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4-(benzothiazole-2-yl)-N-substituted aniline compound and preparation method and application thereof

A technology for benzothiazoles and compounds, applied in the field of 4--N-substituted aniline compounds and their preparation, to achieve novel structures, significant effects, and remarkable antiviral effects

Active Publication Date: 2021-11-09
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, no specific drugs or vaccines have been approved for the prevention or treatment of MERS-CoV infection, and many basic and clinical studies on anti-MERS-CoV drugs are in progress

Method used

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  • 4-(benzothiazole-2-yl)-N-substituted aniline compound and preparation method and application thereof
  • 4-(benzothiazole-2-yl)-N-substituted aniline compound and preparation method and application thereof
  • 4-(benzothiazole-2-yl)-N-substituted aniline compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Embodiment 1: Compound Ia (R 1 = H, R 2 = H, R 3 = cyclohexyl) synthesis

[0085] Dissolve 4-(benzothiazol-2-yl)aniline (100mg, 0.44mmol) in DMF (3mL), add sodium hydride (105mg, 4.4mmol) and bromocyclohexane (80mg, 0.49mmol), 60 Reaction at ℃ for 5h. Cool down to room temperature, add water, extract with ethyl acetate, wash with saturated brine, separate layers, dry over anhydrous sodium sulfate, filter, and remove the solvent. The obtained crude product was subjected to silica gel column chromatography (eluent: petroleum ether / ethyl acetate = 30:1) to obtain 30 mg of white solid product Ia. 1 HNMR (400MHz, CDCl 3 )δ7.98(d, J=8.0Hz, 1H), 7.89 (d, J=8.8Hz, 2H), 7.84(d, J=7.9Hz, 1H), 7.45–7.41(m, 1H), 7.32– 7.28(m,1H), 6.62(d,J=8.9Hz,2H),3.98(d,J=6.5Hz,1H),3.37–3.34(m,1H),1.45–1.41(m, 2H),1.81 –1.76(m,2H),1.72–1.66(m,1H),1.46–1.35(m,2H),1.29–1.16(m,3H). 13 CNMR (101MHz, CDCl 3 )δ167.75, 153.34, 148.72, 133.46, 128.14, 124.92, 123.14, 121.24, 121.00, 120.30, 111....

Embodiment 2

[0086] Embodiment 2: Compound Ib (R 1 = H, R 2 = H, R 3＝ )Synthesis

[0087] The raw material bromocyclohexane in Example 1 was replaced by 2-(bromomethyl)-6-methoxyphenol, and the yellow solid compound Ib was obtained with reference to the method of Example 1. 1 HNMR (400MHz, DMSO-d 6 )δ8.79(s,1H), 8.00(d,J=7.4Hz,1H),7.89(d,J=8.1Hz,1H),7.78(d,J=8.4Hz,2H),7.46– 7.43( m,1H),7.35–7.31(m,1H),6.88–6.84(m,2H),6.82–6.80(m,1H),6.73–6.68(m,3H),4.30(d,J=5.9Hz, 2H),3.80(s,3H). 13 CNMR (101MHz, DMSO-d 6 )δ 168.00,153.86,151.61,147.29,143.82,133.68,128.60,126.17,125.51,124.26, 121.82,121.70,120.04,120.02,118.62,111.83,110.77.38,40.55

Embodiment 3

[0088] Embodiment 3: compound Ic (R 1 = H, R 2 = H, R 3 = )Synthesis

[0089] In embodiment 1, raw material bromocyclohexane is replaced by 3-bromomethylthiophene, and the experimental method of reference embodiment 1 obtains white solid compound Ic. 1 HNMR (400MHz, CDCl 3 )δ7.99(d, J=8.1Hz, 1H), 7.92(d, J=8.5Hz, 2H), 7.84(d, J=7.9Hz, 1H), 7.46–7.42(m, 1H), 7.36– 7.28(m, 2H), 7.21(s, 1H), 7.09(d, J=4.8Hz, 1H), 6.70(d, J=8.5Hz, 2H), 4.41(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ168.60, 154.34, 150.26, 139.54, 134.57, 129.14, 126.99, 126.49, 126.03, 124.33, 123.06, 122.40, 122.03, 121.39, 112.60, 43.31.

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Abstract

The invention provides a 4-(benzothiazole-2-yl)-N-substituted aniline compound and a preparation method thereof. The method comprises the steps of: reacting substituted 4-(benzothiazole-2-yl) aniline with a halide to generate the 4-(benzothiazole-2-yl)-N-substituted aniline compound, or reacting substituted 4-(benzothiazole-2-yl) aniline with halogenated acyl chloride, and carrying out nucleophilic substitution, reduction and nucleophilic substitution reactions to generate a series of 4-(benzothiazole-2-yl)-N-heterocyclic alkyl substituted aniline compounds. The invention also provides an application of the 4-(benzothiazole-2-yl)-N-substituted aniline compound in resisting middle east respiratory syndrome coronavirus (MERS-CoV) and novel coronavirus (SARS-CoV-2). The 4-(benzothiazole-2-yl)-N-substituted aniline compound has an application prospect in the field of discovery of new drugs for inhibiting the coronavirus.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and relates to a class of 4-(benzothiazol-2-yl)-N-substituted aniline compounds and a preparation method and application thereof. Background technique [0002] Middle East respiratory syndrome coronavirus (MERS-CoV) is a novel zoonotic viral pathogen in the Middle East. The viral infectious disease caused by this coronavirus infection is called Middle East respiratory syndrome (MERS). [0003] In September 2012, the novel coronavirus was found in a 60-year-old Saudi man with acute pneumonia and acute renal failure. As of May 31, 2019, at least 27 countries around the world have reported people infected with MERS-CoV, and 2,442 people have been infected with the virus, of which 842 died, with a fatality rate as high as 35%. The MERS virus was transmitted to humans through animals and subsequently spread from person to person. After infection with the virus, it can cause severe respi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C07D417/12A61P31/14
CPCC07D277/66C07D417/12A61P31/14Y02A50/30
Inventor 左建平汤杰唐炜杨帆胡玟奇童贤崑周宇林颖何佩岚张颖朱峰华于丽芳冯春兰
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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