The synthetic method of harringtonine C ring intermediate

A technology of harringtonine and intermediates, which is applied in the field of synthesis of pharmaceutical intermediates, can solve the problems of expensive raw materials, environmental pollution, long routes and the like, and achieves the effect of simple operation
CN104045645BActive Publication Date: 2018-10-19HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
Publication Date
2018-10-19

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Abstract

The invention relates to an artificial synthetic method of a harringtonine C-ring intermediate. According to the method, 3,4-methylenedioxyphenethylamine (compound I) as a raw material is subjected to acylation in alkaline conditions to obtain N-acylated-3,4-methylenedioxyphenethylamine (compound II), which is then reacts with halogenated acetic acid or halogenated acetic acid derivative to generate N-acylated-3,4-methylenedioxyphenethylamine acetic acid (compound III); and the compound (III) is catalyzed by Lewis acid to generate intramolecular Friedel-crafts acylation reaction to obtain N-acyl-3,4-metheneoxybenzo-3-N-cycloheptanone, namely C ring of harringtonine. In the preparation process, products of each step are purified by washing and recrystallization; and the method has simple operation, total yield of 87.4%, and good industrial prospect.
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Description

technical field

[0001] The invention relates to a method for synthesizing a drug intermediate, in particular to a method for synthesizing an intermediate containing a C ring of harringtonine. Background technique

[0002] Horringtonine is a kind of alkaloid extracted from the plant of the genus Spicera, which has good anticancer activity and is mainly used clinically for the treatment of acute myeloid leukemia, acute monocytic leukemia, promyelocytic leukemia, and promyelocytic leukemia. Cell leukemia, chronic myelogenous leukemia and polycythemia vera and other diseases, also have a certain therapeutic effect on lymphoma.

[0003] At present, the harringtonine drugs used clinically are all extracted from plants, because the harringtonine plant resources are limited, the growth cycle is long, and the content of ester alkaloids with anticancer activity in plants is extremely low (per 100g The total alkaloid content in the cloverleaf branches and leaves is only 0.39%). If a l...

Claims

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