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
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  • Summary
  • Abstract
  • Description
  • Claims
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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.

Method used

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  • A kind of synthetic method of active alkaloid misszrtlide
  • A kind of synthetic method of active alkaloid misszrtlide

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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...

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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

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Application Information

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IPC IPC(8): C07D209/24
Inventor 周荣徐石海冯鹏举廖小建赵冰心
Owner JINAN UNIVERSITY
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