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2, 2-disubstituted indoline-3-ketone alkaloid as well as preparation method and application thereof

A technology of indoline and alkaloids, applied in organic chemistry, antibacterial drugs, etc., can solve the problems of industrial application limitations, toxicity, etc., and achieve the effects of simple operation, wide substrate range, and mild conditions

Active Publication Date: 2021-11-26
XUCHANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, oxidative dearomatization-nucleophilic addition of indole substrates has become a new strategy for constructing such structures. However, the new strategies reported so far have the following disadvantages: the use of toxic nitrogen-oxides and Its salts, expensive photocatalysts or dangerous peroxides are used as oxidants, and its nucleophiles are also traditional negative electron aromatics, ketones, aldehydes or relatively expensive boron compounds, which limits its industrial application

Method used

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  • 2, 2-disubstituted indoline-3-ketone alkaloid as well as preparation method and application thereof
  • 2, 2-disubstituted indoline-3-ketone alkaloid as well as preparation method and application thereof
  • 2, 2-disubstituted indoline-3-ketone alkaloid as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Preparation of 2-phenyl-2-(2-quinolylmethyl)indolin-3-one:

[0055] 2-Phenylindole (38.6mg, 0.2mmol) was placed in a 10ml dry round-bottomed flask containing a magneton, and anhydrous ethyl acetate (4ml), cuprous chloride (2.0mg, 0.02mmol), 2-Methylquinoline III (57.3mg, 0.4mmol), pivalic acid (2.2mg, 0.02mmol), the air in the reaction flask was replaced with a three-way connection with a high-purity oxygen balloon, and placed under oxygen conditions , in an oil bath at 50°C, the reaction was stirred until the raw materials disappeared, the solvent was directly distilled off under reduced pressure, and the residue was directly purified by column chromatography to obtain pure product 1. 1 H NMR (400MHz, CDCl 3 )δ8.04(d, J=8.3Hz, 1H), 7.90(d, J=8.4Hz, 1H), 7.70(t, J=7.7Hz, 4H), 7.59(d, J=7.7Hz, 1H) ,7.47(td,J=8.2,1.1Hz,2H),7.23(t,J=7.4Hz,2H),7.19–7.06(m,3H),7.03(d,J=8.3Hz,1H),6.80( t, J=7.4Hz, 1H), 3.85(d, J=14.1Hz, 1H), 3.47(d, J=14.1Hz, 1H); 13 C NMR (101MHz, CDCl ...

Embodiment 2

[0057] Preparation of 3-methyl-2-phenyl-2-(2-quinolylmethyl)indolin-3-one:

[0058] With reference to the method of embodiment 1. 11 H NMR (400MHz, CDCl 3 )δ8.05(dd, J=11.9,6.8Hz,2H),7.90(d,J=8.4Hz,1H),7.70(dd,J=7.4,5.5Hz,5H),7.49(q,J=7.7 Hz, 2H), 7.31(dd, J=8.0, 6.4Hz, 2H), 7.23(t, J=7.5Hz, 2H), 7.15(t, J=7.3Hz, 1H), 7.09(d, J=8.4 Hz, 2H), 6.85(d, J=8.2Hz, 1H), 6.54(d, J=7.2Hz, 1H), 3.85(d, J=14.1Hz, 1H), 3.46(d, J=14.1Hz, 1H),2.55(s,3H); 13 C NMR (101MHz, CDCl 3 )δ202.65,161.46,158.14,147.55,140.77,139.17,137.02,136.53,129.76,128.96,128.43,127.79,127.43,126.97,126.40,125.93,123.17,122.22,120.64,110.42,71.50,46.23,18.45。

Embodiment 3

[0060] Preparation of 5-methyl-2-phenyl-2-(2-quinolylmethyl)indolin-3-one:

[0061] With reference to the method of embodiment 1. 1 H NMR (400MHz, CDCl 3 )δ8.03(d, J=8.5Hz, 1H), 7.87(d, J=8.4Hz, 1H), 7.72–7.62(m, 4H), 7.47(d, J=7.5Hz, 1H), 7.35( s,1H),7.28–7.18(m,3H),7.14(t,J=7.2Hz,1H),7.07(d,J=8.4Hz,1H),7.00–6.88(m,2H),3.81(d ,J=14.0Hz,1H),3.47(d,J=14.0Hz,1H),2.25(s,3H); 13 C NMR (101MHz, CDCl 3 )δ202.27,159.44,157.98,147.53,139.12,139.07,136.56,129.75,128.88,128.65,128.42,127.79,127.45,126.98,126.38,125.91,124.69,123.15,120.00,113.17,72.01,46.26,20.70。

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Abstract

The invention discloses 2, 2-disubstituted indoline-3-ketone alkaloid as well as a preparation method and application thereof, and belongs to the field of medicinal chemistry. The structural general formula of the 2, 2-disubstituted indoline-3-ketone alkaloid is as shown in (1), R1 is a hydrogen atom, a halogen atom, alkyl with 1-4 carbon atoms and alkoxy with 1-4 carbon atoms, and the position of R1 is monosubstituted from the 4-position to the 7-position of a benzene ring; R2 is alkyl or ester group with 1-4 carbon atoms, siloxy, halogen substituted alkyl, phenyl, various substituted phenyl, furyl, thienyl or pyridyl; R3 can be hydrogen, halogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, alkoxycarbonyl with 1-4 carbon atoms, trifluoromethyl and phenyl, and the position of R3 is monosubstituted at 5-8 positions of a quinoline ring. The compound has good activity in the antibacterial aspect, and can be used for preparing medicines for treating bacterial infection by taking the compound as an effective component. (1).

Description

technical field [0001] The invention relates to a 2,2-disubstituted indolin-3-one alkaloid, its green synthetic preparation and its use in the preparation of antibacterial infection drugs, belonging to the field of medicinal chemistry. Background technique [0002] Bacterial infection is a common clinical disease. In the past ten to twenty years, due to the overuse and misuse of antibiotics, drug resistance has frequently emerged and spread rapidly, especially the emergence of multi-drug resistant bacteria has become an important reason for the failure of clinical anti-infective treatment. reason. With the emergence of strains resistant to the latest types of antibacterial agents such as colistin, daptomycin, and carbapenem, at present, only a combination of multiple antibiotics can be used to treat drug-resistant bacterial infections clinically. However, the dosage and number of medications are gradually increasing. Therefore, it is of great significance to develop antibac...

Claims

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Application Information

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IPC IPC(8): C07D401/06C07D409/14A61P31/04
CPCC07D401/06C07D409/14A61P31/04Y02A50/30
Inventor 谢智宇许志红张占涛方万航吴增龙傅一帆
Owner XUCHANG UNIV
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