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M-bis(arene) polysubstituted amino benzene compound as non-nucleoside HIV reverse transcriptase inhibitor, and preparation and use thereof

一种化合物、烃基的技术，应用在杂环化合物有效成分、有机化学、抗病毒剂等方向，能够解决易产生耐药性等问题

Inactive Publication Date: 2009-04-15
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the main problem is that it is prone to drug resistance

Method used

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  • M-bis(arene) polysubstituted amino benzene compound as non-nucleoside HIV reverse transcriptase inhibitor, and preparation and use thereof
  • M-bis(arene) polysubstituted amino benzene compound as non-nucleoside HIV reverse transcriptase inhibitor, and preparation and use thereof
  • M-bis(arene) polysubstituted amino benzene compound as non-nucleoside HIV reverse transcriptase inhibitor, and preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0135] Preparation Example 1: 5-chloro-N-(4'-cyanophenyl)-2,4-dinitroaniline (IV-1)

[0136] 2,4-dichloro-1,5-dinitrobenzene (II-1, 1.2g, 5mmol) and p-cyanoaniline (III-1, 0.59g, 5mmol) were dissolved in N,N-dimethylformaldehyde Amide (DMF, 10 mL). Potassium tert-butoxide (1.4 g, 12.5 mmol) was added in batches while cooling in an ice-water bath, and then reacted at room temperature for 45 minutes. The reaction solution was poured into ice water, the pH value was adjusted to about 6 with dilute HCl, and stirred for 30 minutes to precipitate a solid. The solid was filtered out, washed with water until neutral, dried, and separated on a silica gel column (eluted with ethyl acetate:petroleum ether) to obtain compound VI-1 (1.44 g, 90%) as a pale yellow solid. 1 H NMR (CDCl 3 )δppm, 7.41 (1H, s, ArH-6), 7.57 (2H, d, J=8.7Hz, ArH-3', 5'), 7.91 (2H, d, J=8.7Hz, ArH-2', 6'), 8.90 (1H, s, ArH-3), 10.07 (1H, s, NH).

preparation Embodiment 2

[0137] Preparation Example 2: 5-chloro-2,4-dinitro-N-(4'-methoxyphenyl)-aniline (IV-2)

[0138] 2,4-dichloro-1,5-dinitrobenzene (II-1, 0.5 g, 2.11 mmol) and p-methoxyaniline (III-2, 0.26 g, 2.11 mmol) were dissolved in 5 mL DMSO, Join K 2 CO 3 (0.58g, 4.22mmol) and a catalytic amount of metal Cu were stirred and reacted at 115°C for 2 hours under the protection of nitrogen. Pour into ice water and stir to precipitate a solid. The solid was filtered out, washed with water for several times, dried, and separated on a silica gel column (petroleum ether / ethyl acetate), resulting in a reddish-brown solid (IV-2, 0.68g, 67%). 1 H NMR (CDCl 3 )δppm 3.88 (3H, s, OCH 3 ), 7.02 (1H, s, ArH-6), 7.03 (2H, d, J=8.96Hz, ArH-3', 5'), 7.21 (2H, d, J=8.96Hz, ArH-2', 6 '), 9.07 (1H, s, ArH-3), 9.73 (1H, s, NH).

preparation Embodiment 3

[0139] Preparation Example 3: 5-chloro-2,4-dinitro-N-(4'-methylphenyl)-aniline (IV-3)

[0140] The preparation method is the same as IV-2, and the yield is 70%. 1 H NMRδppm 2.08 (3H, s, CH 3 ), 6.86 (2H, d, J=8.12Hz, ArH-3', 5'), 7.03 (1H, s, ArH-6), 7.10 (2H, d, J=8.12Hz, ArH-2', 6 '), 9.16 (1H, s, ArH-3), 9.71 (1H, s, NH).

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Abstract

The invention relates to an m-arene 2-polysubstitution phenyl amines compound possessing anti HIV activity or medicinal salt thereof, wherein, definitions of X and R1-R7 are shown in a claim, and the invention also relates to a preparation method thereof, a drug combination containing the compounds and the application to anti HIV drug preparation thereof.

Description

Technical field: [0001] The present invention relates to m-diaryl hydrocarbon-multi-substituted aniline compounds with anti-HIV activity, a preparation method thereof, a pharmaceutical composition containing them and an application for preparing anti-HIV medicaments. Background technique [0002] HIV (HIV) is an RNA virus. The surface of the virus is a double lipid membrane. Two single-stranded RNAs and some important enzymes (such as reverse transcriptase, proteolytic enzyme, integrase) and structural proteins (p24, p17, p7, etc.) are wrapped in the membrane. There are two very important glycoproteins gp120 and gp41 on the membrane surface of the virus. gp120 is on the outside of the membrane, and gp41 spans the double lipid membrane and forms a complex with gp120. Their main function is to recognize and attack cells with CD4 surface receptors in the human immune system, such as lymphocytes (T cells), macrophages, etc. HIV cannot reproduce outside the body and must rely...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/58C07C255/59C07D307/46A61K31/277A61K31/34A61P31/18
CPCC07C255/59C07C255/58C07C217/92C07D307/46A61P31/18
Inventor 谢蓝秦炳杰李国雄姜世勃陆虹
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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