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Pyrrolopyridine bisamide-containing imidazole compound as well as preparation method and application thereof

A technology of pyrrolopyridine bisamide imidazole and rolopyridine bisamide imidazole, which is applied in the field of organic small molecule drugs, can solve problems such as toxicity problems, and achieve the effect of high anti-inflammatory effect in vivo

Active Publication Date: 2021-12-31
英维沃化工科技(广州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the complexity of IBD, the above drugs are only partially effective and have toxicity issues, so it is still necessary to develop new anti-IBD drugs with high efficacy and safety

Method used

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  • Pyrrolopyridine bisamide-containing imidazole compound as well as preparation method and application thereof
  • Pyrrolopyridine bisamide-containing imidazole compound as well as preparation method and application thereof
  • Pyrrolopyridine bisamide-containing imidazole compound as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1 (synthetic described pyrrolopyridine-containing bisamide imidazole compound)

[0036] Preparation of compound (I)

[0037] S1. Add 3,3-dibromo-1,1,1-trifluoropropan-2-one (1.2mmol) to an aqueous solution of sodium acetate (2.5mmol) and stir at 90°C for 30 minutes to make 3,3 -Dibromo-1,1,1-trifluoropropan-2-one is dissolved in water. Then add 1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1mmol), NH 4 OH (10 mmol) and methanol and stirred overnight to yield crude 3-(4-(trifluoromethyl)-1H-imidazol-2-yl)-1H-pyrrolo[2,3-b]pyridine (interm. 1) Go straight to the next step.

[0038] The chemical reaction formula of above-mentioned step S1. is as follows:

[0039]

[0040] S2. Take step S1. The intermediate 1 crude product (1mmol) that obtains is dissolved in H 2 O / C 2 h 5 OH (1:9, 100 mL), then solid sodium hydroxide (10 mmol) was added, and the resulting mixture was stirred at 90° C. for 2 hours. The mixture was cooled to room temperature and hydrochlori...

Embodiment 2

[0047] Embodiment 2 (anti-inflammatory activity research)

[0048] The in vitro / in vivo anti-inflammatory activity of the compounds of the present invention is demonstrated by the following methods. These effects indicate that compounds of the invention inhibit lipopolysaccharide (LPS)-induced NO production in RAW264.7 macrophages, which stimulates NO release in macrophages and plays an important role in inflammatory conditions. In addition, in vivo animal experiments show that the compound of the present invention can significantly reduce colonic inflammation induced by DSS. The specific test method is as follows:

[0049] (1) Lipopolysaccharide (LPS) stimulates NO release in macrophages, which plays an important role in inflammatory conditions. We therefore evaluated the inhibitory effect of the newly synthesized compound of formula (I) on LPS-induced NO production in RAW264.7 cells. To rule out the possibility that the inhibition of NO production was due to the cytotoxic...

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PUM

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Abstract

The invention discloses a pyrrolopyridine bisamide-containing imidazole compound as well as a preparation method and application thereof. The chemical structure of the pyrrolopyridine bisamide-containing imidazole compound is as shown in a formula (I). The compound has anti-inflammatory activity (inhibiting generation of NO and release of inflammatory cytokines), can effectively inhibit generation of NO in RAW264.7 cells induced by lipopolysaccharide (LPS), shows a relatively high in-vivo anti-inflammatory effect in a mouse model of colitis induced by DSS, and does not have obvious toxicity. The imidazole compound containing pyrrolopyridine bisamide is expected to be used as an efficient and safe novel anti-IBD medicine.

Description

technical field [0001] The invention belongs to the field of organic small molecule drugs, and in particular relates to a pyrrolopyridine-containing bisamide imidazole compound and a preparation method and application thereof. Background technique [0002] Inflammatory bowel disease (Inflammatory Bowel Diseases, IBD) is a type of autoimmune disease that occurs frequently in humans. The clinical manifestations are repeated abdominal pain, diarrhea, abdominal mass, mucus and bloody stool, intestinal obstruction, intestinal perforation, and weight loss. With the rising incidence in western countries, inflammatory bowel disease has become an important disease affecting human health. According to the pathological features and the location of the disease, it can be divided into ulcerative colitis (Ulcerative colitis, UC) and Crohn's disease (Crohn's disease, CD). When intestinal homeostasis is out of balance, intestinal mucosal permeability increases, resulting in impaired intest...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P29/00
CPCC07D471/04A61P29/00Y02A50/30
Inventor 张炯光方丽军
Owner 英维沃化工科技(广州)有限公司