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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Recent progress in marine natural products with 1,2-oxazine scaffold: structural diversity, biological potential and
Guifeng Ji1, Yanfeng Sun1, Xuanyi Xue1
1MOE Key Laboratory of Marine Drugs and Key Laboratory of Evolution and Marine Biodiversity, School of Medicine and Pharmacy, Institute of Evolution & Marine Biodiversity, Ocean University of China, Qingdao, 266003, China.
Abstract:
The 1,2-oxazine moiety, characterized by a directly linked N-O bond within a six-membered ring scaffold, benefits from the presence of oxygen and nitrogen heteroatoms to possess a high density of lone-pair electrons and a polarized ring system. These structural features optimize its physical properties and drug-likeness, thus rendering 1,2-oxazine a highly promising chemical scaffold for the discovery and development of bioactive lead compounds. Since the discovery of the first 1,2-oxazine-containing marine natural product (1,2-oxazine MNP) in 1986, a total of 56 naturally occurring 1,2-oxazine MNPs have been isolated and characterized. This review presents a systematic summary of the 1,2-oxazine MNP chemical family, with a primary focus on elaborating their source organisms, structural diversities, bioactivities, structure-activity relationship (SAR), mechanisms of action, chemical synthesis, and biosynthesis.
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