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

Benzo[c]benzopyrone derivatives and their applications

A technology of benzopyrone and benzopyran, applied in the field of benzo[c]benzopyrone derivatives and their application in the treatment of cancer diseases

Active Publication Date: 2022-04-15
WUHAN UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research on urolithin skeleton derivatives in the field of anti-cancer has not yet been seen.

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
  • Benzo[c]benzopyrone derivatives and their applications
  • Benzo[c]benzopyrone derivatives and their applications
  • Benzo[c]benzopyrone derivatives and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] The features and advantages of the present invention can be further understood through the following detailed description in conjunction with the accompanying drawings. The examples provided are only illustrative of the method of the present invention and do not limit the rest of the present disclosure in any way. [Example 1] Preparation of 3-(3-(4-methylpiperazin-1-yl)-propyl)-6H-benzo[c]benzopyran-6-one (BH1901)

[0036] Reaction 1

[0037]

[0038] 1) Synthesis of intermediates: Weigh urolithin B (20.2g), 1,3-dibromopropane (40.4g) and potassium carbonate (27.6g) in sequence in a 500mL round bottom flask, using acetone (200mL) as solvent , 50 ° C heating reaction 2h. Thin-layer chromatography (TLC) monitors, and the reaction can be stopped after the light blue raw material fluorescent spots disappear. Spin dry the system, dissolve the solid powder with petroleum ether, and spin dry again. Using silica gel as the stationary phase, it was eluted with petroleum e...

Embodiment 2

[0042] [Example 2] Preparation of 3-(3-morpholin-1-yl)-propyl)-6H-benzo[c]benzopyran-6-one (BH1902)

[0043] Replace 4-methylpiperazine with morpholine, and prepare the target compound according to the method of Example 1. White crystals were obtained. Such as figure 2 shown. 1H NMR (400MHz, DMSO-d6) δ8.29(d, J=8.1Hz, 1H, Ar-H), 8.25~8.15(m, 2H, Ar-H), 7.89(t, J=7.6Hz, 1H ,Ar-H),7.58(t,J=7.5Hz,1H,Ar-H),6.97(dd,J=4.5,2.2Hz,2H,Ar-H),4.10(t,J=6.3Hz,2H , O-CH2), 3.57(t, J=4.4Hz, 4H, -CH2-O-CH2), 2.41(dd, J=18.6, 11.4Hz, 6H, N-CH2), 1.90(p, J=6.6 Hz, 2H, -CH2)., Anal. Calcd for C20H21O4N, ESI-MS: 339.38 [M+H]+.

Embodiment 3

[0044] [Example 3] Preparation of 3-(3-(4-methylpiperidin-1-yl)-propyl)-6H-benzo[c]benzopyran-6-one (BH1903)

[0045] Replace 4-methylpiperazine with 4-methylpiperidine, and prepare the target compound according to the method of Example 1. Yellow crystals were obtained. Such as image 3 shown. 1H NMR (400MHz, DMSO-d6) δ8.17~8.27(m, 3H, Ar-H), 7.87(t, J=7.5Hz, 1H, Ar-H), 7.56(t, J=7.5Hz, 1H ,Ar-H),6.93(d,J=6.8Hz,2H,Ar-H),4.06(t,J=5.8Hz,2H,-O-CH2-),2.81(d,J=10.9Hz,2H ), 2.39(t, J=6.9Hz, 2H, -CH2-), 1.84(t, J=9.6Hz, 4H, -CH2-), 1.54(d, J=12.0Hz, 2H, -CH2-), 1.27(s,1H,-CH-),1.11(dd,J=22.1,10.6Hz,2H,-CH2-),0.85(d,J=6.2Hz,3H,-CH3), Anal.Calcd for C22H25O3N, ESI-MS: 351.44 [M+H]+.

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 discloses a benzo[c]benzopyrone derivative and application thereof. Through 1,3-dibromopropane bridge chain, different N-terminal end groups are introduced into urolithin derivatives, and a series of Uro B skeleton-containing (benzo[c]benzene) as shown in formula (I) are designed and synthesized chemical derivatives of pyrone). It can be applied to prepare various antitumor drugs, and is especially suitable for bladder cancer.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a benzo[c]benzopyrone derivative and its application in treating cancer diseases. Background technique [0002] Bladder cancer is the most common malignant tumor of the urinary system. The biological behavior of bladder tumors is complex and changeable, and they are prone to recurrence, invasion and metastasis. In addition to surgery, systemic chemotherapy has become the standard treatment for metastatic bladder cancer. Chemotherapeutic drugs commonly used in the treatment of bladder cancer include doxorubicin, hydroxycamptothecin, mitomycin, etc. However, due to the widespread emergence of drug resistance, bladder cancer cells are becoming less and less sensitive to these drugs. App doesn't work well. Therefore, the development of new anti-bladder cancer drugs is becoming more and more urgent. It is one of the hot spots in medical research to find low-toxicity an...

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 Patents(China)
IPC IPC(8): C07D311/80C07D405/12A61K31/496A61K31/5377A61K31/453A61K31/4025A61P35/00
CPCC07D311/80C07D405/12A61P35/00
Inventor 周本宏李妍韦平兰昱
Owner WUHAN UNIV
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