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Method for synthesizing Benastatin J

A technology of benastatin and synthetic route, which is applied in the field of medicinal chemical synthesis, and can solve problems such as complex chemical structure and difficulty in chemically synthesizing benastatin J

Active Publication Date: 2018-07-06
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] As a new type of natural statin drug, benastatin J has broad application prospects, but due to the complex chemical structure of benastatin J, it is difficult to chemically synthesize benastatin J, and the preparation of benastatin J is usually from the chain Benastatin G was isolated from the fungus, and then benastatin G was transformed into benastatin J through methylation and elimination of a molecule of water. There is no report on the chemical synthesis of benastatin J.

Method used

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  • Method for synthesizing Benastatin J
  • Method for synthesizing Benastatin J
  • Method for synthesizing Benastatin J

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0113] Embodiment 1: Compound shown in preparation formula 3:

[0114] Step a: prepare the compound shown in formula 8:

[0115]

[0116] The compound of formula 7 (3.51g, 19.49mmol) was dissolved in N,N-dimethylformamide (20mL), and then phosphorus oxychloride (2.68mL, 29.23mmol) was slowly added dropwise at 0°C under nitrogen protection, After the dropwise addition, stir the reaction at 90°C for 3 hours to end the reaction. After the reaction solution is cooled to room temperature, it is slowly poured into ice water. The resulting mixed solution is adjusted to pH 10 with 20 wt% sodium hydroxide solution, and then extracted with ether. , the organic phases were combined, and the organic phase obtained was washed once with saturated sodium bicarbonate solution and saturated brine successively, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure until no solution was distilled off, and the residue was analyzed by column chr...

Embodiment 2

[0144] Embodiment 2 prepares the compound shown in formula 4:

[0145] Step A: prepare the compound shown in formula 14:

[0146]

[0147] The compound of formula 13 (8.08g, 25.58mmol) was dissolved in N,N-dimethylformamide (64mL), and potassium carbonate (7.78g, 56.27mmol) and dimethyl sulfate (5.09mL, 53.72mmol) were added, Then react at 60°C for 21.5 hours to end the reaction, cool the reaction liquid to room temperature, quench with saturated ammonium chloride solution, extract with ethyl acetate, combine the organic phases, and wash the organic phases twice with water, saturated chlorinated Sodium was washed once, dried with anhydrous sodium sulfate, filtered, concentrated, and the residue was separated by column chromatography (5% ethyl acetate / petroleum ether) to obtain the compound of formula 14 (7.74g, yield rate 88%), Rf= 0.56 (20% ethyl acetate / petroleum ether).

[0148] Tested: 1 H NMR (300MHz, CDCl 3 )δ6.46(s,2H),3.91(s,6H),3.83(s,3H)ppm;

[0149] 13 C NM...

Embodiment 3

[0193] Embodiment 3 prepares the compound shown in formula 1:

[0194] Step ①: prepare the compound shown in formula 5:

[0195]

[0196] The compound of formula 3 (907mg, 2.07mmol) was dissolved in a mixed solvent of N,N-dimethylformamide (5mL) and diisopropylamine (3mL), and tetrakistriphenylphosphine palladium (239.2mg, 0.207mmol) was added , cuprous iodide (19.7mg, 0.104mmol), after freezing and deoxygenating with liquid nitrogen, add 2.5mL of N, N-dimethylformamide solution of formula 4 compound (496.2mg, 2.17mmol) of freezing and deoxygenating, and then React at 45°C for 3 hours to end the reaction. After cooling the reaction liquid to room temperature, add saturated ammonium chloride to quench, extract with ethyl acetate, combine the organic phases, wash the obtained organic phases twice with distilled water, and then with saturated sodium chloride. Once, dried over anhydrous sodium sulfate, filtered, concentrated, and the residue was separated by column chromatogra...

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Abstract

The invention discloses a method for synthesizing Benastatin J. The method comprises step (2) or step (1) in the following synthetic route shown in the description, wherein R1 and R2 are separately selected from C1 to C8 alkyl. By adopting the method, the chemical synthesis of the Benastatin J is firstly realized, a high practical value for realizing the industrialized preparation of the Benastatin J can be realized, the preparation method disclosed by the invention has the advantages of simple operation, safety, no pollution, no special requirement on devices, low production cost and the like, and has important significance for realizing the mass production.

Description

technical field [0001] The invention relates to a method for synthesizing benastatin J, which belongs to the technical field of pharmaceutical chemical synthesis. Background technique [0002] Benastatin (Benastatin) is a new type of natural drug, the more mature benastatin compounds are Benastatin A (Benastatin A, CAS#138968-85-1), Benastatin B (Benastatin B , CAS#138968-86-2), Benastatin C (Benastatin C, CAS#150151-88-5), Benastatin D (Benastatin D, CAS#150151-89-6), etc. [0003] Christian Hertweck et al. isolated several new benastatin compounds, including benastatin G and benastatin J, and found that: benastatin G showed good biological activity on human cervical cancer cells, and its IC50 The structural formulas of benastatin G and benastatin J are as follows: [0004] [0005] As a new type of natural statin drug, benastatin J has broad application prospects, but due to the complex chemical structure of benastatin J, it is difficult to chemically synthesize benas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/78
CPCC07D311/78
Inventor 辛坤云陈彦宇杨鲍潮高栓虎
Owner EAST CHINA NORMAL UNIV
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