Okadaic acid derivative and preparation method thereof

A technology of Datian soft sponge acid and derivatives, applied in the direction of organic chemistry, etc., can solve the problems of low total yield, long synthesis route and high difficulty, and achieve the effects of reducing the generation of by-products, fewer processes, and broad market prospects.

Inactive Publication Date: 2020-03-24
深圳市齐盛伟生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The synthesis method of okadaic acid or its fragments is found in the following documents, but due to the long synthetic route, high difficulty and low total yield, it cannot be widely used in the preparation of samples
So far, there is no information about new okadaic acid derivatives, such as benzyl okadaic acid, 2,7,24,27-tetrabenzoyl okadaic acid, 2,7,24,27-tetra Propionyl okadaic acid etc., report on its preparation method

Method used

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  • Okadaic acid derivative and preparation method thereof
  • Okadaic acid derivative and preparation method thereof
  • Okadaic acid derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0027] Benzyl esterification of okadaic acid to prepare compound 1;

[0028] Procedure: Add 2.4mg okadaic acid, 5mg K to a 25mL round bottom flask 2 CO 3 and 4 mL of anhydrous acetone, take 2 drops of benzyl bromide and dissolve in 1 mL of anhydrous acetone in a constant pressure dropping funnel, stir in an ice-water bath for 1 hour, then slowly drop into the reaction flask; stir overnight at room temperature. Add 5 mL of ice water, neutralize with 0.5M HCl, extract with ethyl acetate (3 mL×3), and wash with saturated brine. The organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the crude product was subjected to flash silica gel column chromatography (chloroform:methanol=30:1) to obtain 2.3 mg of compound 1: light brown amorphous solid, yield 86%.

Embodiment 2

[0030] Compound 2 was prepared by benzoylation of okadaic acid;

[0031] Procedure: 4.8 mg of okadaic acid, 2 drops of benzoyl chloride, 1 mg of DMAP and 2 mL of anhydrous pyridine were added to a 25 mL round bottom flask. Stir overnight at room temperature. Add 5 mL of ice water, extract with ethyl acetate (3 mL×3), wash with 1M HCl, and wash with saturated brine. The organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the crude product was subjected to flash silica gel column chromatography (chloroform:methanol=60:1) to obtain 4.8 mg of compound 2: light brown amorphous solid, yield 66%.

Embodiment 3

[0033] Propionylation of okadaic acid to prepare compound 3;

[0034] Procedure: 2.4 mg of okadaic acid, 2 drops of propionic anhydride, 0.5 mg of DMAP and 2 mL of anhydrous pyridine were added to a 25 mL round bottom flask. Stir overnight at room temperature. Add 5 mL of ice water, extract with ethyl acetate (3 mL×3), wash with 1M HCl, and wash with saturated brine. The organic layers were combined and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the crude product was subjected to flash silica gel column chromatography (chloroform:methanol=60:1) to obtain 2.2 mg of compound 3: a white amorphous solid, with a yield of 72%.

[0035]

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Abstract

The invention relates to the technical field of medicine preparation, particularly to an okadaic acid derivative and a preparation method thereof. According to the invention, the okadaic acid derivative prepared by the preparation method is high in yield and novel and coordination compound in structure; compared with the method in the prior art, the preparation method adopted by the invention is simple and practical, has few procedures, reduces the generation of byproducts, and improves the purity of the prepared okadaic acid derivative; and the okadaic acid derivative has potential application and wide market prospect in the field of pharmacy.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, in particular to an okadaic acid derivative and a preparation method thereof. Background technique [0002] Okadaic acid (OA) and its derivatives, dinophysistoxins-1 and 2 (DTX-1 and DTX-2) are the main components of diarrheal shellfish poisoning (DSP), and diarrhea Research status of shellfish poisoning The poisoning caused by it may not only endanger the ecological balance of the ocean, but also threaten human health through the enrichment of the marine food chain. Among them, the LD of DTX-1 50 and LD99 were 160 and 166 μg / kg respectively; while okadaic acid had an effect on the intraperitoneal injection of LD in mice 50 The harmful dose to the human body is 1.0-1.5 μg okadaic acid / kg body weight or 50 μg okadaic acid equivalent / person. Modern studies have shown that okadaic acid is a specific inhibitor of protein phosphatase PP1 and PP2A, which can induce apoptosis of various ...

Claims

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Application Information

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IPC IPC(8): C07D519/00
CPCC07D519/00
Inventor 罗维
Owner 深圳市齐盛伟生物科技有限公司
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