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Dendrobium alkaloid derivatives as well as preparation method and medical application thereof

A technology of Dendrobium alkaloids and derivatives, which is applied in the direction of medical formulas, drug combinations, and medical preparations containing active ingredients, etc., and can solve problems such as reports and no biological activity of Pierardine

Active Publication Date: 2019-01-01
ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The origin of Dendrobium tiangong is southern China, and its main alkaloid active ingredient, pierardine, is a benzofuranone derivative. In the existing literature, the synthesis method of pierardine has been reported, but there is no report on the biological activity of pierardine
The structure of Pierardine is similar to that of butylphthalide (hereinafter referred to as NBP), and whether it has the similar biological activity of NBP has not been reported.

Method used

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  • Dendrobium alkaloid derivatives as well as preparation method and medical application thereof
  • Dendrobium alkaloid derivatives as well as preparation method and medical application thereof
  • Dendrobium alkaloid derivatives as well as preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Synthesis of 3-(2-(dimethylamino)ethyl)-1(3H)-isobenzofuranone (I-1)

[0071]

[0072] Step 1: 2-(3-Oxo-1,3-dihydroisobenzofuran-1-yl)acetic acid (2)

[0073] In a dry 100mL round bottom flask, sequentially add compound 1 (10.0g, 67mmol), oxalic acid (18.0g, 173mmol), sodium acetate (6.0g, 73mmol), add acetic acid (40mL) to dissolve, and raise the temperature under stirring to 100°C and keep warm for 10h. TLC [V (petroleum ether): V (ethyl acetate) = 1:5 as developing solvent] showed that the reaction was almost complete. Add water (60mL) and hydrochloric acid (2.0mol / L) to the reaction solution to adjust the pH value to about 3, and a white solid precipitates, which is filtered, washed with water (20mL×2), and dried in a blast drying oven (60°C) to obtain 6.6 g white solid compound 2, yield 51.6%; mp: 150-152°C.

[0074] Step 2: 3-(2-Hydroxyethyl)isobenzofuran-1(3H)-one (3)

[0075] In a dry 100mL round-bottomed flask, compound 2 (5.35g, 28mmol) and anhydrous te...

Embodiment 2

[0081] With reference to the synthetic method of Example 1, dimethylamine hydrochloride was replaced by tetrahydropyrrole, and a white solid 3-(2-(pyrrolidin-1-yl)isobenzofuran-1(3H)-one was obtained by hydrochloric acid salification Hydrochloride (I-2), yield 73.1%. 1 HNMR (400MHz, D 2 O): δ7.78(dd, J=7.9, J=1.1, 1H), 7.70(td, J=7.7, J=1.1, 1H), 7.50~7.55(m, 2H), 5.67(dd, J= 8.5, J= 3.2, 1H), 3.47~3.64(s, 2H), 3.12~3.32(m, 2H), 2.86~3.02(m, 2H), 2.94(s, 2H), 2.47~2.59(m, 1H ),2.05~2.17(m,1H),1.99(s,2H),1.88(s,2H); 13 CNMR (100MHz,D 2 O)δ: 173.06, 148.54, 135.33, 129.79, 125.40, 124.43, 122.13, 79.87, 54.37, 54.08, 50.91, 29.85, 22.54; ESI-MS: m / z=232.2[M+H] + .

Embodiment 3

[0083] With reference to the synthetic method of Example 1, dimethylamine hydrochloride was replaced by tetrahydrothienopyridine, and a white solid 3-(2-(6,7-dihydrothieno[3,2-c]pyridine was obtained through hydrochloric acid salification) -5(4H)-yl)ethyl)isobenzofuran-1(3H)-one hydrochloride (I-3), yield 63.5%. 1 H-NMR (400MHz, DMSO-d 6 ): δ11.36(s,1H),7.81~7.93(m,2H),7.76(d,J=7.8,1H),7.66(t,J=6.9,1H),7.49(d,J=5.3, 1H),6.86~6.95(m,1H),5.75~5.86(m,1H),4.47~4.59(m,1H),4.12~4.29(m,1H),3.74~3.87(m,1H),3.17~ 3.54(m,2H),3.39(s,2H),3.01~3.17(m,1H),2.72~2.86(m,1H),2.16~2.34(m,1H); 13 C-NMR (100MHz, DMSO-d 6 ))δ: 169.94, 149.51, 135.12, 131.83, 130.13, 128.60, 125.67, 125.62, 125.58, 125.47, 123.22, 79.03, 51.86, 51.80, 50.70, 50.62, 49.53, 499.42,2 z=300.1[M+H] + .

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Abstract

The invention relates to the field of medicinal chemistry, in particular to dendrobium alkaloid derivatives (I); pharmacodynamic experiments prove that the compounds provided by the invention has protection activity for neuron injury caused by N-methyl-D-aspartate receptor (NMDA), thus being used for preventing and treating neuron injury diseases. (The structural formula of the dendrobium alkaloidderivatives (I) is described in the description.).

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of dendrobium alkaloid derivatives and their preparation methods and medical applications. The compounds of the invention have protective activity against neuron damage caused by NMDA and can be used to prevent and treat nerve damage diseases. Background technique [0002] Nerve injury disease is a neurological disease caused by damage or death of neuron cells, such as neurological impairment caused by stroke, Parkinson's disease, Alzheimer's disease, etc. Seriously affect the life, health and normal life of patients. The main characteristics of neuronal cell damage include metabolic imbalance caused by ischemia and hypoxia, oxidative stress, excitatory amino acid toxicity, calcium overload, inflammatory response, etc., resulting in massive death of neurons. [0003] N-methyl-D-aspartic acid receptor (NMDA) receptors are postsynaptic ionotropic receptors that respond i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88C07D407/06C07D495/04A61K31/365A61K31/5377A61K31/4025A61K31/4525A61K31/4365A61K31/496A61P25/28A61P25/08A61P25/16A61P9/10A61P21/00
CPCA61P9/10A61P21/00A61P25/08A61P25/16A61P25/28C07D307/88C07D407/06C07D495/04
Inventor 李家明何广卫胡孟奇储昭兴许勤龙王玉峻杨雨刘万东高憟繁莫佳佳
Owner ANHUI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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