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
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0025]Alternatively, in some steps of the above-mentioned methods, the production rate will increase if the solvents used for dissolving the diaminoanthraquinone contain less water. In the purification steps for the products, alcohol could be used for crystallization; alternatively, hot alcohol could be used for washing the products. The products with high solubility could be dissolved in alcohol before crystallization. The products with low solubility need to be washed by hot alcohol to wash out initial material or impurities and by-products generated in the reaction. Compared with recrystallization, although parts of products would be lost in the washing steps, it would be easier to obtain the purified products.

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

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  • 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...

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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

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Application Information

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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
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