Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of synthetic method of active alkaloid misszrtlide

A technology of active alkaloid and synthesis method, which is applied in the field of synthesis of active indole alkaloid Misszrtlide, can solve the problems of inability to meet actual clinical research and industrial application requirements, less difficulty in collecting alkaloids, etc., so as to reduce synthesis time and Purification process, improved yield and control of by-products, the effect of broad market prospects

Inactive Publication Date: 2019-09-17
JINAN UNIVERSITY
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the amount of alkaloids isolated in nature is very small and difficult to collect, it is far from meeting the needs of actual clinical research and industrial application. Therefore, a cost-effective, artificial, and environmentally friendly path to solve marine alkaloids is sought. The source of medicines has become one of the urgent issues nowadays

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of synthetic method of active alkaloid misszrtlide
  • A kind of synthetic method of active alkaloid misszrtlide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: the synthesis of active alkaloid Misszrtlide

[0046] (1) Coupling of amides

[0047] In a 250 mL round bottom flask, 4.0 g of L-phenyllactic acid (L-(-)-3-Phenyllactic acid, 24 mmol) was dissolved in 100 mL of dry dichloromethane (DCM), and then 3.8 g of 1- (3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 20mmol) was reacted for 5min, then 2.7g of 1-hydroxybenzotriazole (HOBt, 20mmol) was added and stirred for 60min Afterwards, 5.1 g of L-tryptophan methyl ester hydrochloride (H-Trp-OMe HCl, 20 mmol) was added thereto, nitrogen gas was introduced, and the reaction was carried out at room temperature (25-29° C.) for 30 h, and thin-layer chromatography ( TLC) follow the reaction, after the reaction is complete, spin dry under reduced pressure, extract three times with dichloromethane (DCM) and water, lyophilize the organic phase, and then separate through column chromatography to obtain N α -((R)-2-Hydroxy-phenylpropionyl)-L-tryptophan met...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of alkaloid and discloses a method for synthesizing active alkaloid Misszrtlide and an analogue thereof. The method comprises the following steps: adopting chiral raw materials, namely L-methyl tryptophan hydrochloride and L-phenyl lactic acid as substrates and performing non-racemic amide connection under the condition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / 1-hydroxybenzotriazole; subsequently reacting with tert-butyldimethylsilyl chloride under imidazole conditions, so that hydroxyl is promoted, and the competition with N-H on tryptophan indole in the process of reaction with R1Br (R1 can be one of 3,3-dimethylpropenyl, p-toluoyl and decanoyl) under alkaline conditions in the next step is avoided; finally, mildly and efficientlyremoving the tert-butyldimethylsilyl protection with a hydrogen fluoride pyridine solution to obtain the Misszrtlide or the analogue thereof with high yield and easiness in processing through four-step reaction. The method disclosed by the invention is simple, low in raw material cost, mild in reaction conditions, high in purity and easy to industrialize and has wide market prospect.

Description

technical field [0001] The invention belongs to the field of alkaloids, in particular to a method for synthesizing active indole alkaloid Misszrtlide. Background technique [0002] The ocean is a huge treasure trove of natural medicines, especially the alkaloids, which are a class of basic secondary compounds synthesized from different amino acids or their direct derivatives containing amide groups and other complex carbon skeleton ring structures. Metabolites. It exhibits good antitumor, antiviral, antibacterial and enzyme inhibitory activities in vivo. Umezawa in Japan isolated an exopolysaccharide marinactin, which has a strong inhibitory effect on tumor cells, from a strain of marine bacteria. It is currently on the market in Japan as an adjuvant for the treatment of tumors. Scholars in my country also isolated prodigiosin—Prodigiosin from the metabolites of bacteria Pseudomonas sp., and first developed it as a natural color and antibiotic. (Wei Chengli, Li Ling. Rese...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D209/24
Inventor 周荣徐石海冯鹏举廖小建赵冰心
Owner JINAN UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com