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Novel phenazine substance, preparation method and application thereof

A technology of phenazine and substances, which is applied in the direction of medical preparations containing active ingredients, drug combinations, and pharmaceutical formulas, can solve the problems of low activity, poor selectivity, and high toxicity of anticancer drugs, and achieve significant anticancer activity and selectivity. Sex enhancement, less toxic effects

Active Publication Date: 2017-04-05
陆源
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the defects of low activity, high toxicity and poor selectivity of anticancer drugs in the prior art, the present invention provides a new phenazine substance, its preparation method and its application

Method used

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  • Novel phenazine substance, preparation method and application thereof
  • Novel phenazine substance, preparation method and application thereof
  • Novel phenazine substance, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of 2-chloroacetamide-phenazine:

[0043]

[0044] Step 1: Synthesis of intermediate 2-amino-phenazine:

[0045]

[0046]Put 1.3g (0.01mol) of aniline hydrochloride, 1.4g (0.01mol) of o-nitroaniline and 4g (0.03mol) of zinc chloride in a reaction kettle, stir and react at 180-185°C for 30min, and start to react naturally after the reaction is over. Cool, cool to 100°C and extract twice with 20ml of ethanol under reflux, each extraction for 30min, then neutralize with saturated aqueous sodium carbonate solution, a solid precipitates, filter to take the filter cake, wash with dilute hydrochloric acid and methanol in turn, and vacuum dry to obtain Crude magenta solid 0.9g, yield 46.2%. mp:285-286℃(DEC); Infrared (KBr,cm -1 ):3307, 3190, 2915, 1640, 1598, 1512, 1474, 1456, 1335, 1236, 1130, 827, 755; 1 H-NMR (DMSO-d 6, 300MHz) δ: 8.05(m,2H,Ar-H), 7.89(m,2H,Ar-H), 7.79(dd,1H,Ar-H), 7.63(d,1H,Ar-H), 7.28( dd,1H,Ar-H), 5.25(s,2H,NH 2 ). 13 C-NMR (DMSO-d ...

Embodiment 2

[0051] Synthesis of N-[chloromethylamine]phenazine-2-carboxamide:

[0052]

[0053] Step 1: Synthesis of intermediate phenazine-2-carboxylic acid:

[0054]

[0055] Put 1.4g (0.01mol) of o-nitroaniline, 1.4g (0.01mol) of methyl benzoate and 4g (0.03mol) of catalyst zinc chloride in a reaction kettle and stir at 190-200°C for 30 minutes. After the reaction, start Natural cooling, cooling to 100°C, adding excess sodium hydroxide aqueous solution to hydrolyze it into phenazine-2-carboxylic acid, and forming a salt with sodium hydroxide, filtering to get the filtrate, adding excess hydrochloric acid aqueous solution to precipitate, separate and purify, and obtain the crude product White solid 0.7g, yield 30%. mp>300℃(DEC); 1 H-NMR (DMSO-d 6 ,300MHz) δ: 12.73(s,1H,OH), 9.44(d,1H,Ar-H), 9.05(d,1H,Ar-H), 8.38(d,1H,Ar-H), 8.27(m , 2H, Ar-H), 8.12 (m, 2H, Ar-H). 13 C-NMR (DMSO-d 6 ,125MHz) δ: 166.4(CO), 144.1(Ar-C), 142.4(Ar-C), 142.2(Ar-C), 142.1(Ar-C), 139.7(Ar-C), 132.3(...

Embodiment 3

[0060] Synthesis of 2-chloroacetamide-4-methyl-phenazine:

[0061]

[0062] Step 1: Synthesis of intermediate 2-amino-4-methyl-phenazine:

[0063]

[0064] Put 1.4g (0.01mol) of 3-methylaniline hydrochloride, 1.4g (0.01mol) of o-nitroaniline and 4g (0.03mol) of zinc chloride in a reaction kettle, and stir and react at 180-185°C for 30min After the reaction, start to cool naturally, cool to 100°C and use 20ml ethanol to reflux and extract twice for 30min, then neutralize with saturated aqueous sodium carbonate solution, solids are precipitated, filter to get the filter cake, and after treatment, 0.8g of crude brown solid is obtained. rate 38.3%. mp>300℃(DEC); 1 H-NMR (DMSO-d 6 ,300MHz)δ:8.33(m,2H,Ar-H), 8.18(m,2H,Ar-H), 7.81(d,1H,Ar-H), 7.47(d,1H,Ar-H), 5.32 (s,2H,NH 2 ), 2.32(s,3H,CH 3 ). 13 C-NMR (DMSO-d 6 ,125MHz) δ: 146.7(Ar-C), 144.2(Ar-C), 143.1(Ar-C), 142.3(Ar-C), 142.2(Ar-C), 138.0(Ar-C), 136.1(Ar -C), 129.7(Ar-C), 129.6(Ar-C), 129.3(Ar-C), 129.2(Ar-C), 1...

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Abstract

The invention discloses a novel phenazine substance, a preparation method and an application thereof. The novel phenazine substance is a compound represented as the general formula (1), or a medically acceptable salt thereof, or a hydrate of the medically acceptable salt thereof, wherein n is 0 or 1, X is -NHCO- or -CONH-; R is halogen or a hydroxyl group; R1, R2 and R3 are same or different and are independently represented as hydrogen, an amino group, a hydroxyl group, a methyl group, a methoxyl group or -COOCH3; R4, R5, R6 and R7 are same or different and are independently represented as hydrogen, an amino group, a hydroxyl group, a methyl group, a methoxyl group, -COOCH3, halogen, a carboxyl group, or a halogenated methyl group; wherein the general formula (1) excludes the following situation: when n is 1 and x is the -NHCO-, R2 is a hydroxyl group, and R1, R3, R4, R5, R6 and R7 are all hydrogen. The novel phenazine substance, compared with an anticancer medicine or other phenazine substances in the prior art, has higher anticancer activity, lower toxicity and higher selectivity.

Description

technical field [0001] The invention relates to a novel phenazine substance, a preparation method and application thereof, and belongs to the field of compounds. Background technique [0002] For a long time, cancer has become a major disease that endangers human life and health. According to statistics, cancer has become the leading cause of death among Chinese residents, and there are about 4 million new cancer patients in the world every year. The research and development of anticancer drugs has always been a hot spot for researchers. Finding anticancer drugs with high efficiency, high selectivity, and less toxic side effects is an important direction of drug research and development. [0003] Topoisomerase 1 and 2 play an important role in the process of DNA replication and transcription. They maintain the topology of DNA through continuous DNA splicing and rejoining, so that DNA replication and transcription can run smoothly. Human topoisomerase is highly expressed i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/46A61K31/498A61P35/00A61P35/02A61P31/12A61P31/04
CPCC07D241/46
Inventor 陆源李芸
Owner 陆源
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