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Dihydrazone compound high in affinity with Abeta protein and Tau protein, derivative thereof, and applications of dihydrazone compound and derivative

An amide compound and compound technology, which is applied in the field of medical imaging, can solve the problems of low signal-to-noise ratio, poor in vivo stability, unable to be practically applied, slow removal speed, etc., and achieves high specificity, good pharmacokinetic properties, and rapidity. clear effect

Active Publication Date: 2019-05-03
BEIJING NORMAL UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2-Phenylimidazopyridine derivatives[ 123 I] IMPY (Zhang, Z.P.et al.Journal of Medicinal Chemistry.2003,46:237-243) is the first SPECT imaging agent to enter the clinical stage, but it cannot be practically applied due to its poor stability in vivo
Among these probes [ 18 F]T807 conducted the most in-depth study of AD cases, although [ 18 F]T807 has high selectivity for tau protein, but the latest research found that it has slow clearance in the brain and widespread non-specific binding, resulting in low signal-to-noise ratio

Method used

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  • Dihydrazone compound high in affinity with Abeta protein and Tau protein, derivative thereof, and applications of dihydrazone compound and derivative
  • Dihydrazone compound high in affinity with Abeta protein and Tau protein, derivative thereof, and applications of dihydrazone compound and derivative
  • Dihydrazone compound high in affinity with Abeta protein and Tau protein, derivative thereof, and applications of dihydrazone compound and derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: synthetic compound 1

[0030]

[0031] The compound benzaldehyde (212.4mg, 2.0mmol) was dissolved in 10mL ethanol in a 50mL round bottom flask, then hydrazine hydrate (58.9mg, 1.0mmol) was slowly added to the reaction flask, and the reaction was refluxed at 90°C for 10 minutes. After the reaction was completed, , cooled until a yellow solid precipitated, the precipitated product was suction filtered, and washed with 10 mL of ethanol and petroleum ether, and the crystalline product obtained by suction filtration was dried to obtain 44.0 mg of compound 1, with a yield of 18.5%, and the structure is as follows : 1 H NMR (400MHz, CDCl 3 )δ8.68 (s, 2H), 7.86 (dd, J=6.5, 3.0Hz, 4H), 7.56–7.35 (m, 6H).

Embodiment 2

[0032] Embodiment 2: synthetic compound 2

[0033]

[0034] Compound 2 was prepared from p-fluorobenzaldehyde according to the method for synthesizing compound 1, and 190.0 mg of a milky white solid was obtained with a yield of 77.8%. The structure is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.62(s,2H),7.90–7.74(m,4H),7.21–7.06(m,4H).

Embodiment 3

[0035] Embodiment 3: synthetic compound 3

[0036]

[0037] Compound 3 was prepared from 4-chlorobenzaldehyde according to the method for synthesizing compound 1, and 131.0 mg of light yellow crystalline solid was obtained with a yield of 47.3%. The structure was as follows: 1 H NMR (400MHz, CDCl 3 )δ8.61(s,2H),7.78(d,J=8.5Hz,4H),7.43(d,J=8.5Hz,4H).

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Abstract

The invention provides a dihydrazone compound high in affinity with Abeta protein and Tau protein, a derivative thereof, and applications of the dihydrazone compound and the derivative. The structureof the dihydrazone compound is represented by formula I. The dihydrazone compound can be directly taken as a fluorescence probe used for detecting neurofibrillary tangles in vivo or in tissue samples;when the dihydrazone compound is adopted in nuclear medicine imaging, appropriate radioisotopes are needed for labeling. The dihydrazone compound is especially suitable to be used for diagnosis of neurodegenerative diseases, and diagnosis of patients with diseases with Abeta plaques including Alzheimer's disease.

Description

Technical field [0001] The present invention relates to the field of medical imaging technology, specifically to a dihydrazone compound with high affinity to Aβ protein and Tau protein and its derivatives and applications. Background technique [0002] Alzheimer's disease (AD) is the most common disease in Alzheimer's disease, and its clinical manifestations are mainly caused by progressive memory loss and irreversible impairment of sensory function. It has become the fourth major disease that seriously threatens the health of the elderly after tumors, heart disease, stroke and diabetes. Neuropathological studies of AD have shown that the deposition of extracellular senile plaques (SPs), intracellular neurofibrillary tangles (NFTs) and axonal dystrophies (DNs), which mainly occur in the cortex and hippocampus, are important pathological aspects of AD. feature. Research shows that Aβ protein deposition in the brain begins 5-10 years before the onset of AD. After aggregation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/88C07C249/16C07D295/135C07D213/75C07D213/64A61P25/28A61P25/00C09K11/06G01N21/64G01N1/30
CPCA61P25/28A61P25/00C07C251/88C07D213/64C07D295/135C09K11/06C07D213/74C07D239/42C07D317/58C09K2211/1014C09K2211/1007C07C249/16C07D213/75C07D295/125G01N1/30G01N21/64A61K49/0052A61K51/04A61K51/0455C07C255/66
Inventor 崔孟超周凯翔沈浪涛邓雪松
Owner BEIJING NORMAL UNIVERSITY
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