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(5R)-5-hydroxyl triptolide derivative and preparation method and application thereof

A technology of lactone alcohol and derivatives, applied in the field of medicine, can solve problems such as toxicity reduction, and achieve the effect of reducing toxicity

Inactive Publication Date: 2019-11-05
FUJIAN ACAD OF MEDICAL SCI
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  • Application Information

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Problems solved by technology

[0003] Wang Dayuan et al. reported that thiocyanate was used to open the 12 and 13 epoxy to obtain triptolide thiocyanate lactone alcohol. Although this derivative is not easy to convert into triptolide, it is surprising that the compound has good Antitumor activity, and the toxicity of the compound is greatly reduced compared with triptolide

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  • (5R)-5-hydroxyl triptolide derivative and preparation method and application thereof
  • (5R)-5-hydroxyl triptolide derivative and preparation method and application thereof

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Embodiment 1

[0021] (5R)-5-Hydroxytripterygium thiocyanatolactoneol

[0022]

[0023] Preparation method: Add (5R)-5-hydroxytriptolide (126mg, 0.33mmol) into 15ml tert-butanol, stir at 80°C to dissolve (5R)-5-hydroxytriptolide. Ammonium thiocyanate (376 mg, 4.95 mmol) was then added to the reaction solution. Then the reaction solution was refluxed for reaction, and TLC was used to detect the reaction progress. After the reaction, 40ml of EtOAc was added to the reaction solution. The organic layer was washed three times with saturated NaCl aqueous solution, dried over anhydrous sodium sulfate, and filtered. Concentrate under reduced pressure, water bath temperature 55 ° C, to obtain a white solid, column chromatography, silica gel (40g, 200~300 mesh), with CH 2 Cl 2 / MeOH (100:1) was eluted, and the fractions were collected and dried in vacuo to obtain 82 mg of the product with a yield of 57%. mp: 248-250°C. Kedd's reagent was purple. 1 H NMR (400 MHz, DMSO- d 6 ) δ 6.35 (1s, 1H...

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Abstract

The invention provides a (5R)-5-hydroxyl triptolide derivative and a preparation method and application thereof. The structural formula of the (5R)-5-hydroxyl triptolide derivative is shown in the description, the (5R)-5-hydroxyl triptolide derivative is obtained by taking (5R)-5-hydroxyl triptolide and ammonium thiocyanate as raw materials through a heating reaction in an organic solvent. The (5R)-5-hydroxyl triptolide derivative has a potential to inhibit tumor cell proliferation.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to a specific chemical structure of a class of (5R)-5-hydroxytriptolide derivatives with antitumor activity and a preparation method thereof. Background technique [0002] A series of active triptolide derivatives were reported in a 2004 patent by Shanghai Institute of Materia Medica, Chinese Academy of Sciences. They tested the antitumor and immunosuppressive activity of this series of derivatives, and screened out the compound (5R)-5-hydroxytriptolide (LLDT-8). Then they conducted a systematic pharmacological study on LLDT-8. In vivo experimental animal models, intraperitoneal administration showed stronger immunosuppressive activity than CsA, and oral administration also had strong immunosuppressive activity. Existing results have confirmed that LLDT-8 has very significant immunosuppressive activity in experimental animal models in vivo, and its LD 50 It is 9.3mg / kg, indicating...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20A61P35/00
CPCA61P35/00C07D493/20
Inventor 李唯郭舜民阙慧卿陈阿虹林绥
Owner FUJIAN ACAD OF MEDICAL SCI
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