Bipiperidine substituted isoflavone compound and uses thereof

A technology of compound and composition, applied in the field of isoflavone compounds substituted by bispiperidine

Active Publication Date: 2019-04-23
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, recent studies have found that BuChE can not only replace AChE to hydrolyze Ach, but also play a role in the process of AD, but the compound inhibiting BuChE too strongly will bring more side effects

Method used

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  • Bipiperidine substituted isoflavone compound and uses thereof
  • Bipiperidine substituted isoflavone compound and uses thereof
  • Bipiperidine substituted isoflavone compound and uses thereof

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Experimental program
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Effect test

Embodiment Construction

[0039] 1. Preparation of Compound I

[0040] Synthesis of 3-(4-methoxyphenyl)-7-(4-bromobutoxy)-4H-chromogen-4-one (2)

[0041] In a 1000mL single-mouth flask, add formononetin (5g, 18.6mmol), finely ground anhydrous potassium carbonate powder (30g, 217mmol), 500mL acetone, and then add 1,4-dibromobutane (24mL, 198mmol) ), the reaction mixture was heated under reflux for 10 hours, the reaction mixture was concentrated under reduced pressure, the residue was added with water, stirred, and filtered with suction. The filter cake was washed with water and dried to obtain 6.62 g of white solid with a yield of 88.6%. mp: 152.8-154.0°C. 1H NMR (400MHz, CDCl3) δ: 8.21 (d, J = 8.8Hz, 1H), 7.91 (s, 1H), 7.50 (d, J = 8.8Hz, 2H), 6.99-6.96 (m, 3H), 6.84 (d,J=2.4Hz,1H),4.10(t,J=6.0Hz,2H),3.84(s,3H),3.51(t,J=6.0Hz,2H),2.14-1.98(m,4H) ; 13C NMR (100MHz, CDCl3) δ: 175.8, 163.2, 159.6, 157.9, 152.0, 130.1, 127.8, 124.9, 124.2, 118.5, 114.7, 114.0, 100.6, 67.6, 55.3, 33.2, 29.3, 27.6. ESI-MS ( m...

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Abstract

The present invention discloses a novel bipiperidine substituted isoflavone compound I, which can inhibit the activity of cell histamine H3 receptors and the activity of cell acetylcholine esterase and cell butyrylcholinesterase in a dose-dependent manner at a safe dose, wherein the single-molecule compound with multi-target activity can protect nerve cells, reduce nerve cell hypoxia injury and regulate neuroinflammation, and has strong inhibition effects on the activities of cell histamine H3 receptors, acetylcholine esterase and butyrylcholinesterase. According to the present invention, theresults of animal experiments show that the compound I has low toxicity, can pass through the blood-brain barrier, can significantly improve scopolamine induced mouse dementia and enhance learning andmemory function, and is expected to be drugs for prevention and/or treatment of learning and memory disorders, Alzheimer's disease, vascular dementia, Parkinson's disease, Huntington's disease and the like. The formula I is defined in the specification.

Description

Technical field [0001] The present invention relates to a bispiperidine substituted isoflavone compound with histamine H3 receptor antagonistic effect, dual cholinesterase inhibitory effect, neuronal protective effect, and anti-inflammatory effect, and the compound is used in the treatment of learning and memory disorders and senile dementia, Application in vascular dementia. It belongs to the field of medical technology. Background technique [0002] Alzheimer's disease (AD) is the most common form of dementia characterized by progressive memory loss and cognitive impairment. Although the exact cause of AD is not fully understood, there are many factors that play an important role in the pathophysiology of the disease, including loss of nerve synapses, β-amyloid (Aβ) deposition, tau protein hyperphosphorylation, and metal Ion homeostasis, oxidative damage and neurotransmitter system dysfunction, etc. In the past 30 years, scientists have made some progress in the research of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/36A61K31/4545A61P25/28A61P25/16A61P25/14A61P25/00A61P29/00A61P39/06
CPCC07D311/36
Inventor 张天泰吴松王冬梅胡敏
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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