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A kind of indole-alpha-amino acid compound and its application in the preparation of anti-AIDS drugs

An amino acid and anti-AIDS technology, applied in the field of medicine, can solve problems such as complex structure, difficult synthesis, and poor activity

Active Publication Date: 2016-03-16
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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  • A kind of indole-alpha-amino acid compound and its application in the preparation of anti-AIDS drugs
  • A kind of indole-alpha-amino acid compound and its application in the preparation of anti-AIDS drugs
  • A kind of indole-alpha-amino acid compound and its application in the preparation of anti-AIDS drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Preparation of 2-amino-2-(6-bromo-1H-indol-3-yl)-3,3,3-trifluoropropionic acid ethyl ester (HX1)

[0040] Take 0.2 mmol of 6-bromoindole and 0.2 mmol of trifluoropropionate-imine into a single-neck round-bottomed flask containing a magnet, add 5 mL of dichloromethane to dissolve it, stir evenly, add 0.2 mmol AlCl 3The catalyzed Friedel-Crafts reaction was carried out, and the reaction was monitored by TLC. After the raw materials were fully reacted, the pure solid compound HX1 was obtained by column chromatography. The product was a yellow solid with a yield of 91%. 1 HNMR (400MHz, CDCl 3 )δ8.30(s, 1H), 7.76(d, J=8.7Hz, 1H), 7.47(s, 1H), 7.41(d, J=2.5Hz, 1H), 7.26–7.23(m, 1H), 4.45–4.36(m, 2H), 1.33(t, J=7.1Hz, 3H). 13 CNMR (101MHz, CDCl 3 )δ169.15,137.14,125.03,124.84,124.07,123.90,122.54,116.33,114.30,108.87,76.12(q),64.44,13.94.

Embodiment 2

[0041] Example 2: Preparation of 2-amino-2-(5-bromo-1H-indol-3-yl)-3,3,3-trifluoropropionic acid ethyl ester (HX2)

[0042] The preparation method was as in Example 1, and the product was a pale yellow solid with a yield of 91%. 1 HNMR (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, 3H), 1.28(t, J=7.1Hz, 3H). 13 CNMR (101MHz, CDCl 3 )δ169.09,135.02,127.65,126.78,125.65,125.29,123.94,113.94,112.79,108.33,64.52,62.69(q),13.92.

Embodiment 3

[0043] Example 3: Preparation of 2-amino-2-(6-fluoro-1H-indol-3-yl)-3,3,3-trifluoropropionic acid ethyl ester (HX3)

[0044] The preparation method is as in Example 1, the product is light yellow solid, and the yield is 89%. 1 HNMR (400MHz, Acetone-d 6 )δ10.64(s,1H),7.93–7.86(m,1H),7.59(s,1H),7.19(d,J=9.8Hz,1H),6.95–6.86(m,1H),4.37(dtt , J=10.8, 7.4, 3.7Hz, 2H), 1.29(t, J=7.1Hz, 3H). 13 CNMR (101MHz, Acetone-d 6 )δ169.09,160.54(d, 1 J C-F = 237.35Hz), 137.69, 126.59, 126.35, 123.22, 123.12, 109.81, 109.04(d, 2 J C-F = 24.24Hz), 98.35(d, 3 J C-F = 25.25Hz), 78.14, 63.67, 14.26.

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Abstract

The invention belongs to the technical field of medicine and particularly discloses indole-alpha-amino acid compounds. The idole-alpha-amino acid derivatives are prepared by carrying out Friedel-Crafts reaction on indole and trifluoropropionate-imine under the catalytic action of Lewis acid. The invention mainly discloses a method for preparing the compounds and an application of the compounds in preparation of anti-AIDS drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to an indole-α-amino acid compound and its application in the preparation of anti-AIDS drugs. Background technique [0002] Since the 1980s, Acquired Immunodeficiency Syndrome (AIDS) was first discovered and confirmed, it has spread rapidly in my country and the world, and it is a major epidemic disease that causes death worldwide. The latest data from the World Health Organization shows that about 3 million people have died of AIDS in the world, and 30 million patients are still fighting against AIDS. Therefore, the development of new high-efficiency and low-cost therapeutic drugs is still a top priority for 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/20C07D209/24A61K31/405A61P31/18
CPCC07D209/20C07D209/24
Inventor 周海兵吴叔文田波舒红兵韩欣吴浩明
Owner WUHAN UNIV
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