Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Emodin azole alcohol compound and preparation method thereof

A technology for emodinazole and compound, which is applied in the field of emodinol compound and its preparation, can solve problems such as unsatisfactory anti-microbial effect, achieve strong in vitro anti-microbial activity, solve drug resistance and low cost. Effect

Active Publication Date: 2020-11-20
LINYI UNIVERSITY
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that emodin has inhibitory effects on Staphylococcus aureus, Streptococcus, Bacillus diphtheria, Bacillus subtilis, Bacillus paratyphoid, Shigella, Escherichia coli, influenza bacillus, pneumococcus, catarrhal bacteria, etc., but the antimicrobial effect is not It is too ideal. Therefore, researchers started from the parent structure of emodin for chemical modification, designed and synthesized a series of emodin derivatives with better activity, in order to develop into new antimicrobial drugs

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Emodin azole alcohol compound and preparation method thereof
  • Emodin azole alcohol compound and preparation method thereof
  • Emodin azole alcohol compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Prepare emodinazole compound I-1, the reaction formula is as follows:

[0027]

[0028] Specific steps are as follows:

[0029] Add 0.101g of 1,8-dihydroxy-3-methyl-6-(oxirane-2-ylmethoxy)anthracene-9,10-dione (shown in formula II) in the 50mL round bottom flask ), 0.053g of potassium carbonate, 0.022g of 1,2,4-triazole, and 30mL of absolute ethanol were refluxed for reaction, tracked by thin-layer chromatography until the end of the reaction, cooled to room temperature (18~25°C), and ethanol was removed by distillation under reduced pressure , the residue was purified by silica gel column chromatography using a mixture of dichloromethane and methanol at a volume ratio of 10:1 as the eluent, and dried to obtain 0.151 g of emodinazole compound I-1 as a yellow solid.

[0030] The yield of this embodiment is 64%; melting point 124-126 ℃; 1 H NMR (400MHz, DMSO-d 6 )δppm: 2.35(s,3H,CH 3 ),4.07-4.03(m,H,OCH 2 CHCH 2 ), 4.14-4.11 (m, H, OCH 2 CHCH 2 ), 4.14-4.11 (m,...

Embodiment 2

[0033] Emodin azole compound I-2, the reaction formula is as follows:

[0034]

[0035] Specific steps are as follows:

[0036] In the 50mL round bottom flask, add 0.149g of 1,8-dihydroxy-3-methyl-6-(oxirane-2-ylmethoxy)anthracene-9,10-dione (shown in formula II ), potassium carbonate 0.089g, 4-nitroimidazole 0.054g and absolute ethanol 30mL, reflux to react, thin-layer chromatography traces to the end of the reaction, cools to room temperature (18~25 ℃), removes ethanol by vacuum distillation, and the residue Purify by silica gel column chromatography using a mixture of dichloromethane and methanol at a volume ratio of 10:1 as the eluent, and dry to obtain 0.098 g of emodinazole compound I-2 as a yellow solid.

[0037] The yield of this example is 51%; melting point is 167-169°C; 1 H NMR (400MHz, DMSO-d 6 )δppm: 2.37(s,3H,CH 3 ),4.18-4.08(m,4H,OCH 2 CHCH 2 ),4.37-4.30(m,H,OCH 2 CHCH 2 ), 5.70 (s, H, OH), 6.83 (s, H, emodin-2-H), 7.10 (br, 2H, emodin-4, 5-H), 7.41 (...

Embodiment 3

[0039] Emodin azole compound I-3, the reaction formula is as follows:

[0040]

[0041] Specific steps are as follows:

[0042] In the 50mL round bottom flask, add 0.152g of 1,8-dihydroxy-3-methyl-6-(oxirane-2-ylmethoxy)anthracene-9,10-dione (shown in formula II ), potassium carbonate 0.091g, 2-methyl-5-nitroimidazole 0.061g and absolute ethanol 30mL, reflux for reaction, TLC tracking to the end of the reaction, cool to room temperature (18~25°C), and distill under reduced pressure Remove ethanol, the residue is purified by silica gel column chromatography with a mixture of dichloromethane and methanol at a volume ratio of 10:1 as an eluent, and dried to obtain 0.087g of yellow solid-like emodinazole compound I-3 .

[0043] The yield of this example is 42%; the melting point is 145-147°C; 1 H NMR (400MHz, DMSO-d 6 )δppm: 22.37(s,3H,CH 3 ),2.39(s,3H,imidazole-CH 3 ),4.21-4.10(m,5H,OCH 2 CHCH 2),5.66(br,H,OH),8.27(s,H,imidazole-4-H),8.38(s,H,imidazole-3-H),11.91(s,H,e...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the technical field of medicinal chemistry. The invention discloses an emodin azole alcohol compound as shown in a formula I which is described in the specification. The compound has relatively strong in-vitro antimicrobial activity; the compound has very high inhibitory activity on staphylococcus aureus, bacillus subtilis, micrococcus luteus, escherichia coli, proteus, pseudomonas aeruginosa, shigella dysenteriae, salmonella typhimurium and other bacteria, and candida utilis, candida albicans, saccharomyces cerevisiae, aspergillus flavus, candida albicans and other fungi. The compound can be used for preparing antibacterial and / or antifungal drugs, so that more efficient candidate drugs are provided for clinical antimicrobial treatment, and the clinical treatmentproblems of increasingly serious drug resistance, stubborn pathogenic microorganisms, newly appearing harmful microorganisms and the like are solved.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to an emodin azole alcohol compound and a preparation method thereof. Background technique [0002] Emodin, whose chemical name is 1,3,8-trihydroxy-6-methylanthraquinone, has a variety of biological activities such as immune suppression, anti-tumor, anti-microbial, antispasmodic, cough-relieving, catharsis, diuretic, etc., so in It has high clinical medical value. Studies have shown that emodin has inhibitory effects on Staphylococcus aureus, Streptococcus, Bacillus diphtheria, Bacillus subtilis, Bacillus paratyphoid, Shigella, Escherichia coli, influenza bacillus, pneumococcus, catarrhal bacteria, etc., but the antimicrobial effect is not It is too ideal. Therefore, scientific researchers started from the parent structure of emodin for chemical modification, designed and synthesized a series of emodin derivatives with better activity, in order to develop th...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/08C07D233/94A61K31/4196A61K31/4164A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07D233/94C07D249/08Y02A50/30
Inventor 张慧珍刘凤志宁志伟侯杰梁文靖杨文强
Owner LINYI UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com