 246.0 mg (0.65 mmol) of pleuromutilin and 6.1 mg (0.06 mmol) of triethylamine were dissolved in 25 mL of dichloromethane under nitrogen atmosphere. 191.9 mg (0.78 mmol) of (E)-4-(1-imidazoylmethyl)cinnamic acid chloride was dissolved in 10 mL of dichloromethane, and added dropwise to the reaction mixture by a separatory funnel. After the completion of the dropwise addition, the reaction was carried out at 25° C. for 5 hours. Thin layer chromatography was used to track the reaction to completion, heating was stopped, and the protective device was removed. The reaction mixture was concentrated, washed in water, extracted with ethyl acetate, concentrated and dried to obtain a crude product. The crude product was purified by silica gel column chromatography with dichloromethane:methanol=10:1 as eluent, and the eluent was combined and concentrated under reduced pressure to obtai...

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Abstract

A compound with anti-drug resistant bacteria activity having the following formula (I):is disclosed. The methods of preparing the compound of formula (I) are also disclosed.

Description

FIELD OF THE INVENTION[0001]The present invention relates to the field of medicinal chemistry, and in particular, to pleuromutilin (E)-4-(1-imidazoylmethyl)cinnamic acid ester with anti-drug resistant bacteria activity and a method of preparing the same.BACKGROUND OF THE INVENTION[0002]With the widespread use of antimicrobials and the increase in various invasive operations, the spectrum of clinical infection pathogens continues to change, and the drug resistance of bacteria continues to increase. The infection rate of various drug-resistant bacteria and the mortality rate of patients have increased year by year. Here comes a huge challenge. The problem of drug-resistant bacteria has become very prominent, and solving the problem of bacterial drug resistance has become a top priority.[0003]Pleuromutilin (compound of formula II) is an antibiotic produced by submerged culture of higher fungi Pleurotus pleurotusmutilis and Pleurotus passeckeranius. It is a diterpene compound. with a mo...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/4164A61P31/04
CPCA61K31/4164A61P31/04C07D233/60
Inventor ZHAO, QIANQIANXIN, LIANGLI, JINGYIYANG, DANBIAN, RUINAZHANG, JIEZHAO, YUQINGLI, HANTIAN, BINWANG, YONGBOLIANG, CHENGYUANQI, LIANGMAO, GENNIAN
Owner SHAANXI UNIV OF SCI & TECH
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