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Novel indoles compound having anti-tumor metastasis activity and anti-inflammatory activity, as well as synthesis and application of novel indoles compound

A reactive, hydroxyethyl technology, applied in the fields of inhibiting tumor weight gain, anti-tumor lung metastases and anti-inflammatory activities in S180 tumor-bearing mice, which can solve problems such as low quality of life and side effects

Active Publication Date: 2017-01-25
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Surgery, radiotherapy, chemotherapy can cause serious side effects, resulting in poor quality of life for patients

Method used

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  • Novel indoles compound having anti-tumor metastasis activity and anti-inflammatory activity, as well as synthesis and application of novel indoles compound
  • Novel indoles compound having anti-tumor metastasis activity and anti-inflammatory activity, as well as synthesis and application of novel indoles compound
  • Novel indoles compound having anti-tumor metastasis activity and anti-inflammatory activity, as well as synthesis and application of novel indoles compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1 liquid phase connection peptide reaction general method

[0021] Dissolve the carboxyl-terminally exposed compound in anhydrous tetrahydrofuran (THF), add N-hydroxybenzotriazole (HOBt) to the obtained solution, and slowly add N,N-dicyclohexylcarbon dissolved in anhydrous THF under ice-cooling Diimine (DCC), stirred at 0°C for 15 minutes to obtain the reaction solution (I). The carboxy-terminally protected amino acid was also dissolved in anhydrous THF, adjusted to pH 9 with N-methylmorpholine (NMM), then mixed with the reaction solution (I), maintained at pH 9 with N-methylmorpholine, and stirred at room temperature for 10 h. The progress of the reaction was monitored by TLC. After the raw material point disappeared, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to obtain a viscous substance, which was dissolved in ethyl acetate or dichloromethane, and the obtained solution was sequentially washed with 5% NaHCO...

Embodiment 2

[0022] Example 2 Preparation of 5-(bis(3-(2-hydroxyethyl)-1H-indole-2)methyl)-2-hydroxybenzoic acid methyl ester (3)

[0023] 1.66g (10mmol) of methyl 5-formylsalicylate, 3.22g (20mmol) of indole alcohol and 0.17g (1mmol) of p-toluenesulfonic acid were dissolved in 50mLTHF, reacted at 60°C for 10h, and monitored by TLC (CH 2 Cl 2 :CH 3 OH=30:1) the raw material point disappeared, the reaction was stopped, cooled to room temperature, concentrated to dryness under reduced pressure, the residue was dissolved in dichloromethane, and 3.8 g (78%) of light yellow powder was obtained by silica gel column chromatography. IR: 3375, 3055, 1672, 1487, 1456, 1208, 1088, 738cm -1 ;FT-MS(m / e):485.20627[M+H] + (calculated: 484.19982); 1 H NMR (800MHz, DMSO-d6) δ=10.52(s, 2H), 10.47(s, 1H), 7.58(s, 1H), 7.50(d, J=8.0Hz, 2H), 7.30(d, J= 8.0Hz, 2H), 7.25(d, J=8.8Hz, 2H), 7.04(t, J=7.2Hz, 2H), 6.97(t, J=7.2Hz, 2H), 6.95(d, J=8.8Hz , 1H), 6.08 (s, 1H), 3.80 (s, 3H), 3.53 (m, 2H), 3.49 (m, 2H...

Embodiment 3

[0024]Example 3 Preparation of 5-(bis(3-(2-hydroxyethyl)-1H-indole-2)methyl)-2-hydroxybenzoic acid (4)

[0025] Under ice bath, 1.2g (2.4mmol) 5-(bis(3-(2-hydroxyethyl)-1H-indole-2)methyl)-2-hydroxybenzoic acid methyl ester (3) was dissolved in methanol, added 4N NaOH aqueous solution, adjust the pH value to 12, react for 48h, TLC plate monitoring (CH 2 Cl 2 :CH 3 OH=20:1) The raw material point disappears and the reaction is complete. saturated KHSO 4 Adjust the reaction solution to neutral, concentrate under reduced pressure to remove methanol, continue to adjust the pH value of the residue to 3, extract 3 times with ethyl acetate, combine the ethyl acetate phases, dry with anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 1.08 g (93%) of the title compound as a light gray solid. IR: 3367, 1667, 1457, 1215, 1038, 740cm -1 ;FT-MS (m / e): 469.17775[M-H] - (calculated: 470.18417); 1 HNMR (800MHz, DMSO-d6) δ=10.53(s, 2H), 7.53(s, 1H), 7.50...

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Abstract

The invention discloses 20 kinds of 5-(bi(3-(2-ethoxy)-1H-indol-2)methyl)-2-hydroxy benzoyl-AA-OBzl, discloses a preparation method of the 5-(bi(3-(2-ethoxy)-1H-indol-2)methyl)-2-hydroxy benzoyl-AA-OBzl, discloses an effect of the 5-(bi(3-(2-ethoxy)-1H-indol-2)methyl)-2-hydroxy benzoyl-AA-OBzl in inhibiting invasion and metastasis of a tumor cell, discloses an activity of the 5-(bi(3-(2-ethoxy)-1H-indol-2)methyl)-2-hydroxy benzoyl-AA-OBzl in inhibiting weight gain of a tumor body of a S180-bearing mouse, and discloses an anti-tumor pulmonary metastasis activity and an anti-inflammatory activity. The compound has an excellent application prospect in preparing an antitumor drug, an anti-tumor metastasis drug and an anti-inflammatory drug.

Description

technical field [0001] The present invention relates to 20 kinds of 5-(bis(3-(2-hydroxyethyl)-1H-indole-2)methyl)-2-hydroxybenzoyl-AA-OBzl, to their preparation methods, to their Inhibition of tumor cell invasion and metastasis involves their activity in inhibiting tumor weight gain in mice bearing S180 tumors, and their anti-tumor lung metastasis activity and anti-inflammatory activity. The compound of the invention has good application prospects in the preparation of anti-tumor drugs, anti-tumor metastasis drugs and anti-inflammatory drugs. The invention belongs to the field of biomedicine. Background technique [0002] Malignant tumors seriously threaten human life and health. Lung cancer is one of the most aggressive human cancers. For patients with advanced lung cancer, usually 10%-15% of them can only survive for 5 years. This difficult situation has not improved significantly over the past 30 years. In many clinical cases, lung cancer has metastasized to surround...

Claims

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Application Information

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IPC IPC(8): C07D209/18C07D403/14C07D209/20A61P35/00A61P35/04A61P29/00
CPCC07D209/18C07D209/20C07D403/14
Inventor 赵明彭师奇吴建辉王玉记甘太平
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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