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3-hydroxyindole-2-ketone compounds for antitumor medicaments

A technology of ketone compounds and anti-tumor drugs, which is applied in the field of 3-hydroxyindole-2-one compounds for anti-tumor drugs, can solve problems such as the inability to design small molecule inhibitors, and achieve the prevention of tumor growth and metastasis. , the effect of inhibiting proliferation, strong inhibitory effect

Active Publication Date: 2014-03-05
ZUNYI MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since EWS-FLI1 is a misplaced protein, conventional structure-based methods cannot be used to design small-molecule inhibitors

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] Preparation of 1-methyl-3-hydroxy-3-[6-bromo-2,3-dihydroquinolin-4-one-3-yl]indol-2-one (I-1)

[0063] Dissolve 1-methyl-isatin (1.61 g, 10 mmol) and 6-bromo-2,3-dihydroquinolin-4-one (2.26 g, 10 mmol) in absolute ethanol (10 mL), and add three Ethylamine (0.5mL), the system was heated to 40°C, stirred and reacted for 2h, the precipitated solid was filtered with suction, washed with absolute ethanol (2 × 1mL), and dried in vacuo to obtain 2.78g of a yellow solid with a yield of 72%, m.p. 189~191°C. 1 H NMR (DMSO-d6, 300MHz) δ (ppm): 7.23~7.29(m, 4H), 7.17(d, J = 3.3 Hz, 1H), 6.94~6.99(m, 2H), 6.75(d, J= 8.4 Hz, 1H), 6.15(s, 1H), 3.70~3.91(m, 2H), 3.50-3.57(m, 1H), 3.10(s, 3H); ESI-MS m / z: 386.9 [M+H ] + ; Anal. calcd for C 18 h 15 BrN 2 o 3 (387.23): C55.83, H3.90, N7.23; found: C55.48, H4.10, N7.0.

Embodiment 2

[0065] Preparation of 1-methyl-3-hydroxy-3-[6-chloro-2,3-dihydroquinolin-4-one-3-yl]indol-2-one (I-2)

[0066] Dissolve 1-methyl-isatin (1.61 g, 10 mmol) and 6-chloro-2,3-dihydroquinolin-4-one (1.81 g, 10 mmol) in absolute ethanol (10 mL), and add three Ethylamine (0.5mL), the system was heated to 40°C, stirred for 2h, the precipitated solid was filtered with suction, washed with absolute ethanol (2 × 1mL), and dried in vacuo to obtain 2.56g of a yellow solid with a yield of 75%, m.p. 191~193°C. 1 H NMR (DMSO-d6, 300 MHz) δ (ppm): 7.23~7.28(m, 4H), 7.15(d, J = 3.3 Hz, 1H), 6.94~6.99(m, 2H), 6.75(d, J = 8.6 Hz, 1H), 6.14(s, H), 3.81~3.89(m, 1H), 3.75(t, J = 14.0 Hz, 1H), 3.50(dd, J = 6.1 and 14.1 Hz, 1H), 3.10 (s,3H); ESI-MS m / z: 365.1 [M+Na] + ; Anal. calcd for C 18 h 15 ClN 2 o 3 (342.78): C63.07, H4.41, N8.17; found: C63.04, H4.56, N7.9.

Embodiment 3

[0068] Preparation of 1-ethyl-3-hydroxy-3-[6-bromo-2,3-dihydroquinolin-4-one-3-yl]indol-2-one (I-3)

[0069] 1-Ethyl-isatin (1.75 g, 10 mmol) and 6-bromo-2,3-dihydroquinolin-4-one (2.26 g, 10 mmol) were dissolved in

[0070] Add triethylamine (0.5 mL) to absolute ethanol (10 mL), heat the system to 40 °C, stir for 2 h, filter the precipitated solid with suction, wash with absolute ethanol (2 × 1 mL), and dry in vacuo to obtain Yellow solid 2.84g, yield 71%, m.p. 202~205℃. 1 H NMR (DMSO-d 6 , 300 MHz) δ (ppm): 7.24~7.39(m, 5H), 7.00(d, J = 7.7 Hz, 1H), 6.88(t, J = 7.4 Hz, 1H), 6.74(d, J = 8.6 Hz , 1H), 6.24(s, 1H), 3.89~3.95(m, 1H), 3.62~3.78(m, 3H), 3.23~3.30(dd, 1H, J = 5.7 and 13.6 Hz, 1H), 1.22(s , J = 7.0 Hz, 3H); ESI-MS m / z: 401.0 [M+H] + ; Anal. calcd for C 19 h 17 BrN 2 o 3 (401.25): C56.87, H4.27, N6.98; found: C56.77, H3.94, N6.8.

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Abstract

The invention relates to the field of medicinal chemistry, and specifically relates 3-hydroxy-3-[2,3-dihydroquinoline-4-keto-3-yl]indole-2-ketone compounds (I) and pharmaceutically acceptable salts thereof or pharmaceutically acceptable solvent mixtures thereof, a preparation method thereof, and uses of the compounds in preparing medicaments for preventing or treating diseases related to abnormal cell proliferation, morphologic change and the like, in particular medicaments for preventing or treating tumor growth and transfer.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a class of 3-hydroxyl-3-[2,3-dihydroquinolin-4-one-3-yl]indol-2-one compounds with antitumor activity and their A pharmaceutically acceptable salt or a pharmaceutically acceptable solvate, a preparation method thereof, a pharmaceutical composition containing the compound, and the preparation of these compounds for preventing or treating diseases related to abnormal proliferation and morphological changes of cells, especially It is used in medicines for treating or preventing tumor growth and metastasis. Background technique [0002] Tumor is a common and frequently-occurring disease that seriously threatens human health. Statistics in the past ten years show that there are more than 10 million new cancer patients in the world every year, and the death rate caused by cancer is second only to heart and brain cancer. Vascular disease. The World Health Organization predicts that ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A61K31/4709A61P35/00
CPCC07D401/04
Inventor 张磊王京陈永正
Owner ZUNYI MEDICAL UNIVERSITY
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