A kind of diterpene derivative and its preparation method, pharmaceutical composition and application

A technology of derivatives and compositions, applied in the field of diterpene derivatives and their preparation, can solve problems such as insufficient killing ability of cancer cells, and achieve the activity of effectively inhibiting the proliferation of various tumor cells, obvious anti-cancer activity, and the preparation process. Ease of use

Active Publication Date: 2022-03-01
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is no report on the antitumor activity of diterpene derivatives. For example, in the in vitro tumor cell proliferation test, pleuromutilin has insufficient killing ability to most cancer cells, and IC 50 Values ​​are greater than 100μM

Method used

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  • A kind of diterpene derivative and its preparation method, pharmaceutical composition and application
  • A kind of diterpene derivative and its preparation method, pharmaceutical composition and application
  • A kind of diterpene derivative and its preparation method, pharmaceutical composition and application

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Embodiment 1: Preparation of diterpene derivatives

[0040] (1) Preparation of compound 3:

[0041] The structure of compound 3 is as follows:

[0042] Its preparation process is as follows:

[0043] To a solution of pleuromutilin 1 (7.00 g, 22.1 B mmoL) in ethanol (50 mL) and water (32 mL) was added 50% aqueous sodium hydroxide (3.70 mL) at room temperature. After stirring at 65°C for 1 hour, the reaction mixture was cooled to room temperature and filtered, and the filtrate was acidified with 1N hydrochloric acid to pH=2, then diluted with ethyl acetate (200 mL); the organic phase was separated, and the aqueous phase was washed with ethyl acetate (3× 200 mL) for extraction; the combined organic phases were washed with saturated brine, dried over anhydrous sodium sulfate, concentrated in vacuo, and used directly for the next step.

[0044] To a solution of diol compound 2 (5.50 g, 17.2 mmol) in N,N-dimethylformamide (60 mL) was added tetramethylmethanediamine (60 m...

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PUM

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Abstract

The invention discloses a diterpene derivative and its preparation method, pharmaceutical composition and application. The structure of the diterpene derivative is shown in formula I, R 1 Oxygen, hydroxyl or ester group; R 2 Oxygen, hydroxyl or ester group; R 3 is ethyl or vinyl. The present invention obtains a novel diterpene derivative by means of semi-synthetic modification, the preparation process is simple and easy, and it is found through pharmacological experiments that the diterpene derivatives provided by the present invention all show strong activity of inhibiting the proliferation of various tumor cells , has obvious anticancer activity in vitro and in vivo, and generally does not have antibiotic activity, which is suitable for the development of antitumor drugs.

Description

technical field [0001] The invention belongs to the field of chemical medicine, and in particular relates to a diterpene derivative, a preparation method, a pharmaceutical composition and an application thereof. Background technique [0002] Diterpenoids are a class of natural products with complex and diverse structures and important biological activities. They are widely distributed in nature, plants, animals, and marine organisms. The molecular skeleton is composed of 4 isoprene units and contains 20 carbons. Compound classes of atoms. The structure shows diversity, the main types are kaurane, crotane, abietane, aconitane and so on. Many oxygen-containing derivatives of diterpenoids have various biological activities, and some are important drugs, such as paclitaxel, andrographolide, tanshinone, ginkgolide, triptolide, genkwa ester and stevia, etc. biological activity. [0003] At present, there is no report on the antitumor activity of diterpene derivatives. For examp...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/743C07C45/68C07C67/08C07C69/16C07C67/14C07C69/28C07C69/74C07C69/63C07C68/06C07C69/96C07C69/78C07C69/92C07C201/12C07C205/57C07D213/79C07D213/803C07C69/65C07C69/606C07C69/743C07C69/76A61K31/122A61K31/235A61K31/24A61K31/22A61K31/216A61K31/215A61P35/00A61P35/02A23L33/10
CPCC07C49/743C07C45/68C07C67/08C07C69/16C07C67/14C07C69/28C07C69/74C07C69/63C07C68/06C07C69/96C07C69/78C07C69/92C07C201/12C07C205/57C07D213/79C07D213/803C07C69/65C07C69/606C07C69/743C07C69/76A61P35/00A61P35/02A23L33/10C07B2200/07C07C2603/82C07C2601/04C07C2601/08C07C2601/02A23V2002/00A23V2200/308
Inventor 杨光张坤李辰
Owner NANKAI UNIV
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