Gronwell naphthaquinone derivative and its application in preparing anticancer medicine

A technology of naphthoquinones and derivatives is applied to naphthoquinone derivatives of shikonen and its application field in the preparation of anticancer drugs, and can solve the problem of insufficient antitumor activity and high

Inactive Publication Date: 2002-10-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Just because their antitumor activity is not high enough, still can't be used clinically [Institute of Materia Medica, Chinese Academy of Medical Sciences, Modern Research on Chinese Herbal Medicine (Volume Two), p274, 1996, Beijing Medical University-China Union Medical University Press ]

Method used

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  • Gronwell naphthaquinone derivative and its application in preparing anticancer medicine

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Embodiment 1

[0022] The present invention will be further illustrated by the following examples. Example 1: Extraction, separation and purification of shikonin compounds

[0023] Shikonin compounds [R 1 =OH, (CH 3 ) 2 C=CHCOO, CH 3 COO or CH 3 COOC(CH 3 ) 2 CH 2 COO, R 2 =R 3 =H] The configuration is R-type, and the content is higher in Onosma confertum W.W. Smith.

[0024]Weigh 5 kg of Sichuan Lithospermum erythrorhizon, grind it through a 20-mesh sieve, and perform percolation extraction at room temperature with 95% ethanol until it is nearly colorless. The extracts were combined, concentrated under reduced pressure, and 2% NaOH equivalent to 1 / 3 to 1 / 2 of the volume of the concentrated solution was added to the concentrated solution, and the solution changed from purple-red to blue. After filtering to remove the insoluble matter, it was acidified by adding concentrated HCl. At this time, the solution changed from blue to purple-red, and a large amount of precipitate was formed at the same t...

Embodiment 2

[0024]Weigh 5 kg of Sichuan Lithospermum erythrorhizon, grind it through a 20-mesh sieve, and perform percolation extraction at room temperature with 95% ethanol until it is nearly colorless. The extracts were combined, concentrated under reduced pressure, and 2% NaOH equivalent to 1 / 3 to 1 / 2 of the volume of the concentrated solution was added to the concentrated solution, and the solution changed from purple-red to blue. After filtering to remove the insoluble matter, it was acidified by adding concentrated HCl. At this time, the solution changed from blue to purple-red, and a large amount of precipitate was formed at the same time. Let it stand overnight. The precipitate was filtered out and washed with distilled water to near neutral. The precipitate was dried to obtain about 60 g of a powdery solid crude product. Dissolve the crude product with dichloromethane, add appropriate amount of silica gel and stir evenly, and then evaporate to dryness before loading on the column. Th...

Embodiment 3

[0027] A methanol solution (8 mL) of 0.2 mmol β, β-dimethylacryloylakineine and 1 mmol aniline was stirred for reaction at room temperature for 6 days, and the reaction was followed by TLC. After the completion of the reaction, the solvent was removed under reduced pressure, and the crude product was separated by flash column chromatography (using petroleum ether-ethyl acetate as the eluent) to obtain a product in which the hydrogen at C-7 or C-8 was replaced by an arylamino group ( 9, 10), the total yield is about 80%. Using the same method, using β, β-dimethylacryloyl akanin as a raw material, compounds 11 and 12 can be synthesized. Embodiment four: R 1 Is substituted aniline, R 2 Or R 3 Synthesis of Shikonoquinone Derivatives Substituted for Phenylamino

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Abstract

The present invention relates to the gromwell naphthoquinone derivative and its application in preparing anticancer medicine. Experiment shows that the gromwell naphthoquinone derivative has obvious inhibition to tumor cell strain CNE2, Glc-82, S180A, EAC, HepA, etc, and the research on nude mouse transplantation tumor model of human cancer cell also proves the anticancer action of the gromwell naphthaquinone derivative.

Description

Technical field [0001] The present invention relates to a class of shikonin naphthoquinone derivatives and their use in preparing medicines for treating cancer. technical background [0002] Cancer is currently one of the most harmful diseases to human health and quality of life. The development of anticancer drugs has always been a hot topic for scientists. Due to the complexity and particularity of the mechanism of cancer, the search for anticancer drugs with high selectivity, high efficiency, low toxicity and small side effects has not achieved ideal results. [0003] The naphthoquinone compounds contained in a variety of traditional Chinese medicines have been found to have certain anti-tumor activities. For example, β-hydroxyisovaleryl shikonin isolated from the root of Lithospermum erythrorhizon can induce apoptosis of leukemia HL-60 cells; β, β- Dimethacryloylakine has an inhibitory effect on human prostate cancer cells (DU145, LNCaD, PC-3); Xinjiang shikonin has an inhibi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/122A61K31/135A61P35/00C07C50/32C07C69/007C07C225/30C07C323/22
Inventor 古练权刘宗潮黄志纾段志芳马林谢冰芬朱孝峰
Owner SUN YAT SEN UNIV
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