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

Application of a 12h-indazo[2,1-a]cinnoline-12-one compound

A ketone compound and compound technology, which is applied in the application field of 12H-indazo[2,1-a]cinnoline-12-one compound, can solve the problems of limited curative effect, adverse reactions, urgent drug demand, etc. The effect of good inhibitory activity and great application prospects

Active Publication Date: 2022-05-24
ZHEJIANG UNIV OF TECH
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, specific therapeutic drugs and strategies for pancreatic cancer have not yet been developed. The pyrimidine nucleoside analog gemcitabine is still the basis of first-line chemotherapy for patients with pancreatic cancer. Its curative effect is limited and there are many adverse reactions. Urgent need

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
  • Application of a 12h-indazo[2,1-a]cinnoline-12-one compound
  • Application of a 12h-indazo[2,1-a]cinnoline-12-one compound
  • Application of a 12h-indazo[2,1-a]cinnoline-12-one compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032]

[0033] Weigh 42 mg (0.2 mmol) 2-phenylindazol-3-one, 53 mg (0.24 mmol) ethyl benzoyl diazonium, 12 mg (0.2 mmol) acetic acid and 5 mg (0.006 mmol) [Ru(p-cymene) (MeCN) 3 (SbF 6 ) 2 ] into a round-bottomed reaction flask, then 2 mL of DCE was added to dissolve, and the reaction was carried out at 60°C for 6 hours. The reaction solution was mixed with silica gel, and separated by silica gel column chromatography (eluent: petroleum ether:ethyl acetate=4:1) to obtain 72.6 mg of yellow solid with a yield of 95%.

[0034] 1 H NMR (600MHz, CDCl 3 )δ9.05(d,J=8.4Hz,1H),8.00(d,J=7.8Hz,1H),7.59(d,J=7.8Hz,1H),7.55–7.49(m,3H),7.44( d, J=7.2Hz, 2H), 7.35 (td, J=7.2, 1.2Hz, 1H), 7.21 (td, J=7.2, 1.2Hz, 1H), 7.18 (t, J=7.2Hz, 1H), 7.16–7.12 (m, 1H), 5.61 (d, J=8.4Hz, 1H), 3.94 (q, J=7.2Hz, 2H), 0.84 (t, J=7.2Hz, 3H). 13 C NMR (150MHz, CDCl 3)δ165.4,157.3,138.9,136.3,133.9,131.6,131.2,130.5,129.9,129.1,128.4,125.9,123.8,123.5,122.4,120.0,116.6,116.1,112.9,110.4,61.RMS(E)cal...

Embodiment 2

[0036]

[0037] Using 2-phenyl-5-fluoroindazol-3-one (45.6 mg, 0.2 mmol) and ethyl benzoyl diazonium (53 mg, 0.24 mmol) as raw materials, 70.4 mg was prepared according to the method of Example 1 Yellow solid (eluent: petroleum ether:ethyl acetate=4:1). Yield 88%.

[0038] 1 H NMR (600MHz, CDCl 3 )δ9.02(dd,J=8.4,1.2Hz,1H),7.64-7.58(m,2H),7.53(m,3H),7.42(m,2H),7.39-7.33(m,1H),7.23 (td, J=7.8, 1.2Hz, 1H), 6.90 (td, J=9.0, 3.0Hz, 1H), 5.56 (dd, J=9.6, 4.2Hz, 1H), 3.94 (q, J=7.2Hz, 2H), 0.84(t, J=7.2Hz, 3H). 13 C NMR (150MHz, CDCl 3 )δ165.3,158.2(d,J=242.9Hz),156.5,138.8,133.6,132.8,131.4,130.7,129.9,129.3,128.4,126.2,123.9,120.2,120.0(d,J=2.3Hz),117.4(d ,J=9.0Hz),116.3,114.7(d,J=7.8Hz),110.4,108.3(d,J=23.9Hz),61.0,13.5.HRMS(ESI)calcd for[M+H] + [C 24 H 18 FN 2 O 3 ] + 401.1296, found 401.1294.

Embodiment 3

[0040]

[0041] Using 2-phenyl-5-methoxyindazol-3-one (48.0 mg, 0.2 mmol) and ethyl benzoyl ethyl diazonium (53 mg, 0.24 mmol) as raw materials, it was prepared according to the method of Example 1. 70.1 mg of yellow solid (eluent: petroleum ether:ethyl acetate=4:1). Yield 85%.

[0042] 1 H NMR (600MHz, CDCl 3 )δ9.04(d,J=7.8Hz,1H),7.60(t,J=7.8Hz,1H),7.54(m,3H),7.42(d,J=7.8Hz,2H),7.38–7.33( m, 2H), 7.22 (t, J=7.8Hz, 1H), 6.78 (dd, J=9.6, 3.0Hz, 1H), 5.50 (d, J=9.6Hz, 1H), 3.93 (q, J=7.2 Hz, 2H), 3.83(s, 3H), 0.83(t, J=7.2Hz, 3H). 13 C NMR (150MHz, CDCl 3 )δ165.5,157.1,155.7,139.4,133.6,131.8,131.3,130.5,129.9,129.2,128.2,125.9,123.8,122.3,120.3,117.3,116.3,114.4,109.3,102.8,60.9RMS(ESI )calcd for[M+H] + [C 25 H 21 N 2 O 4 ] + 413.1496, found 413.1501.

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 the application of a 12H-indazol[2,1-a]cinnoline-12-ketone compound, the 12H-indazol[2,1-a]cinnoline-12-ketone compound The application of the pharmaceutically acceptable salt or hydrate thereof in the preparation of a medicine for treating malignant tumors. The compound has good inhibitory activity especially on human prostate cancer PC-3 cells and human pancreatic cancer PANC-1 cells, and can inhibit their proliferation in a dose-dependent manner, and has great application prospects.

Description

technical field [0001] The present invention relates to the application of a class of 12H-indazo[2,1-a]cinnoline-12-one compounds or their pharmaceutically acceptable salts or hydrates in the preparation of antitumor drugs. Background technique [0002] Cancer is one of the major diseases that seriously affects human health and threatens human life. The World Health Organization (WHO) and national government health authorities have made the fight against cancer a top priority. [0003] Prostate cancer is one of the common male malignant tumors. There were 161,360 new prostate cancer cases in the United States in 2017, accounting for the first (19%) incidence of male malignant tumors; 26,730 new prostate cancer deaths, accounting for the third male malignant tumor mortality (8%). In 2015, there were 60,300 new cases of prostate cancer in my country, and the incidence of prostate cancer increased by 10% every year. Currently, prostate cancer treatment is based on chemothera...

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): A61K31/5025A61K31/5377A61K31/675A61P35/00
CPCA61K31/5025A61K31/5377A61K31/675A61P35/00
Inventor 侯卫白芮松阮奔放
Owner ZHEJIANG UNIV OF TECH
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