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2-substituted-beta-carboline compounds and application thereof in preparing drugs for preventing or treating tumors

A compound, carboline technology, applied in the field of preparation of 2-substituted β-carboline compounds, can solve the problems of tumor treatment failure and achieve good inhibitory effect

Inactive Publication Date: 2015-04-29
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of effective anti-tumor drugs have been developed, the failure of treatment will be caused by tumor metastasis and drug resistance. Therefore, the continuous development of new anti-tumor drugs is of great significance

Method used

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  • 2-substituted-beta-carboline compounds and application thereof in preparing drugs for preventing or treating tumors
  • 2-substituted-beta-carboline compounds and application thereof in preparing drugs for preventing or treating tumors
  • 2-substituted-beta-carboline compounds and application thereof in preparing drugs for preventing or treating tumors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] This embodiment is the synthesis of 1-methyl-2-benzyl-7-methoxy-9-octyl-β-carboline chloride salt (compound 1):

[0042]

[0043] Add 1mmol of 1-methyl-7-methoxy-9-octyl-β-carboline into a 50mL round bottom flask, add 25mL of ethyl acetate and 2mmol of benzyl chloride, and react at 80°C for 24h; , separated by silica gel column chromatography to obtain 1-methyl-2-benzyl-7-methoxy-9-octyl-β-carboline chloride salt (1) (0.34 mmol, yield 34%). 1H-NMR (400MHz, MeOD): 8.65(d, J=6.6Hz, 1H), 8.48(d, J=6.6Hz, 1H), 8.30(d, J=8.7Hz, 1H), 7.40-7.49(m ,3H),7.21-7.24(br,3H),7.12(dd,J=2.1,8.8Hz,1H),6.04(s,2H),4.69(t,J=7.6Hz,2H),4.69(s, 3H), 3.32-3.34(m, 2H), 1.83-1.90(m, 2H), 1.26-1.42(m, 10H), 0.88(t, J=6.87Hz, 3H); 13C-NMR(400MHz, MeOD) :δ164.64,148.23,135.35,134.31,134.17,129.24(2C),128.50,126.44(2C),124.03,113.86,113.42,113.05,93.14,60.37,55.26,45.44,31.53,30.06,28.94,28.83,26.24,22.21 ,13.05; ESI-MS m / z:451.2[M+H] + .

Embodiment 2

[0045] This embodiment is the synthesis of 1-methyl-2-benzyl-7-methoxy-9-allyl-β-carboline chloride salt (compound 2):

[0046] With reference to the synthetic route shown in Example 1, 1mmol of 1-methyl-7-methoxy-9-allyl-β-carboline was added to a 50mL round bottom flask, and 25mL of ethyl acetate and 2mmol of chlorine were added Benzyl chloride, reacted at 80°C for 24h; after reducing the concentration, silica gel column chromatography separated to obtain 1-methyl-2-benzyl-7-methoxy-9-allyl-β-carboline chloride salt ( 2) (0.35 mmol, 35% yield). 1 H-NMR (400MHz, MeOD): 8.65(d, J=6.6Hz, 1H), 8.49(d, J=6.6Hz, 1H), 8.32(d, J=8.7Hz, 1H), 7.45-7.40(m ,3H),7.21(d,J=6.94Hz,1H),7.15(d,J=5.15Hz,1H),7.13(d,J=8.7Hz,1H),6.02(s,2H),5.33(m ,2H),5.28(d,J=10.62Hz,1H),5.56(s,3H),4.01(s,3H); 13 C-NMR (MHz, MeOD): 164.82, 148.35, 139.14, 135.86, 135.55, 134.20, 134.11, 133.25, 129.17 (2C), 128.65, 126.43 (2C), 124.10, 115.58, 114.03, 113.407, 1903 ,55.21; ESI-MS m / z:379.3[M+H] +.

Embodiment 3

[0048] This example is the synthesis of 1-methyl-2-benzyl-7-methoxy-9-(4-methyl)benzyl-β-carboline chloride salt (compound 3):

[0049] Referring to the synthetic route shown in Example 1, 1mmol of 1-methyl-7-methoxy-9-(4-methyl)benzyl-β-carboline was added to a 50mL round bottom flask, and 25mL of acetic acid was added Ethyl ester and 2mmol benzyl chloride were reacted at 80°C for 24h; after reducing the concentration, silica gel column chromatography separated to obtain 1-methyl-2-benzyl-7-methoxy-9-(4-methyl) Benzyl-β-carboline chloride salt (3) (0.41 mmol, 41% yield). 1 H-NMR (400MHz, MeOD): 8.66(d, J=6.6Hz, 1H), 8.53(d, J=6.6Hz, 1H), 8.37(d, J=8.8Hz, 1H), 7.37-7.41(m ,3H),7.19(d,J=9.78Hz,1H),7.12-7.17(m,5H),6.90(d,J=8.0Hz,2H),5.96(s,2H),5.94(s,2H) ,3.95(s,3H),2.93(s,3H),2.30(s,3H); 13 C-NMR(400MHz,MeOD):164.89,148.92,139.48,137.61,135.90,135.74,134.55,134.22,133.76,129.58,129.08,128.55,126.30,125.04,124.23,114.09,113.84,113.11,92.86,60.33,55.25 ,48.50,19.64,15.27; ESI...

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Abstract

The invention provides 2-substituted-beta-carboline compounds and application thereof in preparing drugs for preventing or treating tumors. The structural general formula of the compounds is disclosed as Formula I. The compounds have high inhibiting actions on growth of tumor cells, and have approximate activity to the positive control paclitaxel. Part of the compounds have obviously better antitumor activity than the paclitaxel; the IC50 value is less than 1 mu M; and thus, the compounds can become efficient drugs for treating tumors.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, in particular to a preparation method of 2-substituted β-carboline compounds and their antitumor application. Background technique [0002] At present, tumors (especially malignant tumors) are one of the major diseases that threaten human health and life. Although a variety of effective anti-tumor drugs have been developed, the failure of treatment will be caused by tumor metastasis, drug resistance and other reasons. Therefore, the continuous development of new anti-tumor drugs is of great significance. Searching for anti-tumor active ingredients from natural products, using the obtained active ingredients as precursor compounds, and modifying them is one of the main approaches for the development of anti-tumor drugs. Contents of the invention [0003] Aiming at the defects or deficiencies of the prior art, the present invention provides a 2-substituted β-carboline compound, the g...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/437A61P35/00
CPCC07D471/04
Inventor 王俊儒杜宏涛李娜谷红玲刘丙蕊
Owner NORTHWEST A & F UNIV
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