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Intermediate for preparation of bruguiesulfurol and synthetic method, intermediate and use thereof

A technology of sodium disulfide and compounds, which is applied in the field of preparation of oledithiol, can solve the problems of limited druggability and limited quantity, and achieve the effects of novel synthetic route, simple operation and high yield

Inactive Publication Date: 2014-11-12
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the amount that can be obtained by means of separation is limited, thus limiting the in-depth activity research and druggability evaluation of the compound

Method used

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  • Intermediate for preparation of bruguiesulfurol and synthetic method, intermediate and use thereof
  • Intermediate for preparation of bruguiesulfurol and synthetic method, intermediate and use thereof
  • Intermediate for preparation of bruguiesulfurol and synthetic method, intermediate and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: Synthesis of 1,3-dibromo-2-propanol (compound of formula IV)

[0049] Add 20 grams of epibromopropane (compound of formula V) into a three-necked bottle with a thermometer, cool down to below 0°C, slowly add 32 grams of hydrobromic acid (40%) dropwise, during the process of violent heat release, control the temperature below 5°C, after the addition was complete, keep stirring at 0°C for 4 hours, extract twice with ether, combine the organic phases, wash the organic phase with saturated aqueous sodium bicarbonate solution, and then wash the organic phase with water, dry the organic phase with anhydrous magnesium sulfate, filter and evaporate under reduced pressure The solvent was removed to obtain 27 g of a colorless oil (compound of formula IV), yield: 85%.

[0050] 1 H NMR (400MHz, CDCl 3 ): δ4.00(m,1H), 3.58(d,1H), 3.56(d,1H), 2.6(br,1H).

Embodiment 2

[0051] Example 2: Synthesis of 2-(1,3-dibromo-2-propoxy)-tetrahydropyran (compound of formula III)

[0052]1.09 g of 1,3-dibromo-2-propanol (compound of formula IV) was dissolved in 10 ml of tetrahydrofuran, then 0.84 g of 3,4-dihydropyran was added, followed by 125 mg of pyridine p-toluenesulfonate , stirred at room temperature for 2 hours, added 30 milliliters of ethyl acetate for dilution, washed twice with 30 milliliters of water, and then washed with 30 milliliters of saturated brine, the organic phase was dried over anhydrous sodium sulfate, concentrated by filtration, and the residue was washed with petroleum ether: ethyl acetate The ester (volume ratio 100:1) was used as the eluent, and 1.20 g of a colorless oil (compound of formula III) was obtained by silica gel column chromatography, with a yield of 80%.

[0053] 1 H NMR (400MHz, CDCl 3 ): δ4.76-4.79 (m, 1H), 3.88-4.04 (m, 2H), 3.51-3.71 (m, 5H), 1.53-1.87 (m, 6H).

Embodiment 3

[0054] Embodiment 3: the synthesis of formula II compound

[0055] Dissolve 2.85 grams of sodium sulfide nonahydrate in 10 milliliters of water, add 380 milligrams of sulfur powder, heat to 50 ° C, and wait until the sulfur powder is completely dissolved in the solution to obtain a light yellow solution, cool to room temperature, add this solution to the dissolved 1.20 grams In the chloroform solution of 30 milliliters of the compound of formula III, add a small amount of phase-transfer catalyst tetrabutylammonium bromide, the solution turns black, stir at room temperature for 12 hours, add 20 milliliters of water, separate layers, extract the aqueous layer with chloroform, combine the organic phases, Dry over anhydrous magnesium sulfate, filter, concentrate, and the residue uses petroleum ether:ethyl acetate (volume ratio 200:1) as the eluent, and obtains 500 mg of a colorless oil (compound of formula II) through silica gel column chromatography, Yield 61%.

[0056] 1 H NMR...

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Abstract

The present invention relates to a novel intermediate for preparation of bruguiesulfurol with II-type diabetes resisting activity, a synthetic method, an intermediate and use thereof, and a bruguiesulfurol preparation method. The bruguiesulfurol preparation method has the advantages of new synthetic route, simple operation, high yield and good safety, is suitable for industrialized production, and can solve the problem that in the prior art the compound only can be prepared form mangrove forest plant extracts by very-low-efficiency extraction and separation.

Description

technical field [0001] The present invention relates to the field of chemical synthesis, more specifically, the present invention relates to the preparation of novel intermediates of natural product bruguiesulfurol (bruguiesulfurol) with anti-type II diabetes activity, its synthetic method and its intermediates, and the preparation of new The method of ladenithiol. Background technique [0002] New clover dithiol is a five-membered ring disulfide compound with a new skeleton structure isolated from the mangrove plant clover (Phytochemistry2009, 70, 2096-2100), and its structural formula is as follows: [0003] (Formula I). [0004] Studies have shown that this compound has good inhibitory activity on type II diabetes target protein tyrosine phosphatase 1B (protein tyrosine phosphatase1B, PTP1B) (the inhibitory concentration is IC 50 =17.5μΜ), it has good application value in the treatment of type II diabetes and its complications. However, the amount that can be obtaine...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04C07D409/12
CPCY02P20/55C07D339/04C07D409/12
Inventor 郭跃伟沈旭陈静龚景旭陈莉莉
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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