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Beta-carboline alkali derivative compounds and application thereof

A carboline base and derivative technology is applied in the field of β-carboline base derivatives of the general formula, and can solve the problems of limited application prospects, poor water solubility of β-carboline base derivatives, and insufficient antitumor activity.

Active Publication Date: 2013-01-30
新疆华世丹药业股份有限公司
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  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

However, studies have found that most of the β-carboline base derivatives are either poor in water solubility or have insufficient antitumor activity, which limits their application prospects

Method used

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  • Beta-carboline alkali derivative compounds and application thereof
  • Beta-carboline alkali derivative compounds and application thereof
  • Beta-carboline alkali derivative compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] Preparation of Example 11-(4-methoxy)phenyl-3-[N-(2-diethylamino)-ethyl]-methylamino-β-carboline (compound 1)

[0122] Starting material Ethyl 1-(4-methoxy)phenyl-β-carboline-3-carboxylate was synthesized according to literature method.

[0123] Step (a): Preparation of 1-(4-methoxy)phenyl-3-hydroxymethyl-β-carboline:

[0124] Ethyl 1-(4-methoxy)phenyl-β-carboline-3-carboxylate (10mmol), THF (200ml), LiBH 4 (30mmol) after mixing, stir and react at room temperature for 12h, TLC (petroleum ether / acetone=1 / 1) follow-up detection, the reaction is completed, the reaction mixture is slowly poured into 200ml ice water, stirred for 10 minutes, concentrated hydrochloric acid is added dropwise to pH 2-3, stirred at room temperature for 2 hours, cooled the mixture with ice water, adjusted the pH value to 9-10 with sodium hydroxide solution, extracted with ethyl acetate, washed with water, washed with saturated saline, dried with anhydrous sodium sulfate, decolorized with activate...

Embodiment 2

[0131] Preparation of Example 21-(4-methoxy)phenyl-3-[N-(3-dimethylamino)-propyl]-methylamino-β-carboline (compound 2)

[0132] The preparation method is the same as in Example 1, but step (c) uses N,N-dimethylpropylenediamine as raw material. Obtain yellow oil, be target compound 2, yield 42%; IR (KBr, cm -1 )v: 2947, 2744, 1621, 1510, 1464, 1378, 1259, 1181, 1024, 756; 1 H NMR (500MHz, D 2 O): δ8.20(s, 1H), 7.93(d, J=8Hz, 1H), 7.63(d, J=9Hz, 2H), 7.44-7.48(m, 1H), 7.35(d, J=8.5 Hz, 1H), 7.15-7.18(m, 1H), 7.03(d, J=8.5Hz, 2H), 4.64(s, 2H), 3.77(s, 3H), 3.32-3.35(m, 2H), 3.26 -3.30(m, 2H), 2.90(s, 6H), 2.22-2.28(m, 2H); 13 C NMR (100MHz, D 2 O+Dioxane): δ161.9, 143.4, 139.0, 132.7, 131.8, 131.5, 131.0, 130.8, 122.5, 122.0, 120.9, 119.3, 117.1, 115.1, 112.4, 55.6, 54.2, 47.7, 44.8, 42.9, 21.3 -MS m / z: 389.3(M+1) + .

[0133] The preparation method of compound 2 hydrochloride is the same as that in Example 1.

Embodiment 3

[0134] Example 3 Preparation of 1-(4-methoxy)phenyl-3-[N-(3-diethylamino)-propyl]-methylamino-β-carboline (compound 3)

[0135] The preparation method is the same as in Example 1, but step (c) uses N,N-diethylpropylenediamine as raw material. Obtain yellow oil, be target compound 3, yield 50%; IR (KBr, cm -1 )v: 2941, 2740, 1628, 1510, 1449, 1380, 1257, 1181, 1025, 756; 1 H NMR (500MHz, D 2 O): δ8.34(s, 1H), 8.11(d, J=8.5Hz, 1H), 7.78(d, J=9Hz, 2H), 7.62(t, J=7Hz, 1H), 7.51(d, J=8Hz, 1H), 7.33(t, J=7.5Hz, 1H), 7.19(d, J=8.5Hz, 2H), 4.75(s, 2H), 3.92(s, 3H), 3.43(t, J =7.5Hz, 2H), 3.29-3.36(m, 6H), 2.28-2.34(m, 2H), 1.35(t, J=7.5Hz, 6H);13 C NMR (125MHz, D 2 O): δ162.3, 143.8, 139.6, 133.2, 132.2, 132.1, 131.6, 131.2, 122.9, 122.4, 121.6, 119.8, 117.4, 115.5, 112.9, 56.1, 48.8, 48.2, 48.0, 45.3, 21.2, 8. -MS m / z: 417.4(M+1) + .

[0136] The preparation method of compound 3 hydrochloride is the same as that in Example 1.

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Abstract

The invention relates to beta-carboline alkali derivative compounds and application thereof. Novel beta-carboline alkali derivative compounds are synthesized by structurally modifying the first, third and ninth sites of beta-carboline parent nucleus and importantly introducing amido into the first and third sites; and the obvious anti-tumor activity of the compounds is kept, and the water solubility of the compounds is improved. A method for preparing the compounds is simple and convenient, the yield is high, and the beta-carboline alkali derivative compounds can be used for preparing medicines for treating various tumor diseases.

Description

technical field [0001] The present invention relates to pharmaceutical compounds, especially alkaloid compounds, more specifically to compounds of general formula (I) β-carboline base derivatives and applications thereof. Background technique [0002] β-carboline compounds are a large class of natural or chemically synthesized alkaloids, which have broad-spectrum pharmacological activities, such as antitumor, antibacterial, antiparasitic, antiviral and so on. Before 2000, domestic and foreign research reports mainly focused on the neuropharmacological activity of these compounds. Since 2000, the antitumor activity of β-carboline base compounds has aroused people's interest, and domestic and foreign literatures describe the synthesis and antitumor activity of a large number of β-carboline base compounds. For example, Ishida et al. [Bioorg.Med.Chem.Lett.9 (1999) 3319-3324.] carried out structural modification on the 7 and 9 positions of dehydrohalamine and studied the structu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A61K31/437A61P35/00
Inventor 王子厚曹日晖陈志勇武嘉林郭亮马芹范文玺孙洁
Owner 新疆华世丹药业股份有限公司
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