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Pyridopyrazolo cinnoline compound, preparation method and application thereof

A technology for pyridopyrazole and compound, which is applied in the field of pyridopyrazolocinnoline compounds and their preparation, can solve the problems of increase, the research lag of compound functionality, etc., and achieves good antibacterial activity, good substrate generalization The effect of adaptability and simple preparation method

Pending Publication Date: 2020-11-06
朱继强
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The research on the synthesis of a series of cinnoline compounds with new structures by new methods is developing rapidly, but the research on the functionality of these compounds is relatively lagging behind. Therefore, it is not only necessary to develop a simple, efficient, economical, selective and tolerant There are good ways to synthesize cinnoline compounds and their derivatives, and there is an increasing demand for in-depth research on their functionality

Method used

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  • Pyridopyrazolo cinnoline compound, preparation method and application thereof
  • Pyridopyrazolo cinnoline compound, preparation method and application thereof
  • Pyridopyrazolo cinnoline compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of compound 4aa:

[0063] Add 1mmol of 1-phenyl-2-vinylpyrazolidin-3-one and 1.2mmol of 1-(3-aminopyrazin-2-yl)ethanone into the reaction flask, vacuumize and change nitrogen, and Add 0.01mmol of [Cp*RhCl under nitrogen protection 2 ] 2 , 0.2 mmol of Pd(OAc) 2 And 3.0mmol of AcOH, finally add 5mL of anhydrous xylene, put it in an oil bath at 100°C and heat it for 18h, TLC detects that the reaction is complete, the reaction solution is cooled to room temperature, filtered with diatomaceous earth, washed with ethyl acetate, and the solution is depressurized After concentration, it was separated by silica gel column chromatography, and the developer used ethyl acetate:n-hexane=1:5 to obtain the target compound as a light yellow solid. The structural formula and characterization are as follows:

[0064]

[0065] 13-Methyl-5,6-dihydro-14H-pyrazino[2",3":5',6']pyrido[2',3':3,4]pyrazolo[1,2 -a] cinnoline; 1 H NMR (400MHz, CDCl 3 )δ8.60(m, 2H), 7.19(d, J=9....

Embodiment 2

[0067] Preparation of compound 4ba: specific experimental operation process with reference to Example 1, 1-phenyl-2-vinylpyrazolidin-3-one of 1mmol, 1-(3-amino-6-methylpyrazine of 1.2mmol -2-yl) ethyl ketone was added in the reaction flask, vacuumed for nitrogen, and 0.01 mmol of [Cp*RhCl was added under nitrogen protection 2 ] 2 , 0.2 mmol of Pd(OAc) 2 And 3.0mmol of AcOH, finally add 5mL of anhydrous xylene, put it in a 100°C oil bath and heat for 18h, the product obtained is a light yellow oily liquid, the product structure and characterization are as follows:

[0068]

[0069] 11,13-Dimethyl-5,6-dihydro-14H-pyrazino[2",3":5',6']pyrido[2',3':3,4]pyrazolo[ 1,2-a]cinnoline; 1 H NMR (400MHz, CDCl 3)δ8.57(s,1H),7.12–7.03(m,2H),6.76(t,J=11.2Hz,1H),6.58(d,J=7.3Hz,1H),4.35(s,2H), 3.39(m,2H),3.09(m,2H),2.68(s,3H),2.59(s,3H). 13 C NMR (101MHz, CDCl 3 )δ160.31, 151.65, 149.03, 148.92, 144.50, 144.05, 138.12, 129.95, 127.07, 121.84, 120.33, 116.90, 116.47, 56.35, 47.70, 26.0...

Embodiment 3

[0071] Preparation of compound 4ca: specific experimental operation process with reference to Example 1, 1mmol of 1-phenyl-2-vinylpyrazolidin-3-one, 1.2mmol of 1-(3-amino-6-chloropyrazine- 2-yl) ethyl ketone was added in the reaction flask, vacuumed for nitrogen, and 0.01 mmol of [Cp*RhCl was added under nitrogen protection 2 ] 2 , 0.2 mmol of Pd(OAc) 2 And 3.0mmol of AcOH, finally add 5mL of anhydrous xylene, put it in a 100°C oil bath and heat it for 18h, the product obtained is a light yellow solid, the structural formula and characterization of the product are as follows:

[0072]

[0073] 11-Chloro-13-methyl-5,6-dihydro-14H-pyrazino[2",3":5',6']pyrido[2',3':3,4]pyrazolo [1,2-a]cinnoline; 1 H NMR (400MHz, CDCl 3 )δ8.81(s,1H),7.07–6.99(m,2H),6.73(t,J=8.4Hz,1H),6.55(d,J=7.4,1H),4.32(s,2H),3.76 (m,2H),3.39(m,2H),2.49(s,3H). 13 C NMR (101MHz, CDCl 3 )δ159.87, 151.34, 149.55, 146.15, 145.82, 145.68, 141.48, 127.33, 126.35, 123.04, 122.88, 121.24, 117.45, 57.40, 49.08,...

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Abstract

The invention provides a pyridopyrazolo cinnoline compound and a preparation method thereof. According to the invention, the pyridopyrazolo cinnoline compound is prepared from a 1-aryl-2-vinyl pyrazolidone compound and an aminopyrazinone compound through a Friedlander reaction and an arylhydroalkylation reaction at the same time under the action of a catalyst and an additive; the preparation method is simple, and the compound has good substrate universality; the pyridopyrazolo cinnoline compound provided by the invention is a brand-new synthetic method provided on the basis of the prior art; and the synthesized pyridopyrazolo cinnoline compound has good antibacterial activity on escherichia coli, pseudomonas aeruginosa, staphylococcus aureus and bacillus subtilis, and a new choice is provided for research and clinical use of antibacterial drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a pyridopyrazolocinnoline compound and a preparation method and application thereof. Background technique [0002] Cinnoline compounds have various biological activities such as antibacterial, anticancer, antiviral, anti-inflammatory and sedative, and because the cinnoline ring is also an excellent electron acceptor, the cinnoline skeleton has become the dominant skeleton in the research and development of new materials and new drugs. Cinnoline itself is cytotoxic and can inhibit the growth of Escherichia coli strains. Cinnoline derivatives introduced with substituents or ring structures exhibit a wider range of biological activities. There are no natural cinnoline compounds in nature, and the reported cinnoline compounds are all obtained through organic synthesis. However, due to limited synthesis methods, it is far from meeting the demand for efficient synthesis of...

Claims

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Application Information

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IPC IPC(8): C07D471/22A61P31/04
CPCC07D471/22A61P31/04Y02A50/30
Inventor 朱继强
Owner 朱继强
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