Benzo [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof

A technology of antitumor activity and synthesis method, which is applied in the field of benzo[b][1,8]-naphthyridine-2--imine compounds and synthesis, and achieves high yield, stable product and simple synthesis process. Effect

Inactive Publication Date: 2013-05-22
YUNNAN UNIV
View PDF8 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is currently no alternative treatment for 5-fl

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 [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof
  • Benzo [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof
  • Benzo [b][1,8]-naphthyridine-2-(1H)-imide derivative with antitumor activity and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 4-p-methoxybenzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- aSynthesis of ][1,8]naphthyridine (compound 1): Add 2-chloro-3-formyl-7-methoxyquinoline (2 mmol, 0.44 g) and 2- After p-methoxybenzoylmethyleneimidazolinidine (2 mmol, 0.44 g), add 1,4-dioxane (15 mL) and piperidine (0.2 mL) and heat to 80 °C under magnetic stirring Next, react for 24 hours. The reaction was monitored by TLC. After the raw material point completely disappeared, the reaction solution was poured into 50 ml of water to quench, and a yellow flocculent solid was precipitated. After filtration, it was washed with a mixed solvent of petroleum ether / ethyl acetate = 2:1, and dried to obtain an orange solid product with a yield of 89%. Melting point: 289-290°C.

[0037] H NMR spectrum (deuterated dimethyl sulfoxide + perchloric acid, Bruker AM 500 instrument): δ = 8.74 (s, 1H, Ar H ), 8.01 (d, J =8.6 Hz, 2H, Ar H ), 7.92 (d, J =7.4 Hz, 3H, Ar H ), 7.71 (d, J =8.4 Hz,1H, Ar H ), 7.17 (d, ...

Embodiment 2

[0041] 4-p-methylbenzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a Synthesis of ][1,8]naphthyridine (compound 2): Replace 2-p-methoxybenzoylmethyleneimidazoline in Example 1 with 2-p-tolylmethylene imidazoline Pyridine can be reacted to give orange solid 4-p-methylbenzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a ][1,8]naphthyridine (Compound 2), the yield was 86%. Melting point: 278-279°C.

[0042] High resolution mass spectrometry C 23 h 20 N 3 o 2 [M+H] + , the theoretical value is 370.1550; the measured value is 370.1557.

Embodiment 3

[0044] 4-benzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a Synthesis of ][1,8]naphthyridine (compound 3): Replacing 2-p-methoxybenzoylmethyleneimidazolidinine in Example 1 with 2-benzoylmethyleneimidazolinidine for reaction 4-Benzoyl-9-methoxy-1,2-dihydrobenzo[ g ]imidazo[1,2- a ][1,8]naphthyridine (Compound 3), the yield was 84%. Melting point: 280-281°C.

[0045] High resolution mass spectrometry C 22 h 18 N 3 o 2 [M+H] + , theoretical value 356.1394; measured value, 356.1393.

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

PropertyMeasurementUnit
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Melting pointaaaaaaaaaa
Login to view more

Abstract

The invention discloses a novel benzo [b][1, 8]-naphthyridine-2-(1H)-imide derivative which has antitumor activity, and in particular relates to anti-solid tumor activity and more accurately the anti-lung cancer and anti-colon cancer activity as well as a structure shown in formula (I). The invention further discloses a synthetic method. In formula (I), n is 1, 2 or 3, but R, R1, R2, R3 and R4 are defined as in claim 1. The synthetic method comprises the step of heating a 2-halogen-3-formyl quinoline compound with a structure in formula (II) and a compound with a structure in formula (III) in an appropriate solvent in the presence of a catalyst so as to obtain a target product in formula (I).

Description

Technical field [0001] The present invention involves the activity of antitumor activity, especially the activity of antibody tumors. It is more accurate to say that it is a benzene with anti -lung cancer and anti -colorectal cancer activity [ b ] [1,8] -Piraidine-2- (1 H )--Side compounds and synthesis methods. Background technique [0002] Lung cancer is the most common malignant tumor in the lungs.The World Health Organization survey report reports that the incidence of lung cancer in many countries and regions accounted for the first place in malignant tumors and is one of the most common tumors that lead to death.And colon-rectal cancer is one of the most common malignant tumors in my country. At present, the incidence of malignant tumors is 4th.In recent years, the incidence of colorectal cancer has increased significantly, and this trend is more obvious in large and medium cities.It is also one of the most common tumors in Western countries. [0003] About 40 ~ 50%of patie...

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): C07D471/14A61K31/4745A61K31/519A61K31/551A61P35/00
Inventor 严胜骄林军张怡川
Owner YUNNAN UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap