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Indole[3,2-c]quinoline compounds or pharmaceutically acceptable salts thereof, and preparation method and application thereof

A compound, 2-c technology, applied in organic chemistry, pharmaceutical formulations, medical preparations containing active ingredients, etc., can solve the problems of inappropriate production practice and application, single substrate applicability, harsh reaction conditions, etc. Important academic value and practical industrial application and promotion significance, the effect of good functional group tolerance and simple catalytic system

Inactive Publication Date: 2014-02-05
GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many methods for synthesizing such compounds reported in the literature have disadvantages of varying degrees, such as long reaction steps, difficult access to substrates, low yields, harsh reaction conditions, relatively single applicability of substrates, and poor reaction reproducibility. etc., not suitable for production practice and application

Method used

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  • Indole[3,2-c]quinoline compounds or pharmaceutically acceptable salts thereof, and preparation method and application thereof
  • Indole[3,2-c]quinoline compounds or pharmaceutically acceptable salts thereof, and preparation method and application thereof
  • Indole[3,2-c]quinoline compounds or pharmaceutically acceptable salts thereof, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of embodiment 1 compound ZQ0424

[0033] 1. Preparation of intermediate product (1): under the protection of Ar, 2-iodoaniline (1.0g, 4.6mmol), dichlorobistriphenylphosphine palladium (0.5mol%) and cuprous iodide (1.0mol%) Dissolve in dimethylformamide (4 mL), then inject trimethylsilylacetylene (1.5 equiv.) and diethylamine (8.0 equiv.), and heat the reaction solution to 50°C. After overnight reaction, water was added to the system and extracted twice with ethyl acetate. The organic phases were combined, washed twice with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed on a rotary evaporator, and the residue was separated by column chromatography to obtain the intermediate product (1) with a yield of 96%.

[0034] 2. Preparation of the intermediate product (2): Dissolve the intermediate product (1) (1.0 g) obtained in the above step 1 in methanol, add potassium carbonate (2.0 equiv.) to the reaction system, and react a...

Embodiment 2

[0040] The preparation of embodiment 2 compound ZQ0425

[0041] Prepared according to the method of compound ZQ0424, the substrate and corresponding aldehyde added in the reaction are shown in Table 1, and its characterization data are: 1 H NMR (400MHz, DMSO-d 6 ):δ12.72(s,1H),8.50(d,J=8.0Hz,1H),8.17(d,J=8.0Hz,1H),8.07(d,J=8.4Hz,1H),7.68-7.75 (m,2H),7.62(t,J=8.0Hz,1H),7.50(t,J=7.6Hz,1H),7.34-7.38(t,J=7.6Hz,1H),3.41-3.46(q, J=7.2Hz, 2H), 1.46-1.49(t, J=7.2Hz, 3H).

[0042] 13 C NMR (100MHz, DMSO-d 6 ): δ159.40, 145.39, 140.67, 139.28, 129.35, 128.45, 125.40, 125.33, 122.26, 122.23, 122.02, 121.16, 116.76, 112.64, 112.30, 30.74, 12.71.

[0043]

Embodiment 3

[0044] The preparation of embodiment 3 compound ZQ0432

[0045] Prepared according to the method of compound ZQ0424, the substrate and corresponding aldehyde added in the reaction are shown in Table 1, and its characterization data are: 1 H NMR (400MHz, DMSO-d 6 ):δ12.71(s,1H),8.50(d,J=8.0Hz,1H),8.20(d,J=7.6Hz,1H),8.05(d,J=8.4Hz,1H),7.68-7.74 (m,2H),7.62(t,J=6.8Hz,1H),7.50(t,J=8.0Hz,1H),7.35(t,J=7.6Hz,1H).3.07(s,3H).

[0046] 13 C NMR (100MHz, DMSO-d 6 ): δ154.74, 145.45, 140.36, 139.24, 129.16, 128.44, 125.43, 125.29, 122.81, 122.27, 122.00, 121.06, 116.74, 113.43, 112.23, 24.95.

[0047]

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Abstract

The invention discloses indole[3,2-c]quinoline compounds represented by formula I or pharmaceutically acceptable salts thereof, and a preparation method and an application thereof, and belongs to the technical field of the pharmaceutical chemistry. The indole[3,2-c]quinoline compounds or pharmaceutically acceptable salts thereof have a very good tubercle bacillus resisting activity, and the MIC value of the most compounds is 2.5mug / mL.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to an indole [3,2-c] quinoline compound or a pharmaceutically acceptable salt thereof, a preparation method and application thereof. Background technique [0002] Tuberculosis is a chronic respiratory infectious disease caused by Mycobacterium tuberculosis complex (Mycobacterium tuberculosis complex, referred to as Mycobacterium tuberculosis), which can affect multiple organ systems throughout the body. The most common site of disease is the lungs, accounting for 80-90% of the total number of tuberculosis in various organs. However, in addition to the lungs, organs such as the liver, kidney, brain, and lymph nodes are also affected. It is mainly transmitted through the respiratory tract, digestive tract, skin and uterus, but the most important route is through the respiratory tract. After the sputum of tuberculosis patients with expelling bacteria is dried, the bacteria...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D471/14A61K31/4745A61P31/06
CPCC07D471/04C07D471/14
Inventor 朱强张天宇刘兰英鲁明辉毛婷婷黄金波
Owner GUANGZHOU INST OF BIOMEDICINE & HEALTH CHINESE ACAD OF SCI
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