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A class of 4-((2-substituted quinolin-4-yl) amino) benzoylhydrazine derivatives and its preparation method and application

A technology for benzoylhydrazide and derivatives, which is applied in the field of 4-amino)benzohydrazide derivatives and their preparation, can solve problems such as toxic and side effects, and achieve the effects of low cost, high yield, and mild reaction conditions

Active Publication Date: 2020-11-10
XIAMEN UNIV
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  • Abstract
  • Description
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Problems solved by technology

[0002] Malignant tumors are still one of the major diseases that seriously affect the safety of human life. Although the existing small molecule drugs for the treatment of malignant tumors have certain curative effects, they still have relatively serious side effects

Method used

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  • A class of 4-((2-substituted quinolin-4-yl) amino) benzoylhydrazine derivatives and its preparation method and application
  • A class of 4-((2-substituted quinolin-4-yl) amino) benzoylhydrazine derivatives and its preparation method and application
  • A class of 4-((2-substituted quinolin-4-yl) amino) benzoylhydrazine derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Preparation of N'-((naphthalene-2-yl)methylene)-4-((quinolin-4-yl)amino)phenylhydrazine hydrazide:

[0048]

[0049] Preparation of ethyl 4-((quinolin-4-yl)amino)benzoate:

[0050]

[0051] Add 4-hydroxyquinoline (2.90g, 0.020mol) and phosphorus oxychloride (30mL) into a dry and sealed 100mL reaction bottle, stir the reaction, seal and heat to 120°C to continue the reaction for 3h, TLC detects that the reaction is complete, stop reaction. The reaction solution was cooled to room temperature, concentrated under reduced pressure to remove the solvent, added 50 mL of ice water, decolorized with activated carbon, filtered with suction, collected the filtrate, adjusted the pH to 8-9 with 10% NaOH in an ice bath, and distilled to obtain a colorless liquid 4-chloroquinoline 2.80g, yield 87%.

[0052] In a dry 100mL round bottom flask, add 4-chloroquinoline (1.60g, 0.010mol), ethyl p-aminobenzoate (1.70g, 0.010mol), n-butanol (35mL), 2 drops of concentrated h...

Embodiment 2

[0057] Example 2: 4-((quinolin-4-yl)amino)-N'-((2,3,4-trimethoxyphenyl)methylene)benzohydrazide:

[0058]

[0059] The reaction steps are the same as those in Example 1, except that 2-naphthaldehyde is replaced by 2,3,4-trimethoxybenzaldehyde (21.6mg, 0.11mmol), and finally 24.6mg of a light yellow solid product is obtained by isolation, with a yield of 54% . Spectral data: 1 H NMR (600MHz, DMSO-d6): 11.96(s, 1H), 10.96(br.s., 1H), 8.73(d, J=8.4Hz, 1H), 8.68(s, 1H), 8.64(d, J=6.8Hz, 1H), 8.13(d, J=8.6Hz, 2H), 8.04~8.07(m, 2H), 7.85(ddd, J=2.3, 6.0, 8.4Hz, 1H), 7.61~7.69(m ,3H),7.04(d,J=7.0Hz,1H),6.96(d,J=9.0Hz,1H),3.87(d,J=3.95Hz,6H),3.79(s,3H); 13 C NMR (151MHz, DMSO-d6): 162.4, 159.1, 158.8, 158.6, 155.7, 154.8, 153.1, 144.0, 143.9, 142.0, 140.9, 139.0, 134.5, 132.2, 129.8, 127.8, 125.0, 121.10.9, 12 120.8, 118.0, 116.7, 109.2, 101.0, 62.3, 61.0, 56.5; ESI-MS(+): [M+H] + ,457.5.

Embodiment 3

[0060] Example 3: N'-((4-hydroxy-3-methoxyphenyl)methylene)-4-((quinolin-4-yl)amino)benzohydrazide:

[0061]

[0062] The reaction steps were the same as in Example 1, except that 2-naphthaldehyde was replaced by 4-hydroxy-3 methoxybenzaldehyde (16.7mg, 0.11mmol), and finally 23.0mg of the yellow-white solid product was isolated with a yield of 56%. Spectral data: 1 H NMR (600MHz, DMSO-d 6 ):11.88(s,1H),10.99(br.s.,1H),9.70(br.s.,1H),8.74(d,J=8.4Hz,1H),8.64(d,J=7.0Hz, 1H), 8.39(s, 1H), 8.13(d, J=8.4Hz, 2H), 8.05~8.08(m, 2H), 7.86(ddd, J=2.3, 5.9, 8.3Hz, 1H), 7.67(d ,J=8.4Hz,2H),7.36(d,J=1.5Hz,1H),7.11(dd,J=1.7,8.1Hz,1H),7.04(d,J=7.0Hz,1H),6.9(d ,J=8.07Hz,1H),3.85(s,3H);ESI-MS(+):[M+H] + , 413.4.

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Abstract

The invention relates to 4-((2-substituted quinoline-4-yl)amino)benzoyl hydrazine derivatives as well as a preparation method and application thereof, which relate to N'-substituted methylene-4-((2-substituted quinoline-4-yl)amino)benzoyl hydrazine derivatives. The N'-substituted methylene-4-((2-substituted quinoline-4-group)amino)benzoyl hydrazine derivatives can be applied to the preparation ofan antitumor drug. The invention provides novel derivatives activating a Nur77 signal circuit. The novel derivatives can block the proliferation of tumor cells and induce the cell apoptosis by activating Nur77 related signal circuits, so that the derivatives can be used for treating and preventing various diseases such as malignant tumors, inflammations and the like of the human beings and animals. The derivatives activating the Nur77 signal circuit can be applied to the preparation of drugs for treating and preventing various diseases of the human beings and animals, wherein the diseases comprise malignant tumors, inflammations and the like.

Description

technical field [0001] The present invention relates to N'-substituted methylene-4-((2-substituted quinoline-4-yl) amino) benzoylhydrazine derivatives, especially to a class of 4-((2-substituted quinoline- 4-yl)amino)benzoic hydrazide derivatives and their preparation methods and applications. Background technique [0002] Malignant tumors are still one of the major diseases that seriously affect the safety of human life. Although the existing small molecule drugs for the treatment of malignant tumors have certain curative effects, they still have relatively serious side effects. Therefore, more and more researchers are shifting their targets from traditional cytotoxic drugs to targeted new anti-tumor drugs. [0003] Nuclear receptors (Nuclear Receptors, NRs) superfamily is a large class of functional proteins widely distributed in eukaryotic cell organisms. It is one of the important targets for the potential treatment of malignant tumors. Nur77 (also known as TR3, NGFI-...

Claims

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Application Information

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IPC IPC(8): C07D215/44C07D401/12A61P35/00A61P29/00
CPCA61P29/00A61P35/00C07D215/44C07D401/12
Inventor 刘文吴振方美娟李柏村黄建刚杨沫唐博文李博群王浩杰主父学良
Owner XIAMEN UNIV
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