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Tripterone 3-site modified derivative and application in preparation of antitumor drugs

A technology of begonia ketone and derivatives, applied to the 3-position modified derivative of begonia ketone and its application in the preparation of antitumor drugs, can solve the problems of unreported pharmacological activities and the like

Active Publication Date: 2020-12-22
TIANJIN NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, no specific pharmacological activity has been reported

Method used

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  • Tripterone 3-site modified derivative and application in preparation of antitumor drugs
  • Tripterone 3-site modified derivative and application in preparation of antitumor drugs
  • Tripterone 3-site modified derivative and application in preparation of antitumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of compound (IV)

[0050] Weigh 632mg (2.0mmol, 1.0eq) of begonia ketone in a reaction flask, add 4ml of pyridine to dissolve the sample, then add 667mg of triphenylchloromethane (2.4mmol, 1.2eq) and 293mg of dimethylaminopyridine (DMAP , 2.4mmol, 1.2eq). The reaction solution was stirred at room temperature overnight, and TLC detected that the reaction was complete. A large amount of pyridine was concentrated under reduced pressure, a large amount of dichloromethane was added to the residue for dilution, and the organic phase was washed successively with an equal volume of 10% citric acid water, saturated aqueous sodium bicarbonate solution, and saturated brine. The organic phase was dried and concentrated to obtain the crude compound (VI).

[0051] The crude compound (VI) was dissolved in 4ml of pyridine, and then 245mg of acetic anhydride (2.4mmol, 1.2eq) and 293mg of dimethylaminopyridine (DMAP, 2.4mmol, 1.2eq) were added to the reaction solution. The...

Embodiment 2

[0055] Preparation of compound (II)

[0056] Weigh 591mg of compound (IV) (1.65mmol, 1.0eq) in a reaction flask, add 5ml of anhydrous DMF to dissolve it, add 43.6mg of sodium hydride (1.82mmol, 1.1eq) to the reaction system and stir at room temperature for half After 1 hour, 147 mg of methoxymethyl chloride (1.82 mmol, 1.1 eq, MOMCl) was added to the reaction solution, and the reaction solution was stirred at room temperature, and the reaction was monitored by TLC to complete. Dichloromethane was added to the reaction solution to dilute the reaction solution, and the organic phase was washed successively with an equal volume of 10% citric acid water, saturated aqueous sodium bicarbonate solution and saturated brine. The organic phase was dried and concentrated to obtain the crude compound III.

[0057] The crude compound (III) was dissolved in tetrahydrofuran, 4N sodium hydroxide solution was added to the reaction solution, and stirred overnight at room temperature. TLC moni...

Embodiment 3

[0060] Preparation of compound (I-1)

[0061] Weigh 18 mg of compound (II) (1.0 equivalent) in the reaction flask, add 0.5 ml of methylene chloride in the reaction flask, add 1.1 equivalent of condensing agent EDCI, 1.1 equivalent of DMAP and 1.1 equivalent of carboxylic acid (RCOOH) under stirring at room temperature, and react The reaction was continued overnight at room temperature. TLC monitored the completion of the reaction. A large amount of dichloromethane was added to the reaction solution to dilute the reaction solution, and then the organic phase was washed with saturated aqueous sodium bicarbonate and saturated brine. The organic phase was dried, filtered, and concentrated to obtain the crude product. The crude product from the previous step was dissolved in 0.5 ml tetrahydrofuran, then 1N dilute hydrochloric acid was added, and reacted overnight at room temperature. TLC monitored the completion of the reaction. A large amount of dichloromethane was added to th...

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Abstract

The invention provides a tripterone 3-site modified derivative and application in preparation of antitumor drugs, wherein the structure of the tripterone 3-site modified derivative is shown as a formula (I), X is selected from or R'-(I-2), R is selected from C1-C4 saturated alkyl, allyl, phenyl, 4-chlorphenyl, 4-methylphenyl, 4-hydroxyphenyl, 4-cyanophenyl, 4-nitrophenyl, 4-methoxyphenyl and 4-trifluoromethylphenyl, and R' is selected from methyl, ethyl and benzyl. The invention also provides an application of any one tripterone 3-site modified derivative in preparation of antitumor drugs.

Description

technical field [0001] The invention relates to an abietane type diterpenoid compound and its application in the preparation of medicines. Background technique [0002] Kunming mountain crabapple (Tripterygium hypoglaucum Hutch) is a plant of the genus Tripterygium wilfordii in the family Euonymus, and its rhizome is mostly used as medicine. There are a variety of abietane-type diterpenoids in its medicinal parts, and there are certain Chinese literature on its anti-tumor activity in the prior art reports——Studies on the chemical components of the rhizome of Begonia Kunming (Song Qiang, etc., Journal of Chinese Herbal Medicine, November 2019, 5395-5399) disclosed an abietane-type diterpenoid——3β-hydroxyl-4 hydroxymethyl-astosin-8,11,13-triene-7-one (in this document Named Begonia ketone), its structural formula is as follows: [0003] However, its specific pharmacological activity has not been reported. The 3-position of begonia ketone is a β-hydroxyl group. In the re...

Claims

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Application Information

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IPC IPC(8): C07C69/157C07C69/16C07C69/54C07C69/78C07C69/84C07C255/57C07C205/57C07C69/92A61P35/00
CPCC07C69/157C07C69/16C07C69/54C07C69/78C07C69/84C07C255/57C07C205/57C07C69/92A61P35/00C07C2603/26Y02P20/55
Inventor 李西川周晓涛张春泽
Owner TIANJIN NORMAL UNIVERSITY
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