摘要
4β-Azido-4-demethyl-4'-O-demethyl-epipedophyllotoxin reacted with phenyliodonium diacetate in MeOH at room temperature to synthesize a novel pedophyllotoxin derivative containing a cyclohexadienone group with the original configurations of C2 and C4, which are required for the antitumor activities. The component and structure of the pro-duct were confirmed using elemental analysis, high-resolution mass spectrum, ^1H and ^13C NMR spectra, and infrared spectrum. Furthermore, the fragmentation routes of the product were fully assigned with electron-impaet time-of-flight mass spectrometry( EI-TOF MS), which can also be used for the structural elucidation based on the molecular ion at m/z 455(16% ) and three novel characteristic fragment ions at m/z 183(37% ), 425(7% ), and 199(5% ). The cyclohexadienone product is sensitive to acidic media. When it is treated with a trace of acid, another novel derivative containing an orthoquinone moiety is formed, which links with the metabolism of the cancer inhihitors.
4β-Azido-4-demethyl-4'-O-demethyl-epipedophyllotoxin reacted with phenyliodonium diacetate in MeOH at room temperature to synthesize a novel pedophyllotoxin derivative containing a cyclohexadienone group with the original configurations of C2 and C4, which are required for the antitumor activities. The component and structure of the pro-duct were confirmed using elemental analysis, high-resolution mass spectrum, ^1H and ^13C NMR spectra, and infrared spectrum. Furthermore, the fragmentation routes of the product were fully assigned with electron-impaet time-of-flight mass spectrometry( EI-TOF MS), which can also be used for the structural elucidation based on the molecular ion at m/z 455(16% ) and three novel characteristic fragment ions at m/z 183(37% ), 425(7% ), and 199(5% ). The cyclohexadienone product is sensitive to acidic media. When it is treated with a trace of acid, another novel derivative containing an orthoquinone moiety is formed, which links with the metabolism of the cancer inhihitors.
基金
Supported by the National Nature Science Foundation of China(No.20202009).