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

Heteroannelated anthraquinone derivatives and the synthesis method thereof

a technology of heterocyclic compound and anthraquinone, which is applied in the field of heterocyclic compound active ingredients, drug compositions, etc., can solve the problems of poor production rate, and achieve the effect of facilitating the study and application of cancer cells and inhibiting the proliferation activity of cancer cells

Inactive Publication Date: 2009-10-08
NAT DEFENSE MEDICAL CENT
View PDF0 Cites 8 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

"The present invention provides a series of heteroannelated anthraquinone derivatives that can inhibit the growth of cancer cells and the proliferation of cell populations. These compounds have specific structures that make them effective in inhibiting cancer cell growth and can be used in pharmaceutical compositions for treating cancer. The invention also provides methods for synthesizing these compounds and their use in treating cancer."

Problems solved by technology

However, this method only discloses the substituent of aromatic groups, and has a poor production rate (Peng et al., J. Org. Chem. 2005, 70, 10524-31).

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
  • Heteroannelated anthraquinone derivatives and the synthesis method thereof
  • Heteroannelated anthraquinone derivatives and the synthesis method thereof
  • Heteroannelated anthraquinone derivatives and the synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

embodiment 1 (

2-Methyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 2)

[0030]1,2-Diaminoanthraquinone (1.19 g, 5 mmol) is dissolved in 30 mL of N,N-dimethylformamide, and chloroacetyl chloride (0.5 mL, 6 mmol) is added thereinto. After ten hours of mixing and reacting by a reverse flow, the mixture is transferred into 200 mL of icy water. After filtering, the precipitate is collected and washed by hot alcohol, so as to obtain the black compound No. 2.

[0031]The compound No. 2 has the following characterstics: MW 262.0724 (C16H9N2O2); Rf: 0.79 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 1667 (CO); EI-MS m / z: 262 (M+, 100%); 1H-NMR (300 MHz, DMSO-d6) d (ppm): 2.72 (3H, s,—CH3), 7.75-7.82 (2H, m, Ar—H7,10), 7.93 (1H, d, J=8.4 Hz, Ar—H5), 8.13 (1H, d, J=8.4 Hz, Ar—H4), 8.19-8.23 (1H, m, Ar—H8,9), 11.01 (1H, br, —NH); and 13C-NMR (75 MHz, DMSO-d6) d (ppm): 23.89, 120.23, 121.22, 125.29, 126.19, 126.75, 127.19, 128.17, 128.87, 132.98, 134.18, 134.42, 148.22, 158.09, 182.43 (CO), 185.13 (CO).

embodiment 2 (

2-Chloroacetyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 3)

[0032]

[0033]Except controlling the reacting temperature in 50-60° C., all steps are identical with the steps for manufacturing the compound No. 2, and the yellowish brown compound No. 3 can be obtained.

[0034]The compound No. 3 has the following characterstics: MW 296.0353 (C16H9N2O2Cl); Rf: 0.5 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 3359(NH), 1660 (CO); HRMS (ESI-TOF) m / z: calcd for C16H10N2O2Cl+ [M+H]+: 297.0425, found: 297.0426; 1H-NMR (300 MHz, CDCl3) d (ppm): 4.92 (2H, s, —CH2Cl), 7.80-7.83 (2H, m, Ar—H7,10), 8.08 (1H, d, J=8.4 Hz, Ar—H5), 8.24(1H, d, J=8.4 Hz, Ar—H4), d8.26-8.35(2H, m, Ar—H8,9), d11.21(1H, br, —NH); and 13C-NMR (75 MHz, DMSO) d (ppm): 37.80, 119.35, 121.27, 125.95, 126.83, 127.40, 129.06, 132.35, 133.47, 133.64, 134.88, 135.10, 148.89, 156.93, 183.04 (CO), 183.83 (CO).

embodiment 3 (

2-Ethyl-1(3)H-anthra[1,2-d]imidazole-6,11-dione, No. 4)

[0035]

[0036]1,2-Diaminoanthraquinone (1.19 g, 5 mmol) was dissolved in dimethylformamide (30 mL), and propionaldehyde (0.29 g, 5 mmol) is added thereinto. Concentrated sulfuric acid (0.1 mL) is added thereinto for catalyzation. After mixing and reacting at room temperature for one hour, the reacted mixture is transferred into 200 mL of icy water and is extracted by using dichloromethane. The extract is dried, and crystallized by using alcholo, so as to obtain the brown compound No. 4.

[0037]The compound No. 4 has the following characterstics: MW 276.0899 (C17H12N2O2); Rf: 0.75 (ethyl acetate: dichloromethane=1:4); IR (KBr) cm−1: 1669 (CO); HRMS (ESI-TOF) m / z: calcd for C17H13N2O2+ [M+H]+: 277.0971, found: 277.0975 calcd for C17H12N2O2Na+ [M+Na]+: 299.0971, found: 299.0794; 1H-NMR (300 MHz, CDCl3) d (ppm): 1.51 (3H, t, J=7.5 Hz, —CH3), 3.05 (2H, q, J=7.5 Hz, —CH2—), 7.73-7.81 (2H, m, Ar—H7,10), 7.99 (1H, d, J=8.4 Hz, Ar—H5), d8.16...

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
temperatureaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

A heteroannelated anthraquinone derivative compound is provided. The heteroannelated anthraquinone derivative compound is represented by a formula (I):wherein R1 is a substituent being one selected from a group consisting of i) a first substituent being one selected from a group consisting of a hydryl group, an amino group, a nitro group, a hydroxyl group and a cyan group, ii) a second substituent being one selected from a group consisting of (CH2)nX, a straight (CH2)n alkyl group, a (CH2)n alkoxyl group, a branched (CH2)n alkyl group, a C3˜C12nephthenic group, and a C3˜C12 cyclic alkoxyl group, wherein 1=n=12, and X is a halogen, iii) a third substituent being one selected from a group consisting of a straight C1˜C8 alkyl group with a double-bond, a C1˜C8 alkoxyl group with a double-bond, a branched C1˜C8 alkyl group with a double-bond and a C3˜C8 nephthenic group with a double-bond, and iv) a fourth substituent of a C5˜C12 heterocyclic group.

Description

FIELD OF THE INVENTION[0001]The present invention relates to heteroannelated anthraquinone derivatives for inhibiting a proliferation activity of a cancer cell, and more particularly to a series of heteroannelated anthraquinone derivatives and the synthesis method thereof.BACKGROUND OF THE INVENTION[0002]In normal somatic cells, the telomere, which is located at the end of a chromosome, gets shortened at each time of cell mitosis. When the telomere is shortened to some level, the cell will lose the ability of replication and go into apoptosis stage. Telomerase, which is a ribonucleoprotein, acts on the telomere in a eukaryocyte, so as to prolong or maintain the length of the telomere. A telomerase mainly includes two portions; one is a protein sub-unit with activity of reverse transcription, i.e. the human telomerase reverse transcriptase (hTERT), and the other one is an RNA template for synthesizing repeated sequences of the telomerase, i.e. the human telomerase RNA component (hTR)...

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(United States)
IPC IPC(8): A61K31/498C07D235/00A61K31/4184C07D241/38A61P35/00A61K31/433C07D285/14
CPCC07D235/08C07D235/10C07D285/14C07D235/14C07D241/42C07D235/12A61P35/00
Inventor HUANG, HSU-SHAN
Owner NAT DEFENSE MEDICAL CENT
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