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

A compound, 2-c technology, applied in the direction of organic chemistry, pharmaceutical formulations, medical preparations containing active ingredients, etc., can solve the problems of unsuitable production practice and application, single substrate applicability, poor reaction reproducibility, etc. Achieve important academic value and practical industrial application and promotion significance, good functional group tolerance, and easy operation

Inactive Publication Date: 2016-04-06
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, preparation method and application thereof
  • Indole[3,2-c]quinoline compounds or pharmaceutically acceptable salts thereof, preparation method and application thereof
  • Indole[3,2-c]quinoline compounds or pharmaceutically acceptable salts thereof, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation of compound ZQ0424

[0033] 1. Preparation of intermediate product (1): under the protection of Ar, combine 2-iodoaniline (1.0g, 4.6mmol), dichloroditriphenylphosphine palladium (0.5mol%) and cuprous iodide (1.0mol%) Dissolve in dimethylformamide (4mL), then inject trimethylsilylacetylene (1.5equiv.) and diethylamine (8.0equiv.), and heat the reaction solution to 50°C. After the 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. The residue was separated by column chromatography to obtain the intermediate product (1) with a yield of 96%.

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

Embodiment 2

[0040] Example 2 Preparation of 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. Its characterization data are: 1 HNMR(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 CNMR(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] Example 3 Preparation of compound ZQ0432

[0045] Prepared according to the method of compound ZQ0424, the substrate and the corresponding aldehyde added in the reaction are shown in Table 1. The characterization data are: 1 HNMR(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 = 6.8 Hz, 1H), 7.50 (t, J = 8.0 Hz, 1H), 7.35 (t, J = 7.6 Hz, 1H) 3.07 (s, 3H).

[0046] 13 CNMR(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 present 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, and a preparation method and application thereof. Background technique [0002] Tuberculosis is a chronic respiratory infectious disease caused by Mycobacterium tuberculosiscomples (Mycobacterium tuberculosiscomples, referred to as Mycobacterium tuberculosis live tuberculosis), which can involve multiple organ systems throughout the body. The most common disease site is the lung, which accounts for 80-90% of the total number of tuberculosis in various organs. However, in addition to the lung, it also affects organs such as the liver, kidney, brain, and lymph nodes. It is mainly spread through the respiratory tract, digestive tract, skin and uterus, but the most important route is through the respiratory tract. After the sputum of an excreting tuberculosis patient dries up, the bacter...

Claims

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Application Information

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Patent Type & Authority Patents(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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