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Bishydrazide structure compound, preparation method and application thereof

A technology of compounds and hydrates, applied in the preparation of hydrazides, active ingredients of heterocyclic compounds, digestive system, etc., can solve problems such as lack of treatment methods and lack of IBD drugs

Active Publication Date: 2021-05-11
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is currently no suitable treatment
The application of immunosuppressants and anticytokines has improved the relapse rate of IBD patients, but there is still a lack of drugs that can cure IBD

Method used

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  • Bishydrazide structure compound, preparation method and application thereof
  • Bishydrazide structure compound, preparation method and application thereof
  • Bishydrazide structure compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0167] Example 1 Compound A 1 Synthesis:

[0168]

[0169] Step 1: Dissolve compound 1 (500 mg) in DCM (10 mL), cool down to 0°C, add compound 3 (348 mg), slowly warm up to room temperature, and keep at room temperature for 30 minutes. The reaction was quenched by adding water, extracted with ethyl acetate, concentrated under reduced pressure, and the residue was purified by column chromatography using petroleum ether: ethyl acetate = 5:1 as eluent to obtain compound 2 (610 mg, yield 84%). 1 HNMR (400MHz, CDCl3): δ8.00(d, J=8.8Hz, 2H), 7.60(d, J=8.8Hz, 2H), 3.90(s, 3H), 1.53(m, 1H), 1.12(m ,2H),0.88(m,2H).

[0170] Step 2: Dissolve compound 2 (400 mg) in CH3CH2OH (25 mL), add hydrazine hydrate (5 mL), and reflux for 4 h. After the reaction was completed, it was concentrated under reduced pressure, and the solid was washed with ice water, and then recrystallized from ethanol to obtain compound 4 (120 mg, yield 40%). 1 HNMR (400MHz, CD3OD): δ7.74(d, J=9.2Hz, 2H), 7.65(d, ...

Embodiment 2

[0172] Example 2 Compound A 2 Synthesis

[0173]

[0174] Compound A 1 (100mg) and K 2 CO 3 (74mg) was dissolved in DMF (2mL), CH was added dropwise under stirring 3 I, continue stirring overnight. After the reaction was completed, the reaction was quenched with water, extracted with EA, dried with anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography with petroleum ether: ethyl acetate = 5: 1 eluent to obtain compound A 2 (90 mg, 85% yield). 1 H NMR (400MHz, DMSO-d 6 ):δ10.37(s,1H),7.57(d,J=8.8Hz,1H),7.20(d,J=8.8Hz,1H),3.12(s,3H),2.94(s,1H),1.75 (m,1H),1.45(m,3H),1.19(m,2H),0.88(m,4H),0.79(d,J=5.6Hz,4H).LRMS(ESI):387.0(M) + .

Embodiment 3-37

[0175] Example 3-37 Compound A 3 -A 37 Synthesis

[0176] With reference to the method of Example 1-2, the substrate in Example 1 was replaced with the corresponding substrate, thereby synthesizing Compound A 3 -A 37 .

[0177] The structures and characterization results of compounds A3-A37 are as follows:

[0178] Table A

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

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Abstract

The invention provides a bishydrazide structure compound, a preparation method and application thereof, specifically a bishydrazide structure compound as shown in a formula I, wherein the compound has the effects of enhancing the activity of intestinal stem cells, promoting the repair of intestinal epithelium and reducing the expression of proinflammatory cytokines so as to treat inflammatory intestinal diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to bishydrazide structural compounds, a preparation method and application thereof. Background technique [0002] Inflammatory bowel disease (IBD), including ulcerative colitis (UC) and Crohn's disease (CD), is characterized by recurrent inflammation of the digestive tract. In recent years, the global incidence rate has increased significantly. The pathogenesis of IBD is not yet clear, and studies have shown that it is related to factors such as heredity, immunity, infection and mental activity. Recurrent disease can cause DNA damage and microsatellite instability in mucosal cells, leading to colon cancer. Studies have confirmed that the risk of colon cancer in IBD patients is significantly higher than that of normal people. [0003] Among the inflammatory cytokines involved in the pathogenesis of IBD, members of the IL-12 family, especially IL-23, have received exte...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C243/32C07C241/04C07D263/32C07D213/82A61K31/195A61K31/4164A61K31/44A61P29/00A61P1/00
CPCC07C243/32C07D263/32C07D213/82A61P29/00A61P1/00C07C2601/02C07C2601/14A61K31/195A61K31/4164A61K31/44C07C241/04C07D213/87C07C243/38A61K31/166
Inventor 蒋华良沈晓燕郑明月侯辉鲍维廉刘小红张素林杨瑞瑞吴小龙
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI