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Synthesis and application of quinoline-2(1H) ketopiperazines compound

A technology of ketone compounds and compounds, applied in the field of medicine

Inactive Publication Date: 2019-03-08
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the novel compounds involved in the present invention have not been reported in terms of inhibiting the activity of chitin synthase, so they can be used as inhibitors of chitin synthase and developed into novel antifungal preparations for human contribute to health

Method used

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  • Synthesis and application of quinoline-2(1H) ketopiperazines compound
  • Synthesis and application of quinoline-2(1H) ketopiperazines compound
  • Synthesis and application of quinoline-2(1H) ketopiperazines compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] 5-(pyrazin-1-yl)-3,4-dihydroquinoline-2(1 H ) ketone (2)

[0032]

[0033] Add 5-amino-3,4-dihydroquinoline-2 (1 H ) ketone 7 (5.00 g, 30.83 mmol), bis-(2-bromoethyl) amine hydrobromide (50.57 g, 33.91 mmol), stirred and warmed up to 80 ° C, and added dropwise three batches of hydroxide within half an hour Potassium (1.90 g, 33.91 mmol, 10 ml) in water. After the addition, the reaction was warming up to 100 ° C, and then incubated for 3 hours. After the reaction was completed, it was cooled to room temperature, filtered, and the filtrate was adjusted to a pH of 10 with 10% potassium hydroxide aqueous solution, and a large amount of white solids were separated out. Suction filtration, washing with an appropriate amount of water, and drying gave white powdery solid 8 (6.4 g, yield 61%, Mp 235-237 °C); 1 H NMR (300 MHz, DMSO-d 6 ) δ: 10.01 (s, 1H, quinolin, -CONH-), 7.07(t, J = 7.9 Hz, 1H, quinolin-H 7 ), 6.65 (d, J = 8.0 Hz, 1H, quinolin-H 8 ), 6.58(d, J =...

Embodiment 2

[0035] 5-(4-(oxirane-2-yl-methyl)pyrazin-1-yl)-3,4-dihydroquinoline-2(1 H ) ketone (3)

[0036]

[0037] Add 5-(pyrazin-1-yl)-3,4-dihydroquinoline-2(1 H) ketone 8 (6.2 g, 29.07 mmol), potassium iodide (0.12 g, 0.73 mmol), tetra-tert-butylammonium bromide (0.24 g, 0.73 mmol), stirred at room temperature until completely dissolved, then added epichlorohydrin (5.38 g , 58.14 mmol), after stirring for about 10 minutes, a white colloidal solid was precipitated. Stir the reaction at room temperature for 4 hours. After the reaction is complete, a creamy white solid sinks in the bottom of the bottle. Remove the upper aqueous layer, add ethyl acetate to crystallize, filter, and dry to obtain white powdery solid 9 (5.3 g, yield 64%, Mp 184-186 °C); 1 H NMR (300 MHz, DMSO-d 6 ) δ: 10.02 (s, 1H, quinolin,-CONH-), 7.08 (t, J = 7.9 Hz, 1H, quinolin-H 7 ), 6.69 (d, J = 7.9 Hz, 1H, quinolin-H 8 ), 6.60 (d, J = 7.8 Hz, 1H, quinolin-H 6 ), 3.05 (m, 1H, CH), 2.76-2.87 (m, 6H, -CH...

Embodiment 3

[0039] 5-(4-(2-Hydroxy-3-((4-methoxyphenyl)amino)propyl)piperazin-1-yl)-2-oxo-1,2,3,4-tetrahydroquinone Phenyl hydrochloride (1a)

[0040]

[0041] 5-(4-(oxirane-2-yl-methyl)pyrazin-1-yl)-3,4-dihydroquinoline-2(1 H ) ketone 9 (0.20 g, 0.7 mmol) and p-methoxyaniline (0.17 g, 1.4 mmol) were mixed uniformly and then heated to 90 °C until the reaction was molten, and stirred for 0.5 hours. Cooled and passed through the column to obtain a colorless oily liquid. After the oil was acidified with concentrated hydrochloric acid, it was recrystallized from a methanol-acetone mixed solvent to obtain 10a as a white powdery solid (yield 75%, Mp 258-261 °C); 1 H NMR (300 MHz, CDCl 3 ) δ: 7.99 (s, 1H, quinolin, -CONH-), 7.17 (t, J = 7.9 Hz, 1H, quinolin-H 7 ), 6.80(m, 3H, quinolin-H 8 and Ar-H 2 , H 6 ), 6.65 (d, J = 8.8 Hz, 2H, Ar-H 3 , H 5 ), 6.55(d, J = 7.8 Hz, 1H, quinolin-H 6 ), 4.05 (m, 1H, NH), 3.77 (s, 3H, CH 3 O-), 3.17-3.34 (m, 1H, CH), 2.78-3.14 (m, 10H, -CH ...

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Abstract

The invention discloses design synthesis of a novel quinoline-2(1H) ketopiperazines compound and application thereof in the aspect of resisting microorganisms. The structure of the compound is shown in general formula I as shown in the description, and R1 and R2 groups are separately hydrogen, straight-chain or branched-chain alkyl consisting of 1-5 carbon atoms, cycloalkyl and heterocyclyl consisting of 3-8 carbon atoms and aryl; or the R1 and R2 groups and N atoms form 5-8-membered heterocycle or heteroaromatic ring and the like. Through biological activity test experiments on the synthesized compound, it proves that part of the compound has obvious inhibition activity to chitin synthetase, part of the compound has good inhibition activity to candida albicans, aspergillus flavus, novel cryptococcus neoformans and aspergillus fumigatus, and thus, the quinoline-2(1H) ketopiperazines compound can be used for preparing a drug for resisting pathogenic microorganisms.

Description

technical field [0001] The invention belongs to the field of medicine and relates to novel quinoline-2(1 H ) Design and synthesis of ketopiperazine compounds and their application in antimicrobial. Background technique [0002] Since quinolone compounds have excellent antibacterial activity, thousands of quinolone derivatives have been synthesized. Quinolones, part of the quinoline alkaloid family, are an important class of heterocyclic compounds, representing a class of compounds with broad-spectrum biological activities, such as in anticancer, antibacterial, antifungal, antimalarial, antiviral ] etc. Impressive. Quinoline-2-(1 H ) The structure of ketones exists in many synthetic compounds and natural products, and has a wide range of pharmaceutical activities. [0003] Piperazine and its substituted derivatives are one of the more successful pharmacological fragments, which has been proved by the drugs currently used clinically. Usually, compounds with piperazine moie...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/38C07D405/12A61P31/04A61P31/10
CPCA61P31/04A61P31/10C07D215/38C07D405/12Y02A50/30
Inventor 吉庆刚邓乔
Owner SOUTHWEST UNIV
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