Skeleton Synthesis of a Plant-Derived Radioprotective Alkaloid Born to Produce a Novel Fused Heterocycle

Alkaloids are a material treasure bestowed on humans by nature owing to their numerous biological activities. Orychophragine D, an alkaloid isolated from the seeds of was identified as bearing a novel skeleton and proved to have an excellent radioprotective effect. Different from the common alkaloid...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2023-04, Vol.28 (9), p.3829
Main Authors: Liu, Sifan, Gu, Huiling, Liang, Kai, Wei, Zhenzhen, Li, Bin, Tian, Ying, Li, Ruihong, Zhang, Guangjie, Liu, Shuchen
Format: Article
Language:English
Subjects:
Acids
alkaloid
Alkaloids
Alkaloids - chemistry
Alkaloids - pharmacology
Antineoplastic Agents
Binding Sites
chemical synthesis
Chromatography
Gases industry
Humans
Hydroxyl groups
International economic relations
L-Serine
Molecular Structure
novel molecular skeleton
orychophragine D
Plants
Seeds
Skeleton
Solvents
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Summary:Alkaloids are a material treasure bestowed on humans by nature owing to their numerous biological activities. Orychophragine D, an alkaloid isolated from the seeds of was identified as bearing a novel skeleton and proved to have an excellent radioprotective effect. Different from the common alkaloid structure, the main block of orychophragine D is constructed of an oxotriazine and an oxopiperazine, which are connected in parallel by a C-N bond. In this paper, a preparation method for the novel heterocycle skeleton of orychophragine D is proposed for the first time. N-Boc-L-serine was utilized as the original material to complete the preparation with 11 steps in a 13% overall yield. A hydroxyl group was established on the side chain of the skeleton as the reaction site for researchers to conduct further structural modification or derivatization.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28093829