Substituted benzoheterocyclic compounds and preparation method and application thereof

A compound and unsubstituted technology, applied in the field of substituted benzoheterocyclic compounds and their synthesis

Active Publication Date: 2013-03-06
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Before, there was no literature report on any biological activity of this compound, and this patent discovered the medicinal possibility of the above compound for the first time

Method used

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  • Substituted benzoheterocyclic compounds and preparation method and application thereof
  • Substituted benzoheterocyclic compounds and preparation method and application thereof
  • Substituted benzoheterocyclic compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0223] (Z)-2-azido-3-(4-acetamidophenyl) methyl acrylate (2a)

[0224] 4-Acetaminobenzaldehyde (2g, 0.0122mol) was dissolved in methanol (30ml), sodium methoxide (0.85g, 0.0159mol) was added, and methyl azide acetate in methanol (1.65g, 0.0128mol) was added dropwise at room temperature, After dropping, react at room temperature for 1.5h. After the reaction was completed, the reaction solution was added to saturated ammonium chloride solution, extracted with ethyl acetate (3×50ml), and the organic layers were combined. Wash the organic layer with saturated brine, anhydrous MgSO 4 Dry overnight. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent, and the residue was passed through a column to obtain a pale yellow solid (2.7 g, 85%). Because the compound is unstable, it has not been characterized by NMR.

Embodiment 2

[0226] Methyl 6-acetylaminoindole-2-carboxylate (3a)

[0227] Compound 2a (2.7g, 0.0104mol) was dissolved in chlorobenzene (50ml) and heated to reflux for 2.5h. After the reaction was completed, a white solid precipitated out after cooling, and the target product was obtained by filtration, a white solid (2.08 g, 86%). 1 H-NMR(400M,DMSO-d 6 )δ(ppm): 2.05(s, 3H), 3.83(s, 3H), 7.07(s, 1H), 7.10(d, J=8.8Hz, 1H), 7.52(d, J=8.8Hz, 1H) ,8.01(s,1H),9.96(s,1H),11.75(s,1H).

Embodiment 3

[0229] Methyl 6-aminoindole-2-carboxylate (3b)

[0230] Compound 3a (1g, 4.31mmol) was dissolved in a methanol solution of hydrogen chloride, and the mixture was heated to reflux for 2h. After the reaction was completed, the solvent was evaporated under pressure, and the residue was recrystallized from anhydrous methanol to obtain a white solid (0.37 g, 78%). 1 H-NMR(400M,DMSO-d 6 )δ(ppm): 3.87(s,3H), 6.94(d,J=8.4Hz,1H), 7.16(s,1H), 7.32(s,1H), 7.68(d,J=8.4Hz,1H) ,9.49(br,2H),11.99(s,1H).

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Abstract

The invention provides substituted benzoheterocyclic compounds and a preparation method thereof. The compounds have structures shown by formulas I and II. The invention also provides the effects of the compounds shown by formulas I and II in resisting virus, tumor and the like. The invention further provides a medicine composition taking the compounds shown by the formulas I and II as active ingredients, and the anti-virus or anti-tumor effect of the medicine composition. The invention lays a foundation for the future in-depth study and development of the anti-virus or anti-tumor medicine of the compounds.

Description

Technical field [0001] The present invention relates to a group of substituted benzoheterocyclic compounds and a synthesis method thereof, and also relates to the application of the compound in antiviral and antitumor aspects, a pharmaceutical composition containing the compound as an active component and the application thereof. Background technique [0002] During the extensive screening of antiviral active compounds, 4-benzyloxy-6-aminoindole-2-carboxylic acid methyl ester was found from the compound sample library established by the Pharmaceutical Biotechnology Laboratory of the Chinese Academy of Medical Sciences (as shown below ) It has obvious anti-influenza virus and anti-tumor activity. Previously, there was no literature report on any biological activity of this compound. This patent discovered the medicinal potential of the above compound for the first time. The present invention also uses this compound as a lead, designs and synthesizes a series of 2,3,4,5,6,7-positi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/42C07D307/85C07D333/70C07D209/12C07D401/04C07D209/18C07D209/08C07D215/48C07D215/54C07D215/50C07D215/38A61K31/404A61K31/343A61K31/381A61K31/496A61K31/454A61K31/47A61P35/00A61P31/18A61P31/16
Inventor 李卓荣季兴跃薛司徒陶佩珍王真
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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