Preparation method of anticancer drug lanosterol derivative

Abstract

The invention belongs to the technical field of drug synthesis, and relates to a preparation method of a novel anticancer drug lanosterol derivative. According to the method, an intermediate LD-a is generated by taking lanosterol as a starting raw material under the protection of tert-butyl dimethyl silicon (TBS); a Sharpless asymmetric dihydroxylation reaction is carried out on the intermediate LD-a under the action of osmium tetroxide (OsO4), and a vicinal diol compound LD-b is generated; Swern oxidation is carried out on the LD-b compound under the a triethylamine alkaline condition, and aalpha-hydroxy-ketone compound LD-c is generated; an acylation reaction is carried out on the LD-c with acetic anhydride, and an intermediate LD-d is obtained; the intermediate LD-d is subjected to TBSremoval protection, and an intermediate LD-e is obtained; and finally, the target lanosterol derivative LD is obtained through epoxidation. According to the invention, the reaction conditions of allthe steps are relatively mild, the synthetic steps are short, the use of highly toxic or expensive reagents is avoided, the prepared product is high in purity, and the preparation method can be applied to industrial production.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a method for synthesizing novel lanosterol derivatives that can be used for treating cancer. technical background [0002] The study found that lanosterol may be able to prevent the aggregation of proteins that lead to cataracts. In experiments, lanosterol was used to treat the lens of dogs, rabbits, and humans. It was found that the turbidity of the lens and the volume of cataracts were reduced, the symptoms were relieved, and the vision became clearer. Eye drops containing lanosterol have been shown to be an effective treatment for cataracts. This research result has brought good news to those cataract patients who cannot take surgery. Lanosterol can be prepared from chain-like squalene ring closure, and a large amount of lanosterol needs to be extracted from the unsaponifiable matter in lanolin. Due to the special skeleton structure of lanosterol tetracyclic triterpenes, it is o...

AI Technical Summary

Problems solved by technology

[0006] This method also uses lanosterol as a raw material to obtain LD through upprotection, dihydroxylation, oxidation, epoxidation, acylation, and deprotection. However, the reaction time of this system is long, the yield is not high, and the amount of synthesis is small. And the repeated use of heavy metal catalysts is not conducive to industrial production and meets the requirements of clinical medicine

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