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

Cinnamic acid amide diazole derivatives and application thereof in antifungal drugs

A technology of cinnamic acid amidodiazoles and antifungal drugs, applied in antifungal agents, organic chemistry, etc., can solve the problems of narrow antibacterial spectrum, toxic and side effects, and interactions, and achieve good antifungal, novel structure, and good application foreground effect

Inactive Publication Date: 2020-08-14
张建蒙
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Azole antifungal drugs have been researched and developed for many years, but these drugs have exposed more and more shortcomings, such as narrow antibacterial spectrum, drug resistance, toxic and side effects, single dosage form, and drug interactions. Spectrum, high efficiency, anti-drug resistance antibacterial drugs have always been an important topic of research in this field

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
  • Cinnamic acid amide diazole derivatives and application thereof in antifungal drugs
  • Cinnamic acid amide diazole derivatives and application thereof in antifungal drugs
  • Cinnamic acid amide diazole derivatives and application thereof in antifungal drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 N-[1,3-bis(1H-imidazol-1-yl)propan-2-yl]-cinnamamide.

[0024]

[0025] Step 1 Preparation of intermediate 3.

[0026] Cinnamic acid (3.0g, 20.25mmol), EDC·HCl (4.27g, 22.27mmol) and HOBt (3.01g, 22.27mmol) were dissolved in 50mL DMF, stirred at room temperature for 1h, then serinol (2.03g, 22.27mmol) and DIEA (6.54g, 50.6mmol), stirred at room temperature for 10h, TLC monitored the reaction was complete, added 100mL of water, extracted with ethyl acetate, washed the organic layer with saturated brine, Na 2 SO 4 Let dry overnight. The desiccant was filtered off, and concentrated under reduced pressure to obtain 3.82 g of light yellow oil, with a yield of 85.27%.

[0027] LC-MS m / z[M+H] + 222.2.

[0028] Step 2 Preparation of N-[1,3-bis(1H-imidazol-1-yl)propan-2-yl]-cinnamamide.

[0029] Intermediate 3 (1.00g, 4.52mmol), CDI 1.47g (9.04mmol) and imidazole 1.23g (18.08mmol) were dissolved in 30mL acetonitrile and reacted at 70°C for 7h. TLC monitors th...

Embodiment 2

[0032] Example 2 N-[1,3-bis(1H-imidazol-1-yl)propan-2-yl]-3-(4-fluorophenyl)-acrylamide.

[0033]

[0034] LC-MS m / z[M+H] + 339.2. 1 H-NMR (400MHz, DMSO-d 6 )δ9.30(d,J=8.1Hz,1H),7.85(d,J=15.2Hz,1H),7.72(d,J=7.4Hz,2H),7.63(s,2H),7.42(d, J=7.5Hz, 2H), 7.21(s, 2H), 6.85(s, 2H), 6.35(d, J=15.2Hz, 1H), 3.94(d, J=7.1 Hz, 4H), 3.69-3.60( m, 1H).

Embodiment 3

[0035] Example 3 N-[1,3-bis(1H-imidazol-1-yl)propan-2-yl]-3-(4-chlorophenyl)-acrylamide.

[0036]

[0037] LC-MS m / z[M+H] + 356.2. 1 H-NMR (400MHz, DMSO-d 6 )δ9.31(d, J=8.2Hz, 1H), 7.85(d, J=15.2Hz, 1H), 7.70(d, J=7.5Hz, 2H), 7.63-7.60(m, 4H), 7.42( d,J=7.5Hz,2H),7.22(s,2H),6.84(s,2H),6.32(d,J=15.1Hz,1H),3.93 (d,J=7.2Hz,4H),3.68- 3.61(m,1H).

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 medicines, and particularly relates to cinnamic acid amide diazole derivatives and application thereof in antifungal treatment, in particular to application of the diazole derivatives in preparation of medicines for treating various diseases caused by fungal infection.

Description

technical field [0001] The invention belongs to the technical field of medicines, and specifically relates to cinnamic acid amide diazole derivatives and their application in antifungal, in particular to the application of diazole derivatives in the preparation of medicines for treating various diseases caused by fungal infections. Background technique [0002] Fungal infections are a class of diseases with high morbidity and mortality. Depending on the site of infection, fungal infections can be divided into superficial fungal infections and deep fungal infections. In recent years, with the increasing number of immunocompromised people such as cancer and the extensive use of immunosuppressants and broad-spectrum antibiotics, the incidence of deep fungal infections has increased year by year, seriously damaging the normal immune function of the human body. [0003] Candida, Cryptococcus, and Aspergillus are the three major pathogens that cause invasive fungal infections. C...

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
IPC IPC(8): C07D233/61C07D249/08A61P31/10
CPCC07D233/61C07D249/08A61P31/10
Inventor 张建蒙
Owner 张建蒙
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