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Bispiperidine-substituted isoflavone compounds and uses thereof

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

Active Publication Date: 2021-07-20
INST OF MATERIA MEDICA 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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  • Bispiperidine-substituted isoflavone compounds and uses thereof
  • Bispiperidine-substituted isoflavone compounds and uses thereof
  • Bispiperidine-substituted isoflavone compounds and uses thereof

Examples

Experimental program
Comparison scheme
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-necked bottle, add formononetin (5g, 18.6mmol), finely ground anhydrous potassium carbonate powder (30g, 217mmol), 500mL acetone, and then add 1,4-dibromobutane (24mL, 198mmol ), heated to reflux for 10 h, concentrated the reaction mixture under reduced pressure, added water to the residue, stirred, filtered with suction, washed the filter cake with water, and dried to obtain 6.62 g of a 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 / z): 403.31 [M+H]+.

[0042] Synthesi...

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Abstract

The invention discloses a novel bispiperidine-substituted isoflavone compound I that can dose-dependently inhibit the activity of cellular histamine H3 receptors and cellular B- and butyrylcholinesterase activities at a safe dose. This single molecule has Compounds with multi-target activity can protect nerve cells; reduce hypoxic damage to nerve cells; regulate neuroinflammation; have strong inhibitory effects on histamine H3 receptors and B- and butyrylcholinesterase activities; animal experiments have proved that Compound I has low toxicity, can pass through the blood-brain barrier, can significantly improve scopolamine-induced dementia in mice, and can enhance learning and memory functions. Compound I is expected to be a drug for preventing and / or treating learning and memory impairment and Alzheimer's disease, vascular dementia, Parkinson's disease, Huntington's disease and the like.

Description

technical field [0001] The present invention relates to a bispiperidine-substituted isoflavone compound with histamine H3 receptor antagonistic effect, double cholinesterase inhibitory effect, nerve cell protection and anti-inflammatory effect, and the compound is effective in treating 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 etiology of AD is not fully understood, multiple factors play an important role in the pathophysiology of the disease, mainly including loss of synapses, β-amyloid (Aβ) deposition, tau hyperphosphorylation, metal Ion homeostasis, oxidative damage, and neurotransmitter system dysfunction, among others. In the past 30 years, scientists have made some progress in the research of AD treatmen...

Claims

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Application Information

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Patent Type & Authority Patents(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 CHINESE ACAD OF MEDICAL SCI
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