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Novel gossypol Schiff base derivative with antineoplastic activity and synthetic method thereof

A synthesis method and product technology, applied in the field of medicinal chemistry, can solve the problems of drug resistance, obvious bone marrow suppression, strong toxic and side effects, etc., and achieve the effects of high utilization rate, few reaction steps, and high operational safety.

Inactive Publication Date: 2018-01-12
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the chemotherapy drugs clinically used for malignant tumors have strong toxic and side effects and obvious bone marrow suppression, and drug resistance will gradually develop after long-term use. As a natural drug, gossypol has significant anti-tumor effects and has less side effects. Its metabolite oxidized gossypol also has significant anti-tumor effect

Method used

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  • Novel gossypol Schiff base derivative with antineoplastic activity and synthetic method thereof
  • Novel gossypol Schiff base derivative with antineoplastic activity and synthetic method thereof
  • Novel gossypol Schiff base derivative with antineoplastic activity and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Compound A dimethyl2,2'-(6,6'-((1Z,1'E)-((1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3, 3'-dimet hyl-[2,2'-binaphthalene]-8,8'-diyl)bis(methylidene))bis(azanylylidene))bis(3-imino-3H-xanthene-9,6-diyl)) dibenzoate and compound B(Z)-methyl2-(6-(((8'-formyl-1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'- Preparation of dimethyl-[2,2'-binaphthalen]-8-yl)methylene)amino)-3-imino-3H-xanthen-9-yl)be nzoate.

[0026]

[0027] Accurately weigh 103.71mg (0.2mmol) of gossypol acetate and 131.7mg (0.4mmol) of rhodamine 123 and dissolve them in 20mL of chloroform respectively, then mix them and place them in a round-bottomed flask, raise the temperature to 40°C under magnetic stirring, and react for 12 hours. Thin-layer chromatography tracked the reaction until it was complete, stopped heating, removed the condensing device, filtered the reaction solution after cooling to obtain the crude product of mixture A and B, added 25ml of acetone to the obtained crude product for rec...

Embodiment 2

[0035]Compound A dimethyl2,2'-(6,6'-((1Z,1'E)-((1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3, 3'-dimet hyl-[2,2'-binaphthalene]-8,8'-diyl)bis(methylidene))bis(azanylylidene))bis(3-imino-3H-xanthene-9,6-diyl)) dibenzoate and compound B(Z)-methyl2-(6-(((8'-formyl-1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'- Preparation of dimethyl-[2,2'-binaphthalen]-8-yl)methylene)amino)-3-imino-3H-xanthen-9-yl)be nzoate.

[0036]

[0037] Accurately weigh 103.71mg (0.2mmol) of gossypol acetate and 158.1mg (0.48mmol) of rhodamine 123 and dissolve them in 25mL of toluene respectively, then mix them and place them in a round bottom flask, raise the temperature to 60°C under magnetic stirring, and react for 12 hours. Thin-layer chromatography tracked the reaction until it was complete, stopped heating, removed the condensing device, filtered the reaction solution after cooling to obtain the crude product of mixture A and B, added 25ml of ethanol to the obtained crude product for recrysta...

Embodiment 3

[0039] Compound A dimethyl2,2'-(6,6'-((1Z,1'E)-((1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3, 3'-dimet hyl-[2,2'-binaphthalene]-8,8'-diyl)bis(methylidene))bis(azanylylidene))bis(3-imino-3H-xanthene-9,6-diyl)) dibenzoate and compound B(Z)-methyl2-(6-(((8'-formyl-1,1',6,6',7,7'-hexahydroxy-5,5'-diisopropyl-3,3'- Preparation of dimethyl-[2,2'-binaphthalen]-8-yl)methylene)amino)-3-imino-3H-xanthen-9-yl)be nzoate.

[0040]

[0041] Accurately weigh 103.71mg (0.2mmol) of gossypol acetate and 168.1mg (0.5mmol) of rhodamine 123 and dissolve them in 25mL of ethyl acetate respectively, then mix them and place them in a round bottom flask, raise the temperature to 60°C under magnetic stirring, and react for 12 hours . Thin-layer chromatography tracked the reaction until it was complete, stopped heating, removed the condensing device, filtered the reaction solution after cooling to obtain the crude product of mixture A and B, added 25ml of acetone to the obtained crude product for ...

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Abstract

The invention discloses a novel gossypol Schiff base derivative with antineoplastic activity and a synthetic method thereof. The compound uses Rhodamine 123 and gossypol acetate as starting materialsto react in a non-polar organic solvent, a crude product is obtained after the reaction ends, and Schiff base compound A and compound B are obtained through recrystallization and silica gel column chromatography isolation. The method is few in reaction steps, mild in reaction condition and high in raw material utilization rate, and is applicable for industrial production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to the structure and synthesis method of a novel gossypol Schiff base derivative with antitumor activity. Background technique [0002] Rhodamine 123 (Rh 123) is a commonly used cationic green fluorescent dye, which can permeate the cell membrane to accumulate in the mitochondria of living cells and emit yellow-green fluorescence. It is used as a fluorescent probe for detecting mitochondrial membrane potential and has no effect on cells. any toxicity. As a commonly used biological dyeing material, some studies have confirmed that rhodamine 123 itself has certain cytotoxicity, and it is widely used in cancer research such as: liver cancer, bladder cancer, pancreatic cancer, etc., through its fluorescence in cancer cells Distribution to analyze the changes in cancer cells under the action of drugs is of great significance for cancer research. [0003] Gossypol, as a sesquiterpene ...

Claims

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Application Information

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IPC IPC(8): C07D311/82A61P35/00
Inventor 梁承远田蕾鞠星可谢晓林张德柱
Owner SHAANXI UNIV OF SCI & TECH
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