3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton, and synthesis method and application thereof

A technology of hydroxybenzoyl and a synthesis method is applied in the field of 3,4-dihydro-3--2-quinolinone biologically active skeleton and its synthesis, and can solve the problems of restricting the application, restricting the industrialization of pharmaceutical production enterprises, and the like, Achieve the effect of good substrate universality, good practical significance and application value, and mild reaction conditions

Active Publication Date: 2019-08-20
QINGDAO AGRI UNIV
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Problems solved by technology

[0010] Although the above reactions can efficiently synthesize 3,4-dihydro-2(1H)-quinolinone skeletons, expensive metal catalysts or high temperat

Method used

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  • 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton, and synthesis method and application thereof
  • 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton, and synthesis method and application thereof
  • 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton, and synthesis method and application thereof

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Embodiment 1

[0043] 1. This embodiment provides a method for synthesizing the bioactive skeleton of 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone, which comprises the following steps:

[0044] Take 0.1 mmol of N-diethyl-substituted o-aminobenzaldehyde compounds in a reaction flask, add 1 mL of solvent in sequence, add 0.12 mmol of 4-hydroxycoumarin, and finally add the catalyst. Control the reaction temperature of the system, keep stirring, trace the reaction by spotting samples on the thin-layer chromatographic plate until the reaction of the raw materials is complete. After the reaction is completed, a silica gel column is used for separation and purification, and the purified product is rotary evaporated to obtain the target product. The reaction formula is as follows:

[0045]

[0046]2. According to the above method, set up 7 parallel test groups, using different catalysts and solvents respectively. The catalysts are p-toluenesulfonic acid monohydrate TsOH·H 2 O, triethylam...

Embodiment 2

[0057] Raw materials: N-Dimethyl-substituted anthranilaldehyde, 4-hydroxycoumarin

[0058] Product: Chemical formula: C 17 h 15 NO 3

[0059] Molecular weight: 281.1052

[0060] Structural formula:

[0061] Yield: 80%

[0062] 1 H NMRδ11.96(s,1H),7.80(d,J=7.6Hz,1H),7.49(t,J=7.3Hz,1H),7.32(t,J=7.7Hz,1H),7.19(d, J=7.3Hz, 1H), 7.11–7.03(m, 2H), 7.00(d, J=8.4Hz, 1H), 6.92(t, J=7.6Hz, 1H), 4.63(dd, J=10.4, 6.0 Hz,1H),3.49(dd,J=15.6,10.5Hz,1H),3.42(s,3H),3.10(dd,J=15.7,5.9Hz,1H). 13 C NMR (126MHz, CDCl 3 )δ201.8, 167.3, 162.9, 140.0, 136.8, 130.8, 128.0, 127.9, 124.2, 123.4, 119.4, 119.1, 118.7, 114.9, 48.3, 30.0, 28.7. HRMS (ESI): calcd for C 17 h 15 NO 3 Na[M+Na] + :304.0950,found:304.0948.

Embodiment 3

[0064] Raw materials: N,N-diethyl-6-amino-2-chlorobenzaldehyde, 4-hydroxycoumarin

[0065] Product: Chemical formula: C 18 h 16 ClNO 3

[0066] Molecular weight: 329.0819

[0067] Structural formula:

[0068] Yield: 70%

[0069] 1 H NMR (500MHz, CDCl 3 )δ11.92(s,1H),7.81(dd,J=8.1,1.1Hz,1H),7.53–7.46(m,1H),7.23(t,J=8.2Hz,1H),7.13(d,J =7.8Hz,1H),7.00(d,J=8.4Hz,2H),6.96–6.90(m,1H),4.60(dd,J=10.0,6.2Hz,1H),4.02(tq,J=14.2, 7.2Hz, 2H), 3.50(dd, J=16.4, 10.0Hz, 1H), 3.33(dd, J=16.4, 6.2Hz, 1H), 1.28(t, J=7.1Hz, 3H). 13 C NMR (125MHz, CDCl 3 )δ201.3, 166.0, 162.9, 140.1, 136.9, 133.6, 130.8, 128.3, 124.3, 123.0, 119.3, 119.2, 118.7, 113.4, 47.6, 38.4, 25.6, 12.6. HRMS (ESI): calcd for C 18 h 16 ClNO 3 Na[M+Na] + :352.0711,found:352.0708.

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Abstract

The invention discloses a 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton, and a synthesis method and an application thereof. The structural formula of the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone active skeleton is shown in the description; and in the structural formula, R<1> is any one of a methyl group and an ethyl group, R<2> is one of the hydrogen atom, a methylgroup and halogens, and R<3> is any one of the hydrogen atom and the halogens. The synthesis method of the bioactive skeleton comprises the following steps: mixing an ortho-aminobenzaldehyde compoundwith a 4-hydroxycoumarin compound in a solvent according to a molar ratio of 1:(1-2), and performing a reaction at 70-90 DEG C to obtain the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone compound. The synthesis method is a method for efficiently synthesizing the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone compound in the green ethanol solvent by the one-step reaction without using a catalyst, and realizes a hydrogen transfer reaction in which the natural product molecule 4-hydroxycoumarin participating for the first time in order to synthesize the 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone compound.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a 3,4-dihydro-3-(2-hydroxybenzoyl)-2(1H)-quinolinone biologically active skeleton and its synthesis method and application. Background technique [0002] Quinolinone and its derivatives are a class of important heterocyclic compounds, which have good biological activity and are widely used in the field of medicine. It plays an important role in the treatment of diseases such as Alzheimer's disease. For example, aripiprazole, a new type of atypical antipsychotic, was launched in the United States in 2002 for the treatment of schizophrenia; rebamipide is effective in promoting mucosal tissue regeneration, reducing tissue inflammation, and enhancing mucosal barrier function. Important role, it is a new type of anti-ulcer drug, which was launched in Japan in 1990; Tipifarnib is a new type of anti-tumor drug, which can be used to treat myeloma and other cancers. It has ent...

Claims

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Application Information

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IPC IPC(8): C07D215/227A61P35/00A61P9/10A61P31/06A61P9/00A61P25/08A61P25/18A61P25/28
CPCA61P9/00A61P9/10A61P25/08A61P25/18A61P25/28A61P31/06A61P35/00C07D215/227
Inventor 李帅帅胡方芝王亮徐鲁斌杨晓宇
Owner QINGDAO AGRI UNIV
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