Isopropanolamine substituted beta-elemene derivative and preparation method and application thereof

A technology of isopropanolamine and elemene, which is applied in the field of preparation of antitumor drugs, can solve the problems of low bioavailability and limited wide application

Active Publication Date: 2017-07-07
YUAN INT GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, β-elemene is a volatile oil, insoluble in water, and its bioavailability is very low, which limits its wide application in clinical practice.

Method used

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  • Isopropanolamine substituted beta-elemene derivative and preparation method and application thereof
  • Isopropanolamine substituted beta-elemene derivative and preparation method and application thereof
  • Isopropanolamine substituted beta-elemene derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Synthesis of N,N-diethylisopropanolamine-β-elemene

[0102] Dissolve 0.5mmol glycidyl ether β-elemene and 1.5mmol diethylamine in 1mL methanol, add 0.05mmol Zn(ClO 4 ) 2 ·6H 2 O, stirred at 80 °C for 1 h. Cool to room temperature, add water, extract with dichloromethane, dry over anhydrous sodium sulfate, filter, evaporate dichloromethane under reduced pressure, and use dichloromethane:methanol=40:1 column chromatography to obtain a light yellow liquid product with a yield of 66%. 1 H NMR (300MHz, CDCl 3 )δ5.75(dd, J=17.8, 10.5Hz, 1H), 4.94(s, 1H), 4.91(s, 1H), 4.85(d, J=3.8Hz, 1H), 4.81(s, 1H), 4.75(s, 1H), 4.51(s, 1H), 4.25–4.12(m, 2H), 4.02–3.86(m, 2H), 3.58–3.41(m, 2H), 3.38–3.21(m, 4H), 3.20–3.14(m, 2H), 2.02–1.84(m, 2H), 1.64(s, 3H), 1.63–1.49(m, 3H), 1.48–1.28(m, 9H), 0.93(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ 149.55, 149.30, 147.06, 111.67, 110.06, 109.52, 73.29, 70.93, 64.45, 55.21, 52.13, 48.32, 40.92, 39.34, 39.27, 32.68, 26.59, 24.35, 16.06, 8.3

Embodiment 2

[0104] Synthesis of tetrahydropyrrole-β-elemene with isopropanol

[0105] Tetrahydropyrrole was used instead of diethylamine, and other conditions were the same as in Example 1 to obtain a light yellow liquid product with a yield of 73%. 1H NMR (300MHz, CDCl3) δ5.82(dd, J=17.8, 10.5Hz, 1H), 5.02(s, 1H), 4.98(s, 1H), 4.92(d, J=3.9Hz, 1H), 4.88 (s, 1H), 4.82(s, 1H), 4.58(s, 1H), 4.38(s, 1H), 4.25–4.12(m, 1H), 4.07–3.93(m, 2H), 3.75–3.12(m , 8H), 2.27–2.09(m, 4H), 2.06–1.87(m, 2H), 1.71(s, 3H), 1.68–1.50(m, 3H), 1.52–1.30(m, 3H), 1.00(s , 3H); 13C NMR (75MHz, CDCl3) δ149.56, 149.34, 147.09, 111.67, 109.97, 109.53, 73.22, 70.94, 65.52, 58.18, 54.98, 52.11, 40.88, 39.34, 39.28, 32.66, 24.35 , 16.06.

Embodiment 3

[0107] Synthesis of isopropanol piperidine-β-elemene

[0108] Piperidine was used instead of diethylamine, and other conditions were the same as in Example 1 to obtain a light yellow liquid product with a yield of 68%. 1 H NMR (300MHz, CDCl 3 )δ5.82(dd, J=17.8, 10.5Hz, 1H), 5.02(s, 1H), 4.98(s, 1H), 4.92(d, J=4.0Hz, 1H), 4.88(s, 1H), 4.82(s, 1H), 4.58(s, 1H), 4.38(s, 1H), 4.30–4.20(m, 1H), 4.08–3.94(m, 2H), 3.57–3.44(m, 2H), 3.33– 3.08(m, 6H), 2.08–1.81(m, 6H), 1.71(s, 3H), 1.69–1.54(m, 5H), 1.53–1.41(m, 3H), 1.00(s, 3H); 13 C NMR (75MHz, CDCl 3 )δ149.58, 149.41, 147.08, 111.66, 110.01, 109.50, 73.24, 71.25, 64.48, 60.21, 54.25, 52.14, 40.86, 39.35, 39.29, 32.65, 26.56, 24.35, 22.909, 21.0

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Abstract

The invention relates to an isopropanolamine substituted beta-elemene derivative and a preparation method and an application of the isopropanolamine substituted beta-elemene derivative. Particularly, the invention relates the novel isopropanolamine substituted beta-elemene derivative shown in the general formula (I) or (II), the preparation method of the isopropanolamine substituted beta-elemene derivative, and the application of the isopropanolamine substituted beta-elemene derivative to preparation of antitumor drugs.

Description

technical field [0001] The present invention relates to new isopropanolamine substituted β-elemene derivatives, their preparation method and their use. In particular, the present invention relates to novel isopropanolamine-substituted β-elemene derivatives and their use in the preparation of antitumor drugs. Background technique [0002] Tumor refers to the neogrowth formed by the proliferation of local tissue cells in the body under the action of various tumorigenic factors, because this neogrowth is mostly in the form of space-occupying blocky protrusions, also known as neoplasm (neoplasm) . According to the cell characteristics of new organisms and the degree of harm to the body, tumors are divided into two categories: benign tumors and malignant tumors, and cancer is the general term for malignant tumors. [0003] Malignant tumor is one of the main diseases that endanger human health. In some countries where infectious diseases have been basically controlled, cardiova...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/28C07C217/30C07C217/34C07C213/04C07D295/088C07D211/22C07D307/52A61K31/133A61K31/136A61K31/137A61K31/138A61K31/40A61K31/445A61K31/4453A61K31/5375A61K31/495A61K31/496A61P35/00
CPCC07C213/04C07C217/28C07C217/30C07C217/34C07D211/22C07D295/088C07D301/28C07D303/22C07D307/52
Inventor 徐进宜陈继超王天雨许海王若研许婷陈晓彤
Owner YUAN INT GROUP
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