Curcumin analogue and preparation method thereof as well as application of analogue in preparation of Alzheimer disease resisting medicament

A curcumin analogue and reaction technology, which can be used in drug combinations, pharmaceutical formulations, nervous system diseases, etc., can solve problems such as inability to achieve radical cure, achieve good free radical scavenging ability, simple preparation method, and cheap raw materials. Effect

Inactive Publication Date: 2011-10-26
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, drugs developed from a single target can only allevi

Method used

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  • Curcumin analogue and preparation method thereof as well as application of analogue in preparation of Alzheimer disease resisting medicament
  • Curcumin analogue and preparation method thereof as well as application of analogue in preparation of Alzheimer disease resisting medicament
  • Curcumin analogue and preparation method thereof as well as application of analogue in preparation of Alzheimer disease resisting medicament

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment one: the synthesis of compound A1

[0045] At room temperature, dissolve 0.001 mol of 4-(4-methylpiperazine) benzaldehyde and 0.0005 mol of acetone in 1 mL of 95% ethanol and stir evenly, slowly drop about 0.5 mL of 10% NaOH solution into it, and stir at room temperature After about 20 minutes, a large amount of light yellow precipitate precipitated, which was suction filtered, washed with water, and dried to obtain a yellow solid powder, which was recrystallized from ethanol to obtain a light yellow powder, namely compound A1, with a yield of 85%.

[0046]

[0047] Compound A1

[0048] 1 H NMR (400 MHz, CDCl 3 ) δ 7.60 (d, J = 15.8, 2H), 7.43 (t, J = 18.7, 4H), 6.84 (dd, J = 12.0, 8.8, 6H), 3.26 (d, J = 4.6, 8H), 2.44 (d, J = 59.9, 8H), 2.37 (s, 6H); ESI-HRMS m / z : 431.2305 [M+H] + .

Embodiment 2

[0049] Embodiment two: the synthesis of compound A2

[0050] The method is the same as in Example 1, except that cyclopentanone is used instead of acetone to obtain light yellow solid A2 with a yield of 68%.

[0051]

[0052] Compound A2

[0053] 1 H NMR (400 MHz, CDCl 3 ) δ 7.45 (t, J = 9.3, 8H), 6.87 (d, J = 8.8, 4H), 3.30 – 3.23 (m, 8H), 3.00 (s, 4H), 2.54 – 2.46 (m, 8H), 2.29 (s, 6H); ESI-HRMS m / z : 457.2961 [M+H] + .

Embodiment 3

[0054] Embodiment three: the synthesis of compound A3

[0055] The method is the same as in Example 1, except that cyclohexanone is used instead of acetone to obtain light yellow solid A3 with a yield of 61%.

[0056]

[0057] Compound A3

[0058] 1 H NMR (400 MHz, CDCl 3 ) δ 7.67 (s, 2H), 7.36 (d, J = 8.7, 4H), 6.84 (d, J = 8.8, 4H), 3.28-3.18 (m, 8H), 2.85 (t, J = 5.3, 4H), 2.54-2.45 (m, 8H), 2.29 (s, 6H), 1.73 (dd, J = 11.9, 6.1, 2H).ESI-HRMS m / z : 471.3119

[0059] [M+H] + .

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Abstract

The invention belongs to the fields of medicaments and chemical engineering, and discloses a curcumin analogue and a preparation method thereof as well as application of the analogue in the preparation of Alzheimer disease resisting medicament. The structural formula of the curcumin analogue is as shown in the specification, wherein R1 is H, OH, OCH3, or C1-C6 alkyl; R2 is C3-C6 naphthenic base, piperazidine, morpholine, piperidine or oxazoline group and the like; and L is a structure formula as shown in the specification, -CH2NHCH2-, -CH2NH(CH3)CH2-, -CH2NH(CH2CH3)CH2, o/m/p-substituted diacetylbenzene, benzene ring or pyridine and the like, wherein in the structural formula, X is -(CH2)n-, and n is 0-3. The curcumin analogue has an obvious inhibition effect on aggregation of beta-amyloid (A beta), has a strong capability of clearing oxygen radical and simultaneously is capable of chelating divalent metal ions such as ferrous ions (Fe<2+>), copper ions (Cu<2+>) and the like. The curcumin analogue has a wide application prospect in the aspect of preparing Alzheimer disease resisting medicament with multiple target spots.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to a curcumin analogue, a preparation method thereof, and an application thereof in preparation of anti-Alzheimer medicine. Background technique [0002] Alzheimer's disease, also known as early senile dementia, is one of the major diseases that threaten human health and life safety. Epidemiological studies have shown that the incidence of Alzheimer's disease is on the rise as the population ages. Foreign studies have found that among the elderly over 65 years old, the incidence rate of Alzheimer's disease is 5%-10%, and the incidence rate will double every 5 years thereafter. Among the elderly over 85 years old, Alzheimer's disease The incidence rate is as high as 47%-50%. The research and development of anti-Alzheimer's disease drugs has become a focus of attention of chemists and pharmacologists. [0003] Anti-Alzheimer's disease is complex, and the pathogenesis of ...

Claims

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Application Information

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IPC IPC(8): C07D295/112C07D295/02C07D213/68C07D213/38A61K31/496A61K31/4545A61K31/5377A61P25/28
Inventor 黄志纾古练权陈上英谭嘉恒
Owner SUN YAT SEN UNIV
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