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A kind of cemetine analogue, its synthesis method and its application

A technology of wax plum and its analogues, applied in the field of drug synthesis, can solve the problems of no effective prevention and treatment methods, and affect the health of the elderly, and achieve the effects of excellent application prospects, simple structure, and simple process

Active Publication Date: 2021-10-15
JIANGSU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is an important disease that affects the health of the elderly, and there is no effective prevention and treatment at present.

Method used

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  • A kind of cemetine analogue, its synthesis method and its application
  • A kind of cemetine analogue, its synthesis method and its application
  • A kind of cemetine analogue, its synthesis method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 Synthesis

[0020] Weigh 200mg of the substrate 9-methyl-1,2,3,4,9,9a-6hydro-4aH-pyrido[2,3-b]indol-4a-ol and place in a 50mL dry round bottom In the flask, add 5mL of anhydrous pyridine and stir to dissolve, place the system in an ice-water bath at 0°C, and slowly add 0.07mL (0.72mmol) of acetic anhydride, the reaction reagent, to it dropwise. Detection, until the reaction is complete, add an appropriate amount of methanol dropwise to the reaction solution to quench the reaction, concentrate under reduced pressure to remove methanol and a small amount of pyridine, then extract 3 times with ethyl acetate, combine the organic phases, and successively wash with saturated CuSO 4 solution washed 3 times, saturated NaCl solution washed 3 times, anhydrous NaSO 4 dry. Concentrated under reduced pressure, the crude product was separated by column chromatography (PE:EA=6:1) to obtain 216 mg N-position acetylated derivative 1 (96%).

[0021] Character identificatio...

Embodiment 2

[0026] Synthesis

[0027] colorless oil, 1 H-NMR (400MHz, CDCl 3 ),δ7.34–7.04(m,2H),6.86–6.46(m,2H),5.30(s,1H),4.45–3.63(m,1H),3.29–3.17(m,1H),2.81(ddd ,J=13.1,8.3,4.8Hz,1H),2.64(d,J=25.6Hz,3H),2.58–2.34(m,2H),1.96–1.72(m,2H),1.67–1.24(m,2H ),1.17(dt,J=10.0,7.4Hz,3H). 13 C NMR (100MHz, CDCl 3 )δ 175.45(C), 149.54(C), 133.41(C), 129.52(CH), 129.33(CH), 122.04(CH), 119.06(CH), 108.34(CH), 85.36(C), 40.95(CH 2 ),37.20(CH 3 ), 33.29 (CH 2 ), 27.06(CH 2 ), 19.06, 9.60 (CH 3 ).

[0028] MS(ESI(+))calcd for C 15 h 20 N 2 o 2 [M+H] + :260.3; found: 261.0.

Embodiment 3

[0030]

[0031] Pale yellow oily, 1 H-NMR (400MHz, CDCl 3 ),δ7.26(s,2H),6.84–6.45(m,2H), 5.30(s,1H),4.44–3.62(m,1H),3.22(ddt,J=13.2,9.2,4.2Hz,1H ),3.01(s,1H), 2.80(ddd,J=13.1,8.3,4.8Hz,1H),2.63(d,J=32.5Hz,3H),2.55–2.23(m,2H), 1.96–1.74( m,2H),1.73–1.35(m,3H),0.96(dt,J=10.8,7.4Hz,3H). 13 C NMR (100MHz, CDCl 3)δ174.68(C), 149.54(C), 133.48(C), 129.27(CH×2), 122.03(CH), 119.02(CH), 108.30(CH), 85.35(C), 41.10(CH 2 ), 37.11 (CH 3 ), 35.31 (CH 2 ), 32.91 (CH 2 ), 19.40 (CH 2 ), 18.54 (CH 2 ),13.96.(CH 3 ).

[0032] MS(ESI(+))calcd for C 16 h 22 N 2 o 2 [M+H] + :274.4; found: 275.1.

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PUM

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Abstract

The present invention relates to a class of cypermeline analogs, a method for synthesizing the same and the use for inhibiting the activity of acetylcholinesterase. The preparation method of the described hemipramine analogue is based on 9-methyl-1,2,3,4,9,9a-6 hydrogen-4aH-pyrido[2,3-b]indole-4a- Alcohol is the substrate, add anhydrous pyridine to dissolve, slowly drop the reaction reagent organic acid or acid anhydride, after the reaction is complete, add a quenching agent to quench the reaction, and concentrate under reduced pressure to remove methanol and pyridine. The synthesis process is simple and the product purity is high. Inhibits acetylcholinesterase activity.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and in particular relates to a bacetin analogue, a synthesis method and an application thereof. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease whose etiology and pathogenesis have not been fully elucidated. It is characterized by memory loss and loss of daily behavior, cognitive impairment and personality changes. It is an important disease that affects the health of the elderly, and there is no effective prevention and treatment. [0003] Zhang Linlin et al. made a review from two aspects of the pathogenesis and therapeutic drugs of AD: the pathogenesis includes the Aβ-amyloid peptide cascade hypothesis related to the microenvironment, the theory of cholinergic damage, the theory of immune abnormality, etc., and the theory of Tau related to neurons. Protein hypothesis, nerve cell apoptosis theory, etc., gene-related apolipoprotein ε4 gene, presenilin 1 and pr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61P25/28
CPCA61P25/28C07D471/04
Inventor 郑绍军朱瑞魏洋韩珂唐冰蔡星伟
Owner JIANGSU UNIV OF SCI & TECH
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