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Indole compound and application thereof as HIV-1 reverse transcriptase inhibitor

A technology of compounds and indoles, applied in the field of medicine, can solve the problems of complex structure, difficult synthesis, and not particularly good activity.

Inactive Publication Date: 2013-05-22
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Recently, it has been reported in the literature that some indole compounds have certain anti-HIV reverse transcriptase activity, but most of them have complex structures, are difficult to synthesize, and their activities are not particularly good, which limits their possibility of becoming a drug

Method used

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  • Indole compound and application thereof as HIV-1 reverse transcriptase inhibitor
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  • Indole compound and application thereof as HIV-1 reverse transcriptase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1: Preparation of ethyl 2-(5-nitro-1H-indol-3-yl)-2-hydroxy-3,3,3-trifluoropropionate (HX1)

[0037] Take 0.2mmol of 5-nitroindole and 0.2mmol of trifluoropyruvate into a single-necked round-bottomed flask containing a magnet, add 5mL of dichloromethane to dissolve, stir well, add 0.2mmol of AlCl 3 The Friedel-Crafts reaction was catalyzed, and the reaction was monitored by TLC. After the raw materials were fully reacted, the pure solid compound HX1 was separated by column chromatography, and the product was a yellow solid with a yield of 88%. 1 H NMR (400MHz, Acetone-d 6 )δ11.09(s,1H),8.85(d,J=1.7Hz,1H),7.96(dd,J=9.0,2.2Hz,1H),7.74(s,1H),7.53(d,J=9.0 Hz,1H),4.33–4.23(m,2H),1.20(t,J=7.1Hz,3H). 13 C NMR (101MHz, Acetone-d 6) δ 168.69, 142.80, 140.78, 129.76, 129.60, 126.41, 125.72, 119.27, 118.07, 113.13, 112.07, 64.07, 14.20.

Embodiment 2

[0038] Example 2: Preparation of ethyl 2-(5-fluoro-1H-indol-3-yl)-2-hydroxy-3,3,3-trifluoropropionate (HX2)

[0039] The preparation method was as in Example 1, and the product was a white solid with a yield of 90%. 1 H NMR (400MHz, CDCl 3 )δ8.38(s,1H),7.57(d,J=10.3Hz,1H),7.42(s,1H),7.20(s,1H),6.95(t,J=9.0Hz,1H),4.40( dq,J=20.9Hz,3H),1.33(t,J=7.1Hz,3H). 13 C NMR (101MHz, CDCl 3 )δ 169.19, 159.28, 132.90, 126.16, 125.57, 125.47, 124.93, 122.08, 112.14, 112.04, 111.38, 111.12, 108.67, 108.62, 106.40, 106.15, 64.42, 13.86.

Embodiment 3

[0040] Example 3: Preparation of ethyl 2-(5-chloro-1H-indol-3-yl)-2-hydroxy-3,3,3-trifluoropropionate (HX3)

[0041] The preparation method was as in Example 1, and the product was a white solid with a yield of 87%. 1 H NMR (400MHz, CDCl 3 )δ8.34(s,1H),8.00(s,1H),7.35(s,1H),7.18(d,J=10.3Hz,1H),7.11(d,J=8.6Hz,1H),4.40– 4.27(m,2H),1.28(t,J=7.1Hz,3H). 13 C NMR (101MHz, CDCl 3 ) δ 169.09, 135.03, 126.78, 125.70, 125.63, 124.82, 123.90, 121.97, 113.91, 112.81, 108.28, 64.51, 13.89.

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Abstract

The invention belongs to the field of medical technology, and specifically discloses an indole compound and an application thereof as an HIV-1 reverse transcriptase inhibitor. The indole compound disclosed by the invention has a structural general formula: wherein the formula is described in the specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to an indole compound and its application as an HIV-1 reverse transcriptase inhibitor. Background technique [0002] Acquired Immunodeficiency Syndrome (AIDS) is prevalent in the world and in my country, and it is a major epidemic disease that causes death worldwide. The latest figures from World Guardian show that about 3 million people worldwide have died from AIDS, and there are still 30 million patients who are still struggling with AIDS. Therefore, the research and development of efficient and cheap therapeutic drugs is still an urgent task in the prevention and treatment of AIDS. Human immunodeficiency virus type 1 (HIV-1) is the pathogenic factor that causes acquired immunodeficiency syndrome. After the virus infects the host, it mainly uses reverse transcriptase, integrase and protease to complete its replication cycle. Because HIV is constantly mutating during the replicat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/18C07D209/24A61K31/405A61P31/18
Inventor 吴叔文周海兵田波董春娥欧阳文杰韩欣
Owner WUHAN UNIV
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