Compound having affinity with progeria dementia A beta plaques, preparation method and application thereof

A compound and a dementia technology, which are applied to compounds having affinity with Alzheimer's Aβ plaques, their preparation and application fields, and can solve the problems of harsh synthetic process conditions, low yield, and difficult synthesis, etc.

Inactive Publication Date: 2010-07-14
BEIJING FORESTRY UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This compound can be used in the diagnosis of AD brain, but this type of compound is difficult

Method used

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  • Compound having affinity with progeria dementia A beta plaques, preparation method and application thereof
  • Compound having affinity with progeria dementia A beta plaques, preparation method and application thereof
  • Compound having affinity with progeria dementia A beta plaques, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Example 1 Preparation of N-methyl-4-(3-chlorophenylthio)phthalimide (3-Cl-MSPH)

[0085] Dissolve 1.03 g of N-methyl-4-nitrophthalimide and 5 mmol of 3-chlorothiophenol in 15 mL of N, N-dimethylformamide (DMF), and add 6 mmol anhydrous K 2 CO 3 , stirring at room temperature (25° C.) for 12 hours to perform a coupling reaction;

[0086] Remove K by suction filtration under reduced pressure 2 CO 3 After that, the solvent N, N-dimethylformamide was distilled off under reduced pressure, the residue was dissolved in ethyl acetate, and then water was added for repeated extraction until the water phase was neutral;

[0087] with anhydrous MgSO 4 Dry the ethyl acetate phase, use a rotary evaporator to remove ethyl acetate, and recrystallize the residue with methanol to obtain off-white crystals of N-methyl-4-(3-chlorophenylthio)phthalimide (3- Cl-MSPH), the yield of 3-Cl-MSPH: 51.2%; m.p.135-136 ℃; IR (cm -1 ): 3450, 1714, 1701, 1604, 1438, 735, 680; 1 H NMR (500MHz, C...

Embodiment 2

[0089] Example 2 Preparation of N-methyl-4-(4-chlorophenylthio)phthalimide (4-Cl-MSPH)

[0090] In addition to using 4-chlorothiophenol and N-methyl-4-nitrophthalimide dissolved in dichloromethane, the coupling reaction was carried out under the action of catalyst anhydrous sodium carbonate to obtain off-white crystals Except N-methyl-4-(4-chlorophenylsulfanyl) phthalimide (4-Cl-MSPH), all the other are the same as Example 1, and the productive rate of 4-Cl-MSPH is 60.7% ; m.p. 136-136.5°C. IR (cm -1 ): 3444, 1715, 1706, 1650, 1607, 1435, 737, 501. 1 H NMR (500MHz, CDCl 3 , δppm): 7.69 (1H, d, J=7.8Hz), 7.52 (1H, s), 7.49 (5H, m), 3.15 (3H, s). HRMS: calcd for C 15 h 10 NO 2 SClNa, 326.0018; found: 326.0023; the structural formula is

Embodiment 3

[0091] Example 3 Preparation of N-methyl-4-(3-bromophenylthio)phthalimide (3-Br-MSPH)

[0092] In addition to using 3-bromothiophenol and N-methyl-4-nitrophthalimide dissolved in acetone, the coupling reaction was carried out to obtain light yellow granular crystal N-methyl-4-(3 -Bromophenylthio) phthalimide (3-Br-MSPH), the rest are the same as in Example 1, and the yield of 3-Br-MSPH is 49.1%; m.p.131.5-132°C; IR ( cm -1 ): 3451, 2359, 1715, 1700, 1601, 1436, 736, 676; 1 H NMR (500MHz, CDCl 3 , δppm): 7.67 (1H, d, J = 8.2Hz), 7.64 (1H, s), 7.54 (2H, m), 7.48 (1H, d, J = 7.8Hz), 7.42 (1H, d, J = 7.8Hz), 7.29(1H, d, J=7.9Hz), 3.16(3H, s); HRMS: calcd for C 15 h 10 NO 2 SBr, 347.9694; found: 347.9705;

[0093] The structural formula is

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PUM

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Abstract

The invention provides a compound having affinity with progeria dementia A beta plaques, a preparation method and application thereof in imaging progeria dementia A beta plaques. The structural general formula of the compound of the invention is as follows: wherein R group is positioned in the meta position or pera position of sulfhydryl, and the R group represents Cl, Br, I, CH3, OH, OCH3, NH2, NHCH3 and N(CH3)2. The compound of the invention has high affinity and selectivity with progeria dementia A beta plaques and is a core compound with a novel structure, has low competition binding constant Ki to A beta plaques, can be prepared to a corresponding A beta plaque imaging agent and is used for early diagnosis of progeria dementia.

Description

technical field [0001] The invention relates to the preparation of an AD brain plaque imaging agent with a novel core structure, the biological evaluation of its affinity to Aβ plaques, and its potential application prospect in the diagnosis of Alzheimer's disease. technical background [0002] AD (Alzheimer's disease), also known as Alzheimer's disease, is a primary degenerative brain degenerative disease with an unknown etiology. It is a disease that gradually loses thinking and behavioral abilities due to the degeneration of brain cells, and eventually leads to death. AD brain lesions are mainly manifested as a large number of senile plaques (Senile Plaque, SP) and neurofibrillary tangles (Neurofibrillary tangle, NFT) in the brain, as well as diffuse cerebral atrophy in the cortex, a large number of neurons, and a significant decrease in the content of acetylcholinease and acetylcholine. Wait. [0003] The senile plaques (SPs) formed by the accumulation of β-amyloid (Aβ)...

Claims

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Application Information

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IPC IPC(8): C07D209/48A61K51/04A61K101/02
Inventor 段新红刘伯里
Owner BEIJING FORESTRY UNIVERSITY
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