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Cyanoguanidine derivative, preparation method thereof and anti-tubercle bacillus medicine

A derivative, the technology of cyanoguanidine, applied in the field of materials, can solve the problems of poor curative effect of anti-tuberculosis drugs, and achieve the effect of long-lasting and stable anti-tuberculosis effect, mild conditions, and simple preparation process

Pending Publication Date: 2022-04-12
SHENZHEN BAY LAB +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of this application is to provide a cyanoguanidine derivative and its preparation method, as well as an anti-tuberculosis drug, aiming to solve the problem of poor curative effect of existing anti-tuberculosis drugs to a certain extent

Method used

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  • Cyanoguanidine derivative, preparation method thereof and anti-tubercle bacillus medicine
  • Cyanoguanidine derivative, preparation method thereof and anti-tubercle bacillus medicine
  • Cyanoguanidine derivative, preparation method thereof and anti-tubercle bacillus medicine

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preparation example Construction

[0043] as attached figure 1 As shown, the second aspect of the embodiments of the present application provides a preparation method of a cyanoguanidine derivative, comprising the following preparation steps:

[0044] S10. The 5-nitroindole compound and the benzyl halide compound are subjected to a first substitution reaction under the action of a basic catalyst to obtain a first intermediate;

[0045] S20. the first intermediate is subjected to reduction treatment to obtain the second intermediate;

[0046] S30. the second intermediate and N-cyanocarbonimide diphenyl ester are carried out the second substitution reaction to obtain the third intermediate;

[0047] S40. The third intermediate is subjected to a third substitution reaction with an amine compound to obtain a cyanoguanidine derivative;

[0048] Wherein, the general structural formula of 5-nitroindole compounds is: The general structural formula of benzyl halide compounds is The general structural formula of am...

Embodiment 1

[0081] A sort of A cyanoguanidine derivative (a), the preparation of which comprises the steps:

[0082] ①In a 1000mL round-bottomed flask, add 32.4g (2mmoL) 5-nitroindole and 2mmoL benzyl bromide in sequence 97.7 g (3 mmol) of cesium carbonate and 500 mL of N,N-dimethylformamide, then stirred at 80°C for 12 hours. After the reaction was completed, cooled and filtered, the solution was rotary evaporated under reduced pressure to obtain a solid residue, 200 mL of acetone was added to the residue to dissolve, and finally 300 mL of water was slowly added to the crude product 1, the solid was precipitated, filtered, and dried under reduced pressure to obtain the first intermediate.

[0083] ② The first intermediate (1.5 mmol), iron powder (25 mmol) and ammonium chloride (50 mmol) were added to 50 ml of isopropanol-water (4:1), and the reaction was stirred under reflux at 90° C. for 15 hours. Cool, evaporate the solvent under reduced pressure, add water to the residue to dissol...

Embodiment 2

[0089] A sort of The cyanoguanidine derivative (b), the difference between its preparation and Example 1 is: in step 1, the benzyl bromide compound is White solid 0.30 g; yield 85%.

[0090] The cyanoguanidine derivative (b) 1 H NMR (400MHz, Chloroform-d) δ 7.52(s, 1H), 7.42(d, J=8.0Hz, 2H), 7.25–7.17(m, 2H), 7.15(s, 1H), 7.05(d, J=8.0Hz, 2H), 6.99(d, J=7.9Hz, 1H), 6.56(d, J=3.2Hz, 1H), 5.31(s, 2H), 3.07(s, 1H), 2.63(dq, J=6.8, 3.2 Hz, 1H), 0.86-0.78 (m, 2H), 0.67-0.55 (m, 2H).

[0091] HRMS theoretical value C 22 H 19 N 5 [M+H] + : 354.1214, found: 354.1215.

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Abstract

The invention belongs to the technical field of materials, and particularly relates to a cyanoguanidine derivative, a preparation method thereof and an anti-tubercle bacillus medicine. Wherein the general formula of the chemical structure of the cyano guanidine derivative is shown as a formula I, R1 is selected from one of aryl and heteroaryl, and R2 is selected from one of alkyl, aryl and heteroaryl; r3-R7 are respectively and independently selected from one of hydrogen, halogen, cyano, alkyl, aryl and heteroaryl. The cyanoguanidine derivative provided by the invention has dual mechanisms for inhibiting mycobacterium tuberculosis in a normal growth state, can inhibit the synthesis of mycobacterium tuberculosis protein, and also can inhibit the synthesis of cell wall mycolic acid. The cyanguanidine derivative has an excellent anti-tubercle bacillus effect which is even superior to that of commercially available isoniazide, and the cyanguanidine derivative is not easy to generate drug resistance to most tubercle bacillus.

Description

technical field [0001] The application belongs to the technical field of materials, and in particular relates to a cyanoguanidine derivative, a preparation method thereof, and an anti-tuberculosis drug. Background technique [0002] According to the World Health Organization (WHO), tuberculosis has become the number one deadly infectious disease. my country is one of the countries with a high burden of tuberculosis in the world and one of the countries with the most serious problem of tuberculosis drug resistance. Tuberculosis (Tuberculosis, TB) is caused by its pathogen - Mycobacterium tuberculosis (Mycobacterium tuberculosis) through the air and is a major infectious disease that endangers human health and causes human death. The extensive use of anti-tuberculosis drugs and the mutation of the anti-tuberculosis action site of Mycobacterium tuberculosis have led to the emergence of multi-drug resistant tuberculosis. At present, drug-resistant tuberculosis, especially mult...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C07D401/06C07D409/06A61K31/404A61K31/4439A61P31/06
Inventor 陈杰安黄湧陈学明刘运尹登蒋晨然
Owner SHENZHEN BAY LAB
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