Preparation and application of bismethoxyl substituted carbazole compound with anti-HIV activity

A technology of bismethoxy, aniline compounds, applied in the direction of organic active ingredients, medical preparations containing active ingredients, organic chemistry, etc., can solve problems to be proved and so on

Pending Publication Date: 2019-02-22
YUNNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Another strategy, which has mainly made progress in academia, is the development of molecules capable of interacting with multiple targets simultaneously (Drug Discov. Today, 2004, 9, 641.; Med. Chem., 2014, 22, 4658.), however , the feasibility of this approach, such as a 'shock and kill' strategy, remains to be proven (Nature, 2012, 487, 439.; AIDS model. PLoS Pathog., 2012, 8, e1002774.)

Method used

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  • Preparation and application of bismethoxyl substituted carbazole compound with anti-HIV activity
  • Preparation and application of bismethoxyl substituted carbazole compound with anti-HIV activity
  • Preparation and application of bismethoxyl substituted carbazole compound with anti-HIV activity

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0072] Preparation Example 1: Synthesis of 3,5-dimethoxy-N-(3-methoxyphenyl)aniline.

[0073]

[0074] Take m-bromoanisole (0.187g, 1.0mmol), 3,5-dimethoxyaniline (0.183g, 1.2mmol), cesium carbonate (0.390g, 1.2mmol), 1,1'-binaphthyl-2 , 2'-bisdiphenylphosphine (0.049g, 0.08mmol), palladium acetate (0.011g, 0.05mmol) in a 50mL round bottom flask, add about 25mL of toluene, fill with nitrogen protection, reflux at 120 ° C and stir the reaction To the end of the reaction (TLC tracking reaction). After the reaction, the reaction system was cooled to room temperature, and the solvent was evaporated to dryness using a rotary evaporator, extracted three times with ethyl acetate (5mL×3), the ethyl acetate phase was combined, the organic phase was collected, and anhydrous Na 2 SO 4 After drying, the ethyl acetate layer was evaporated to dryness with a rotary evaporator, and purified by silica gel column chromatography to obtain the target product, 225.7 mg of white crystals, with...

Embodiment 1

[0075] The nuclear magnetic data of embodiment 1 product is as follows:

[0076] 1 H NMR (300 MHz, CDCl 3 ) δ7.24–7.13 (m, 1H), 6.76–6.63 (m, 2H), 6.52 (dd, J = 8.2, 2.3,Hz, 1H), 6.27–6.24 (m, 2H), 6.10–6.08 (m, 1H), 5.75 (s, 1H), 3.78(s, 3H), 3.76 (s, 6H). 13 C NMR (75 MHz, CDCl 3 ) δ 161.85, 160.89, 145.19, 144.27, 130.35, 111.28, 106.99, 104.45, 96.44, 93.52, 55.56, 55.47.

preparation Embodiment 2

[0077] Preparation Example 2: Synthesis of 3,5-dimethoxy-N-(4-methoxyphenyl)aniline.

[0078]

[0079] Using p-bromoanisole (0.187g, 1.0mmol) and 3,5-dimethoxyaniline (0.183g, 1.2mmol) as raw materials, the preparation method was the same as in Example 1 to obtain 206.4mg of a colorless oily liquid with a yield of 80 %.

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PUM

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Abstract

The invention relates to the field of biomedicines and provides an application of a novel carbazole derivative with anti-HIV activity in preparing an anti-HIV drug. The invention particularly relatesto a compound as shown in a formula (I) and pharmaceutical salt thereof. The compound or the pharmaceutical salt thereof can be also combined with pharmaceutical auxiliary materials to prepare a single formula or a compound preparation. The invention also discloses an application of the compound or the pharmaceutical salt thereof in preparing a drug for preventing or treating HIV infection relateddiseases or symptoms. The preparation raw materials of the compound are high in commercial degree and cheap and easily available. The preparation route is short, the method is simple, the productioncost is low, and more efficient and safe candidate drugs are provided for clinical anti-HIV treatment.

Description

technical field [0001] The present invention relates to a class of compounds with the activity of inhibiting human immunodeficiency virus (HIV), especially the preparation and use of a bismethoxy substituted carbazole compound with anti-HIV activity. Background technique [0002] Human immunodeficiency virus (HIV) is the main cause of acquired immunodeficiency syndrome (AIDS), and it remains an important cause of death from the disease worldwide (Nature 2001, 410 , 968.; Advanced Drug Delivery Reviews, 2010, 62(4- 5), 491.). HIV primarily targets immune cells, the CD 4+ T cells, monocytes, macrophages and dendritic cells (Journal of Controlled Release, 2014, 192, 271.). Although AIDS was introduced in 2000 as one of the health goals of the United Nations Millennium Development Goals, it remains an unresolved problem. In fact, there are nearly 37 million AIDS patients worldwide, with more than 2 million new infections each year (Drug Discovery Today, 2018, 23(2), 206.). ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/88A61K31/403A61P31/18
CPCA61P31/18C07D209/88
Inventor 汪云松杨靖华蒋涛
Owner YUNNAN UNIV
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