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Indole compound and application and preparation method thereof

A compound, indole technology, applied in the field of medicine, can solve the problems of lack of effective tumor treatment, anti-tumor drugs can not meet the treatment and other problems, and achieve significant effects, anti-cancer effects, and good inhibitory effects.

Active Publication Date: 2020-05-08
GUANGZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the anti-tumor drugs currently used in clinical practice are far from meeting the requirements of treatment, and there is still a lack of effective drugs for the treatment of tumors.

Method used

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  • Indole compound and application and preparation method thereof
  • Indole compound and application and preparation method thereof
  • Indole compound and application and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0096] The synthesis of embodiment 1 compound 3a

[0097]

[0098]Take a 100mL reaction bottle, evacuate it, fill it with nitrogen, and repeat the operation three times, then add 2a (421mg, 3.6mmol) to the bottle, then add DMF (30mL), stir at 0°C, and slowly add NaH in batches (60% distribution in mineral oil, 180 mg, 4.5 mmol) into the stirred solution. After stirring at 0°C for 30 minutes, 1a (590mg, 3.0mmol) was added, and the reaction was stirred at room temperature for 20 hours, then 100mL of water was added to quench the reaction, extracted with ethyl acetate (50mL×3), and the organic phase was washed with Dry over anhydrous sodium sulfate. After filtration, the filtrate was spin-dried (the solvent was evaporated under reduced pressure), and separated by silica gel column chromatography (petroleum ether / ethyl acetate=5 / 1) to obtain the yellow solid product 3a (749 mg, 90%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ=9.18(...

Embodiment 2

[0099] The synthesis of embodiment 2 compound 3b

[0100]

[0101] According to the method described in Example 1, 2a (421mg, 3.6mmol) was added to a 100mL reaction flask under nitrogen atmosphere, then DMF (30mL) was added, stirred at 0°C, and NaH was slowly added in batches (in Distribute 60% in mineral oil, 180 mg, 4.5 mmol) into the stirred solution. After stirring at 0°C for 30 minutes, 1b (497mg, 3.0mmol) was added, and the reaction was stirred at room temperature for 20 hours, then 100mL of water was added to quench the reaction, extracted with ethyl acetate (50mL×4), and the organic phase was washed with Dry over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column chromatography to obtain product 3b (523 mg, 70%) as a yellow solid. The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ=9.11(d, J=2.9Hz, 1H), 9.03(d, J=8.3Hz, 1H), 8.79(s, 1H), 7.86(s, 1H), 7.62(d, J=7.6Hz, 1H), 7.36 (t, J = 7.7H...

Embodiment 3

[0102] The synthesis of embodiment 3 compound 3c

[0103]

[0104] According to the method described in Example 1, 2a (421mg, 3.6mmol) was added to a 100mL reaction flask under nitrogen atmosphere, then DMF (30mL) was added, stirred at 0°C, and NaH was slowly added in batches (in Distribute 60% in mineral oil, 180 mg, 4.5 mmol) into the stirred solution. After stirring at 0°C for 30 minutes, 1c (732 mg, 3 mmol) was added, and the reaction was stirred at room temperature for 20 hours to obtain the product 3c (580 mg, 60%) as a white solid. The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ=9.17(d, J=3.7Hz, 1H), 9.09(d, J=8.5Hz, 1H), 8.86(s, 1H), 7.94(s, 1H), 7.65(d, J=7.7Hz, 1H), 7.40–7.29 (m, 7H), 6.80 (d, J=3.6Hz, 1H). 13 CNMR (100MHz, CDCl 3 ) δ = 152.8, 152.3, 150.0, 142.3, 136.2, 135.3, 130.8, 129.2, 128.7, 128.6, 127.9, 124.0, 123.0, 122.3, 120.9, 117.4, 108.6, 47.4. HR-MS(ESI)m / z calcd for C 20 h 16 N 5 [M+H] + 326.1400,fou...

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Abstract

The invention relates to an indole compound and application and a preparation method thereof. The structural formula of the indole compound is as shown in a formula (I) which is described in the specification. The novel indole compound disclosed by the invention has an inhibiting effect on lumen formation of human umbilical vein endothelial cells (HUVEC), is applicable to treatment of pathologicalangiogenesis related diseases, is particularly suitable for preventing and treating tumors and rheumatoid arthritis, and has a relatively high application value.

Description

technical field [0001] The invention relates to the field of medicine, in particular to an indole compound and its application and preparation method. Background technique [0002] Malignant tumors are one of the diseases that pose a great threat to human health. According to relevant statistics from the China Cancer Management Center, the incidence and death of malignant tumors in China have shown an upward trend in recent years. According to the 2018 global cancer statistics report of the official journal of the American Cancer Society "Journal of Cancer for Clinicians", the cancers with the largest number of new cases and deaths are lung cancer, breast cancer, prostate cancer, colon cancer, non-melanoma of the skin, gastric cancer, Liver cancer, rectal cancer, etc. Clinically, drug therapy is still the main treatment for tumors. However, the anti-tumor drugs currently used in clinical practice are far from meeting the requirements of treatment, and there is still a lack...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D473/34C07D519/00C07F5/02A61P35/00A61P35/02A61P19/02A61P29/00A61K31/52A61K31/69
CPCA61P19/02A61P29/00A61P35/00A61P35/02C07D473/34C07D519/00C07F5/025
Inventor 阮志雄余细勇王玉青雷雪萍徐中楠
Owner GUANGZHOU MEDICAL UNIV
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