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Fully substituted 3-nitroindole compound and its intermediate compound, preparation method and application

A nitroindole compound and a fully substituted technology, applied in the field of medicinal chemistry, can solve the problems of complex and difficult fully substituted indole compounds, and achieve the effects of simple operation, high yield and mild reaction conditions

Active Publication Date: 2019-03-08
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of multi-substituted indoles usually requires complex steps or metal catalysis, and it is even more difficult to achieve fully substituted indoles.

Method used

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  • Fully substituted 3-nitroindole compound and its intermediate compound, preparation method and application
  • Fully substituted 3-nitroindole compound and its intermediate compound, preparation method and application
  • Fully substituted 3-nitroindole compound and its intermediate compound, preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Example 1: Synthesis of 1,1-bis((4-methoxybenzyl)amino)-2-nitroethylene (compound 1): 1,1-bis(methylmercapto)-2-nitroethylene ( 1.65g, 10mmol) was dissolved in 80ml of ethanol, stirred for 2 minutes, another raw material arylamine compound 4-methoxybenzylamine (3.43g, 25mmol) was added, heated to reflux for 12h, a white solid was precipitated, and the solid was Suction filtration and washing to obtain the target material (1), 1,1-bis((4-methoxybenzyl)amino)-2-nitroethylene (compound 1), yield 92%, melting point: 226.8-227.2 ℃.

[0103] Proton NMR spectrum (deuterated dimethyl sulfoxide, Bruker AM 600 instrument): δ=3.76(s, 3H, CH 3 ),3.75(s,3H,CH 3 ),4.29(s,2H,CH 2 ),4.51(s,2H,CH 2), 6.41 (s, 1H, CH), 6.91–7.30 (m, 8H, ArH), 7.89 (s, 1H, NH), 10.31 (s, 1H, NH).

Embodiment 2

[0104] Example 2: Synthesis of 1,1-bis((4-methylphenethyl)amino)-2-nitroethylene (compound 2): 1,1-bis(methylmercapto)-2-nitroethylene ( 1.65g, 10mmol) was dissolved in 50ml of ethanol, stirred for 2 minutes, another raw material arylamine compound 4-methylphenethylamine (3.38g, 25mmol) was added, heated to reflux for 24h, a white solid was precipitated, and the solid was Suction filtration and washing to obtain the target raw material (2), 1,1-bis((4-methylphenethyl)amino)-2-nitroethylene (compound 2), yield 90%, melting point: 215.3-215.7 ℃.

[0105] Proton NMR spectrum (deuterated dimethyl sulfoxide, Bruker AM 600 instrument): δ=2.25–2.29(m,6H,CH 3 ),2.74–2.77(m,4H,CH 2 ),3.36(s,4H,NHCH 2 ), 6.55 (s, 1H, CH), 7.11-7.14 (m, 8H, ArH), 7.19 (s, 1H, NH), 10.10 (s, 1H, NH).

Embodiment 3

[0106] Example 3: Synthesis of 1,1-bis((4-fluorophenethyl)amino)-2-nitroethylene (compound 3): 1,1-bis(methylmercapto)-2-nitroethylene (1.65 g, 10mmol) was dissolved in 60 ml of ethanol, stirred for 2 minutes, another raw material arylamine compound 4-fluorophenethylamine (2.78g, 20mmol) was added, heated to reflux for 18h, a white solid was precipitated, and the solid was filtered by suction , and washed to obtain the target material (3), 1,1-bis((4-fluorophenethyl)amino)-2-nitroethylene (compound 3), with a yield of 90% and a melting point of 159.2-159.6°C.

[0107] Proton NMR spectrum (deuterated dimethyl sulfoxide, Bruker AM 600 instrument): δ=2.79–2.82(m,4H,CH 2 ),3.35–3.43(m,4H,CH 2 ), 6.57 (s, 1H, CH), 7.12-7.30 (m, 8H, ArH), 7.30 (br, 1H, NH), 10.12 (br, 1H, NH).

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Abstract

The invention relates to a fully-substituted 3-nitroindole compound as well as a preparation method and application of the fully-substituted 3-nitroindole compound and belongs to the technical field of pharmaceutical chemistry. The compound has a structure shown as a formula (I): the formula (I) is shown in the description; an intermediate has a general structure shown as a formula (II): the formula (II) is shown in the description. A synthesis method of the fully-substituted 3-nitroindole compound and the intermediate of the fully-substituted 3-nitroindole compound, disclosed by the invention, has the characteristics of easiness of obtaining raw materials, moderate reaction conditions, short reaction steps, high yield, low synthetic cost and the like, and is especially suitable for industrial production. The structure of the fully-substituted 3-nitroindole compound has a plurality of fluorine atoms; the fluorine element is introduced so that the bioactivity of the compound is doubled; meanwhile, nitro of the compound is easily subjected to functional group transformation and a foundation is laid for further result modification. The fully-substituted 3-nitroindole compound has various potential pharmaceutical activities. The anti-tumor activity of the fully-substituted 3-nitroindole compound is primarily researched. A research shows that one part of the compound has certain anti-tumor activity and has a wide application prospect.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to a fully substituted 3-nitroindole compound with antitumor activity, an intermediate compound thereof, a preparation method and an application thereof. Background technique [0002] Tumor is a disease that seriously threatens human life and health in the world today. It has become the number one killer of death, and more and more people are taking more lives. Therefore, the treatment and prevention of tumors has attracted widespread attention from the whole society. In the treatment and prevention of tumors, chemotherapy, which uses natural or synthetic compounds to block, reverse or prevent the occurrence of aggressive tumors, is the most widely used and effective clinical tumor treatment. [0003] Indole has good biological activity, such as anti-tumor, anti-HIV, malaria and so on. Although indole compounds are widely distributed in natural products, bec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/40C07D405/14C07D409/14C07D471/04C07C217/58C07C213/02C07C211/27C07C211/29C07C209/60C07D317/58C07D333/20C07D307/14A61P35/00
CPCC07C209/60C07C211/27C07C211/29C07C213/02C07C217/58C07D209/40C07D307/14C07D317/58C07D333/20C07D405/14C07D409/14C07D471/04
Inventor 严胜骄林军胡兴梅罗大云资全兴崔时胜
Owner YUNNAN UNIV
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