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Water-soluble compound for detecting beta-amyloid protein

An amyloid protein and compound technology, which is applied in the directions of preparations, organic chemistry, measuring devices, etc. for in vivo tests, can solve the problems of difficult preparation of water-soluble injections for detecting and diagnosing beta-amyloid, and achieves excellent water solubility. Properties, Effects of Excellent Selective Binding Ability

Pending Publication Date: 2022-05-27
KOREA ATOMIC ENERGY RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to these characteristics, it is difficult to prepare water-soluble injections for the detection and diagnosis of β-amyloid by retinal imaging when existing diagnostic agents are used

Method used

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  • Water-soluble compound for detecting beta-amyloid protein
  • Water-soluble compound for detecting beta-amyloid protein
  • Water-soluble compound for detecting beta-amyloid protein

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Example 1 Synthesis of Compound 1

[0087] Compound 1: (E)-3-(2,4-(Dimethylamino)styryl)-1,1-dimethyl-1H-benzo[e]indol-3-cation-3-yl ) butane-1-sulfonate ion

[0088]

[0089] To synthesize compound 1, compound 7 (43 mg, 0.289 mmol) and compound 8 (100 mg, 0.289 mmol) were dissolved in butanol, and the resultant was refluxed at 130°C for 24 hours. The reaction was concentrated under reduced pressure and then chromatographed (CH 2 Cl 2 :MeOH=5:1) was isolated, and compound 1 was synthesized.

[0090] 1 H NMR (500MHz, MeOH-d 4, δ, ppm): 1.80-1.83 (2H, m), 1.93-1.96 (8H, m), 2.51-2.52 (2H, m), 3.13 (6H, s), 4.60-4.63 (2H, m), 6.85 (2H,d,J=9.0Hz),7.37(1H,d,J=15.5Hz),7.61(1H,t,J=7.0Hz),7.72(1H,t,J=7.0Hz),7.99(1H ,d,J=8.0Hz),8.12(2H,d,J=8.0Hz),8.17(1H,d,J=9.0Hz),8.32(1H,d,J=8.5Hz),8.38(1H,d , J=15.5Hz).

Embodiment 2

[0091] Example 2 Synthesis of Compound 2 and Compound 3

[0092] Compound 2: (E)-4-(2-(2-(5-(4-(dimethylamino)phenyl)thiophen-2-yl)vinyl)-1,1-dimethyl-1H-benzene [e]indol-3-cation-3-yl)butane-1-sulfonate ion

[0093] Compound 3: (E)-4-(2-(2-(5'-(4-(dimethylamino)phenyl)-[2,2'-bithiophene]-5-yl)vinyl)-1 ,1-Dimethyl-1H-benzo[e]indol-3-cation-3-yl)butane-1-sulfonate ion

[0094]

[0095] Compound 11 (167 mg, 0.7 mmol) and Pd (PPh 3 ) 4 (80 mg, 0.07 mmol) dissolved in toluene (10 ml). Compound 9 or 10 (0.7 mmol) was dissolved in EtOH (8 ml), and the resultant was added to the mixture. In addition, adding 2M K 2 CO 3 (2 mL), the resultant was refluxed at 120°C for 5 hours, and then concentrated under reduced pressure. The resulting mixture was separated by chromatography (hexane:ethyl acetate=4:1) to synthesize compound 12 or 13.

[0096] Compound 12 or 13 (0.289 mmol) and compound 8 (100 mg, 0.289 mmol) were dissolved in butanol, and the resultant was refluxed at 130° ...

Embodiment 3

[0099] Example 3 Synthesis of Compound 4

[0100] Compound 4: (E)-4-(1,1-Dimethyl-2-(4-(piperazin-1-yl)styryl)-1H-benzo[e]indole-3-cation -3-yl)butane-1-sulfonate ion

[0101]

[0102] Compound 14 (84 mg, 0.289 mmol) and Compound 8 (100 mg, 0.289 mmol) were dissolved in butanol, and the resultant was refluxed at 130° C. for 24 hours. The reaction was concentrated under reduced pressure and then chromatographed (CH 2 Cl 2 :MeOH=5:1) was isolated, and compound 15 was synthesized. Dissolve compound 15 in CH 2 Cl 4 In the solution, TFA was added, and the mixture was stirred at room temperature for 12 hours to obtain compound 4.

[0103] 1 H NMR (500MHz, MeOH-d 4 ,δ,ppm): 1.82-1.83(2H,m), 1.97-1.99(8H,m), 2.53-2.54(2H,m), 3.22-3.24(2H,m), 3.69-3.71(2H,m) ,4.69-4.72(2H,m),7.12(2H,d,J=9.0Hz),7.53(1H,d,J=15.5Hz),7.65(1H,t,J=7.0Hz),7.75(1H, t,J=7.0Hz),8.05(1H,d,J=8.0Hz),8.15-8.22(4H,m),8.35(1H,d,J=8.5Hz),8.43(1H,d,J=15.5 Hz).

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Abstract

The invention relates to a water-soluble compound for detecting beta-amyloid protein and a preparation method of the water-soluble compound. The compound of the present invention has excellent water solubility, and thus can provide a water-soluble preparation for detecting beta-amyloid protein. Therefore, there is an effect that the compound can be used as a composition for detecting beta-amyloid protein by retinal imaging.

Description

technical field [0001] The present invention relates to a compound for detecting β-amyloid (Aβ) and a preparation method thereof. [0002] In particular, the present invention relates to water-soluble imaging agents and methods for their preparation. Background technique [0003] With the development of modern medicine, the population of elderly people around the world is increasing, and therefore, the number of patients suffering from senile dementia is also increasing rapidly. Alzheimer's disease is the most common form of dementia and is a progressive neurodegenerative disease marked by memory loss, cognitive and behavioral instability. The cause of the disease is unknown, but as a result of analyzing postmortem brain tissue of patients, the accumulation of amyloid plaques composed of beta-amyloid (Aβ) peptides between nerve cells , and neurofibrillary tangles formed by hyperphosphorylated tau fibrils in neural cells have been reported. [0004] 39 to 43 amino acids, i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/60C07D409/06C07D409/14C09K11/06A61K49/00
CPCC07D209/60C07D409/06C07D409/14C09K11/06A61K49/0032C09K2211/1029C09K2211/1092C09K2211/1007C09K2211/1044C07D209/10A61K51/0446G01N33/582G01N33/6896
Inventor 朴龙大田棕豪赵珉镐李东垠
Owner KOREA ATOMIC ENERGY RES INST
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