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Pseudomonoterpene indole alkaloid and its preparation method and application

A kind of pseudo-monoterpene indole biology, the technology of monoterpene indole biology, applied in the field of pseudo-monoterpene indole alkaloid and its preparation, can solve the problem of high toxicity and the like

Active Publication Date: 2020-03-31
THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the 1990s in our country, the phenanthrene and indole licidine alkaloids isolated by the laboratory of Professor Yu Shishan of the Chinese Academy of Medical Sciences had significant anti-tumor activity, but they failed to enter the clinic due to their high toxicity.

Method used

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  • Pseudomonoterpene indole alkaloid and its preparation method and application
  • Pseudomonoterpene indole alkaloid and its preparation method and application
  • Pseudomonoterpene indole alkaloid and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The preparation of embodiment 1 compound T1 comprises the following steps:

[0061] Step (1): Take 1.77mmol geniposide (geniposide) and put it into a 100mL dry round bottom flask, add 50mL dry tetrahydrofuran, then add activated manganese dioxide in batches, move to a 50°C oil bath and stir, the second Day treatment: filter (diatomaceous earth) to remove manganese dioxide and evaporate the solvent under reduced pressure, and the residue is separated by column chromatography (chloroform:methanol=10:1) to obtain the product M8.

[0062] Step (2): In the 100mL round bottom flask that 0.29mmol M8 is housed, add the H of 0.29mmol tryptamine hydrochloride and 0.14mmol tryptamine (Tryptamine) 2 O / AcOH (15mL / 0.73mL) solution, under nitrogen protection, was placed in an oil bath at 100°C and stirred overnight. The solvent was evaporated to dryness under reduced pressure, and the residue was separated by column chromatography (chloroform-methanol-diethylamine=200:20:1) and prepa...

Embodiment 2

[0064] The preparation of embodiment 2 compound T2 comprises the following steps:

[0065] Step (1): Weigh 0.88mmol of Genipin (Genipin), put it into a 25mL round bottom flask, add 4mL of absolute ethanol, then add a drop of concentrated hydrochloric acid, and stir at 60°C for 6h. 1 mol / L sodium hydroxide was added to the reaction solution to adjust the pH to 7, concentrated under reduced pressure, the residue was extracted with ethyl acetate, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was separated by silica gel column chromatography (petroleum ether-ethyl acetate=1:1) to obtain product M9.

[0066] Step (2): Take 3.93mmol M9 into a 250mL round bottom flask, add 30mL dry dichloromethane, add 2.27mmol Dess Martin oxidant (DMP) after dissolving, stir at room temperature for 1h, add saturated sodium bicarbonate, saturated thio Sodium sulfate aqueous solution, stir well. Th...

Embodiment 3

[0069] The preparation of embodiment 3 compound T3, comprises the following steps:

[0070] In a 10mL round bottom flask containing 0.13mmol 5-methoxytryptamine (M10A), add 0.13mmol 5-methoxytryptamine, 10mL ethanol, stir at room temperature for 1h, add a drop of concentrated hydrochloric acid, stir overnight, add saturated carbonic acid Sodium hydrogen aqueous solution to neutralize the acid, add water, extract with ethyl acetate, wash with water and saturated brine, dry over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and the residue is subjected to preparative thin-layer chromatography (ethyl acetate-methanol-di Ethylamine=100:1:1) to isolate the product T3.

[0071] The yield of compound T3 was 43.5%. ESI-MS m / z: 424.2[M+H] + ; 1 H-NMR (CDCl 3 , 400MHz) δ(ppm): 7.25(s, 1H), 7.50(s, 1H), 7.21(d, J=8.8Hz, 1H), 6.94(d, J=2.4Hz, 1H), 6.83(dd, J=8.8, 2.4Hz, 1H), 5.89(s, 1H), 5.01(s, 1H), 4.78(d, J=8.0Hz, 1H), 4.06-4.02(m, 1H), 3.86(s, 3H ), 3.7...

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Abstract

The invention discloses monoterpenoid indole alkaloid, which has a structural general formula shown as a formula (I). The invention also discloses a preparation method and application of the monoterpenoid indole alkaloid. The invention provides the monoterpenoid indole alkaloid as well as the preparation method and application of the monoterpenoid indole alkaloid. The monoterpenoid indole alkaloid provided by the invention has the characteristics of high efficiency and low toxicity. Compared with full synthesis of a natural product, the preparation method provided by the invention has the characteristics that simplicity is realized and the operation is easy. The goal can be achieved through one-step or several-step limited reaction; extreme reaction of high temperature, high pressure, strong acid and strong alkali does not exist; the reaction raw materials are simple and can be easily obtained; the method is suitable for mass industrial production. The obtained monoterpenoid indole alkaloid can be applied to anti-tumor medicine preparation. The formula (I) is shown in the specification.

Description

technical field [0001] The invention relates to a quasi-monoterpene indole alkaloid and a preparation method and application thereof, specifically belonging to the technical field of medicinal chemistry. Background technique [0002] Cancer is a common and frequently-occurring disease that seriously threatens human life, and its mortality rate is second only to cardiovascular diseases. According to the report of the World Health Organization, in 2000, there were about 10.06 million new cancer cases and 6.2 million deaths in the world. In 2005, the number of cancer deaths reached 7.6 million, accounting for 13% of the total number of 58 million deaths worldwide. It is estimated that by 2020, new cancers will be added. There will be 15 million patients and 10 million deaths, and more than 70% of all deaths will occur in low-middle-income and middle-income developing countries, and this proportion is rising rapidly. Cancer is becoming the number one killer of humans and one of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04C07H17/04C07H1/00C07D413/14C07D405/12C07D405/14C07D405/06C07D417/04C07D311/94A61K31/352A61K31/706A61K31/437A61K31/422A61K31/4045A61K31/405A61K31/404A61K31/427A61K31/513A61P35/00
CPCC07D311/94C07D405/06C07D405/12C07D405/14C07D413/14C07D417/04C07D471/04C07H1/00C07H17/04
Inventor 穆淑珍方家琪黄滔邓璐璐郝小江
Owner THE KEY LAB OF CHEM FOR NATURAL PROD OF GUIZHOU PROVINCE & CHINESE ACADEMY OF SCI
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