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Heterocycle compound containing triazole, as well as preparation method and application of heterocycle compound

A technology of heterocycles and compounds, which is applied in the field of triazole-containing heterocycles and their preparation and application, and can solve the problems of poor curative effect of leukemia

Inactive Publication Date: 2016-12-07
TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In order to solve the problem of poor efficacy of drugs used to treat leukemia in the prior art, according to one aspect of the present invention, a triazole-containing heterocyclic compound is provided, and the triazole-containing heterocyclic compound has the following properties: General structural formula:

Method used

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  • Heterocycle compound containing triazole, as well as preparation method and application of heterocycle compound
  • Heterocycle compound containing triazole, as well as preparation method and application of heterocycle compound
  • Heterocycle compound containing triazole, as well as preparation method and application of heterocycle compound

Examples

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Embodiment 1

[0058] Example 1 Chemical Synthesis and Structure Identification of Triazole-containing Heterocyclic Compounds

[0059] 1. The triazole-containing heterocyclic compound provided by the invention has the following general structural formula:

[0060]

[0061] In the above general structural formula, the substituent R includes the following structures:

[0062]

[0063] 2. The chemical synthesis experimental steps of the triazole-containing heterocyclic compounds provided by the present invention

[0064] 2.1 The general synthetic route is:

[0065]

[0066] 2.2 Experimental part

[0067] 2.2.1 Synthesis of compound 4-methyl-2-[(4-pyridin-3-yl-pyrimidin-2-yl)-amino]benzene azide (2)

[0068]

[0069] Take a 100ml three-necked round-bottom flask, and add N-(5-amino-2-methylphenyl)-4-(3-pyridyl)-2-aminopyrimidine (reaction substrate 1, 500mg) in sequence at 0°C , sodium nitrite (250mg), water (15ml) (note that it is best to use mechanical stirring at this time, bec...

example 1-14

[0104] Synthesis of Example 1-14 Compounds 15a-15n

[0105]

example 1

[0106] Synthesis and structure identification of example 1 compound 15a

[0107]

[0108] Get 25ml three-neck round bottom flask, at room temperature, add ethanol-water mixed system (V 乙醇 :V 水 =2:1, 15ml), the obtained compound 5a (0.18g, 0.70mmol), the obtained compound 2 (0.25g, 0.83mmol), then add nano Cu 2 O (0.19g, 1.00mmol), reacted for 12 hours, and monitored the reaction progress by TLC during the reaction. After the reaction was completed, the reaction solution was filtered, concentrated, and purified by silica gel column chromatography to obtain 0.23 g of the product, namely compound 15a. MS of the compound: [M+H] + 554.54; 1 H NMR (400MHz, CDCl 3 )δppm 9.46(m, 1H), 9.12(s, 1H), 8.76-8.74(m, 1H), 8.60(d, J=4.4Hz, 1H), 8.44(d, J=7.2Hz, 2H), 8.30 (s, 1H), 8.16(s, 1H), 7.61(s, 1H), 7.51(d, J=7.2Hz, 2H), 7.41(d, J=8.0Hz, 1H), 7.30(s, 1H) , 7.25(s, 1H), 2.49(s, 3H), 2.36(s, 3H). 13 C NMR (100MHz, CDCl 3 )δ 162.7, 160.0, 159.3, 151.9, 148.6, 145.9, 138.8, 135.4...

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Abstract

The invention provides a heterocycle compound containing triazole, as well as a preparation method and application of the heterocycle compound. The heterocycle compound containing the triazole has a general formula in the following structure (as shown in the description). Cellular level experiments indicate that the heterocycle compound containing the triazole provided by the invention can restrain the proliferation of K562-3d cells, HL60 cells and KG1a cells, and particularly under the situation that the medicine concentration is lower than that of a positive control medicine namely Imatinib, a compound (compound 15c) in an example 3 can also realize the effect of restraining the proliferation of the K562-3d cells, the HL60 cells and the KG1a cells, so that the heterocycle compound containing the triazole provided by the invention can be used for treating leukaemia.

Description

technical field [0001] The invention relates to a triazole-containing heterocyclic compound, a preparation method and application thereof. Background technique [0002] Leukemia, also known as blood cancer, is a kind of clonal malignant disease with abnormal hematopoietic stem cells. The leukemia cells in its clones lose the ability to further differentiate and mature and stagnate at different stages of cell development. In the bone marrow and other hematopoietic tissues, a large number of leukemia cells proliferate and accumulate and infiltrate other organs and tissues, and at the same time inhibit normal hematopoiesis. The clinical manifestations are anemia, bleeding, infection and infiltration of various organs. [0003] Leukemia is usually divided into: 1) acute leukemia; 2) chronic leukemia; 3) special types of leukemia. [0004] Acute leukemia is a clonal malignant disease with abnormal hematopoietic stem cells. The leukemia cells in its clones lose the ability to f...

Claims

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Application Information

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IPC IPC(8): C07D401/14A61K31/506A61P35/02
Inventor 饶子和杨诚陈悦白翠改孙涛潘成文孟凡非李永涛王静晗江银
Owner TIANJIN INT JOINT ACADEMY OF BIOTECH & MEDICINE
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