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Compound as well as preparation and application thereof

A technology for compounds and pharmaceutical preparations, applied in the field of new optical isomers and their preparations, can solve problems such as unreported

Active Publication Date: 2012-01-25
PAPANNA BEIJING TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although Panaxydol It has good biological activity, but there is no report on its different optical isomers and its synthesis and biological activity.

Method used

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  • Compound as well as preparation and application thereof
  • Compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation (3 S ,9 R ,10 R )-9,10-epoxy-1-heptadecen-4,6-diyn-3-ol

[0044] 0.0118g (0.12 mmol) cuprous chloride, 0.16mL n-butylamine, 0.37mL water, 0.108 g (0.6mmol) (4 R ,5 R )-4,5-epoxy-1-dodecyne in dichloromethane (9mL) solution was slowly added 0.144g (0.9mmol) ( S )-5-bromo-1-penten-4-yn-3-ol, 0.2081g (3mmol) hydroxylamine hydrochloride aqueous solution 2mL, keep the system light yellow, after the dropwise addition, continue to react for 1h. After the reaction, extract with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and perform silica gel column chromatography (petroleum ether: ether, 5:1) to obtain 0.13 g of light yellow oily liquid (yield: 85 %). [α] D 20 = 45.6 (c = 1.2, CHCl 3 ); 1 H NMR (300 MHz, CDCl 3 ): δ 5.95 (ddd, J = 17.03, 10.12, 5.33 Hz 1H), 5.43-5.50 (m, 1H), 5.23-5.27 (m, 1H), 4.90-4.94 (m, 1H), 2.81-2.88 (m, 2H), 2.67-2.75 ( m, 1H), 2.48-2.56 (m,1H), 1.97-1.99 (m, 1H), 1.25–...

Embodiment 2

[0047] Preparation (3 S ,9 R ,10 R )-9,10-epoxy-1-heptadecen-4,6-diyn-3-ol

[0048] 0.0177g (0.12 mmol) cuprous bromide, 0.16mL ethylamine, 0.37mL water, 0.108g (0.6mmol) (4 R ,5 R )-4,5-epoxy-1-dodecyne in chloroform (9mL) solution was slowly added 0.144g (0.9mmol) ( S )-5-bromo-1-penten-4-yn-3-ol, 0.2081g (3mmol) hydroxylamine hydrochloride aqueous solution 2mL, keep the system light yellow, after the dropwise addition, continue to react for 1h. After the reaction, extract with chloroform, combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and perform silica gel column chromatography (petroleum ether: ether, 5:1) to obtain 0.13 g of light yellow oily liquid (85% yield) . [α] D 20 = 45.6 (c = 1.2, CHCl 3 ); 1 H NMR (300 MHz, CDCl 3 ): δ 5.95 (ddd, J = 17.03, 10.12, 5.33 Hz 1H), 5.43-5.50 (m, 1H), 5.23-5.27 (m, 1H), 4.90-4.94 (m, 1H), 2.81-2.88 (m, 2H), 2.67-2.75 ( m, 1H), 2.48-2.56 (m,1H), 1.97-1.99 (m, 1H), 1.25–1.60 (m, 12H), ...

Embodiment 3

[0061] (4 R ,5 R The synthetic method of )-4,5-epoxy-1-dodecyne is

[0062] (1) Preparation of 2-decyn-1-alcohol (compound 2 )

[0063] Add 50mL tetrahydrofuran, 5.32mL (90mmol) propynyl alcohol, 39.5mL (225mmol) hexamethylphosphoric triamide to a 250mL reaction flask successively under nitrogen protection, and slowly add 72mL (180mmol) n-butyl at -78°C Lithium solution. After 0.5 h of dropwise addition, the temperature was raised to -30°C and stirred for 3 h, and 7.07 mL (45 mmol) of n-bromoheptane was added, stirred for 20 min, then raised to room temperature and continued to react for 21 h. After the reaction was completed, 30 mL of saturated ammonium chloride aqueous solution was added, extracted with ether (30 mL'3), and the organic phases were combined. The organic phase was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated. The crude product was subjected to silica gel (200-300 mesh) column chrom...

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Abstract

The invention belongs to the technical field of medicines and discloses a new compound (3S, 9R, 10R)-9,20-epoxy-1-heptadecene-4,6-diyne-3-alcohol. A pharmacological test shows that the compound disclosed by the invention has a better anticancer activity. The invention also discloses a synthesis method of the compound, and the synthesis method has the advantages of fewer reaction steps, mild reaction conditions, high yield, good stereoselectivity and the like.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a new class of optical isomers and their preparation and application. Background technique [0002] Natural polyynols mainly exist in plants such as Solanaceae, Platycodonaceae, Araliaceae, Pittogoniaceae, Oleaceae, Sandalaceae and Umbelliferae, and also have a certain distribution in Basidiomycetes. Studies have shown that polyacetylene alcohol compounds contained in ginseng have significant anti-inflammatory, anti-platelet aggregation, inhibition of cell oxidase, inhibition of leukemia cell growth, and inhibition of thrombosis. In addition, these polyacetylene alcohols extracted from Araliaceae It also has strong antitumor activity. [0003] Studies have shown that Panaxydol It has antihypertensive and anti-atherosclerosis and anti-cell proliferation activities. At the same time, some research groups have found that ginseng epoxy acetylenic alcohol also has anti-prolifera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/14C07D301/00A61K31/336A61P35/00
Inventor 王博
Owner PAPANNA BEIJING TECH