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Indole-3-carboxaldehyde isobutyryl hydrazone derivatives and preparation method thereof

A technology of indole derivatives and compounds, which is applied in the field of indole-3-formaldehyde isobutyryl hydrazone derivatives and its preparation, and can solve problems such as tumor recurrence, drug insensitivity, and tumor cells prone to drug resistance

Inactive Publication Date: 2012-08-08
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still many defects in its clinical application, such as tumor quiescent cells are not sensitive to drugs, after drug withdrawal, tumor quiescent cells re-enter the proliferation cycle, causing tumor recurrence, tumor cells are prone to drug resistance, etc.

Method used

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  • Indole-3-carboxaldehyde isobutyryl hydrazone derivatives and preparation method thereof
  • Indole-3-carboxaldehyde isobutyryl hydrazone derivatives and preparation method thereof
  • Indole-3-carboxaldehyde isobutyryl hydrazone derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 0.88g of 5-methoxyindole-3-carbaldehyde, 0.52g of isobutyrhydrazide and 30ml of anhydrous methanol into a 100ml three-necked flask, slowly raise the temperature to 60°C under stirring, keep the temperature for 12h, filter with suction, and filter cake After drying, it was recrystallized with acetone to obtain white crystals, and compound 1 was obtained after vacuum drying with a yield of 63.81%. MS (ESP) m / z: 259 (M);

[0026] Elemental analysis (C 14 h 17 N 3 o 2 ): %C: 64.72 (64.85); %H: 6.49 (6.61); %N: 16.48 (16.20); %O: 12.57 (12.34) (calculated values ​​in brackets)

[0027] NMR analysis (NMR spectrum see figure 1 ):

[0028] atomic number 1 2 3 4 5 6 7 8 9 10 δ / 1 H, ppm 11.22 10.66 7.52 3.64 6.70 7.18 8.20 3.18 7.56 1.01 Proton number 1 1 1 3 1 1 1 1 1 6 split fraction d d d s m m d m m m

[0029] s: singlet; d: doublet; m: multiplet.

Embodiment 2

[0031] Add 1.61g of 5-oxindole-3-carbaldehyde, 1.38g of isobutyrhydrazide and 70ml of absolute ethanol into a 100ml three-necked flask, slowly heat up to 50°C under stirring, keep the temperature for 9 hours, filter with suction, and dry the filter cake White crystals were obtained by recrystallization from ethyl acetate, and compound 2 was obtained after vacuum drying with a yield of 63.06%. MS (ESP) m / z: 245 (M);

[0032] Elemental analysis (C 13 h 15 N 3 o 2 ): %C: 63.52 (63.66); %H: 6.09 (6.16); %N: 17.38 (17.13); %O: 13.19 (13.05) (calculated values ​​in brackets)

[0033] NMR analysis (NMR spectrum see figure 2 ):

[0034] atomic number 1 2 3 4 5 6 7 8 9 10 δ / 1 H, ppm 11.22 10.66 7.52 3.64 5.25 7.18 8.20 3.18 7.56 1.01 Proton number 1 1 1 3 1 1 1 1 1 6 split fraction d d d s m m d m m m

[0035] s: singlet; d: doublet; m: multiplet.

Embodiment 3

[0037] Add 1.79g of 5-chloroindole-3-carbaldehyde, 1.85g of isobutyrhydrazide and 30ml of anhydrous methanol into a 100ml three-necked flask, slowly raise the temperature to 45°C under stirring, keep the temperature for 12h, filter with suction, and dry the filter cake White crystals were obtained by recrystallization from petroleum ether, and compound 3 was obtained after vacuum drying with a yield of 61.75%. MS (ESP) m / z: 263 (M);

[0038] Elemental analysis (C 13 h 14 ClN 3O): %C: 59.48 (59.21); %H: 5.21 (5.35); %Cl: 13.56 (13.44); %N: 15.81 (15.93); %O: 6.14 (6.07) (calculated values ​​in brackets)

[0039] NMR analysis (NMR spectrum see image 3 ):

[0040] atomic number 1 2 3 4 5 6 7 8 9 δ / 1 H, ppm 7.00 10.10 7.30 7.10 7.60 7.50 7.30 2.78 1.19 Proton number 1 1 1 1 1 1 1 1 6 split fraction d d d s s s d m m

[0041] s: singlet; d: doublet; m: multiplet.

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PUM

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Abstract

The invention relates to a new class of indole derivatives and a preparation method thereof. The method comprises the steps of: taking indole-3-carboxaldehyde derivatives and isobutyryl hydrazine as raw materials, and partially or wholly introducing groups with anticancer activities such as -OCH3, -C=N-NH-C=O, and the like to proper positions of the indole derives through chemical reaction to obtain a series of indole compounds containing multiple functional groups. The technology is with simple operation, requires mild reaction conditions and has a high yield. Furthermore, the compounds havegood biological activities, can be used for tumour therapy and have a wide application prospect in a pharmaceutical field.

Description

technical field [0001] The invention relates to a new class of indole hydrazone derivatives and a preparation method thereof. The derivatives have excellent anticancer activity. Background technique [0002] Malignant tumors seriously threaten human life and health. Millions of patients die from malignant tumors every year in the world, accounting for about 1 / 4 of the total death toll. The treatment of malignant tumors is an urgent problem to be solved in clinical medicine, and it is also one of the main research topics in the field of biomedicine. Tumor treatment methods include surgery, radiation therapy, photodynamic therapy, immunotherapy, thermal therapy, and drug therapy, and drug therapy plays an important role in the comprehensive treatment of tumors. [0003] Indole compounds are a class of heterocyclic alkaloids with significant physiological activity. Especially the hydrazone with indole-3-carboxaldehyde as the parent showed obvious anticancer activity. In add...

Claims

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Application Information

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IPC IPC(8): C07D209/14A61P35/00
Inventor 卜娟段洪东王兴建秦大伟孟霞
Owner QILU UNIV OF TECH
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