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1. The Synthesis Of α-Asarone 2. Study On Synthesis And Biologic Activity Of Harmine Derivatives

Posted on:2008-01-17Degree:MasterType:Thesis
Country:ChinaCandidate:Y ZhouFull Text:PDF
GTID:2121360215487221Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
The dissertation work includes two parts:1. An efficient and simple synthesis ofα-asarone was developed. The mixtureofα- andβ-asarone was synthesized by the Wittig reaction of2,4,5-trimethoxybenzaldehyde with ethyltriphenylphosphonium bromide, followedby isomerization to afford pureα-asarone by bis(acetonitrile) palladium(Ⅱ) chloridewithout separation. The effect of reaction conditions on isomerization wasdiscussed, and mechanism of the catalytic isomerization was confirmed by thestructural identification of two byproducts.2. The design, synthesis and activity of harmine derivatives wereinvestigated. 1-Amino-7-methoxy-β-carboline was obtained using6-bromo-indole as starting material by 11 steps via the nucleophilicsubstitution, Vilsmeier-Haack, Knoevenagel condensation, reduction andPictet-Spengler as key steps. Nine 1-alkoxy carbonylamino-7-methoxy-β-carbolines were synthesized from intermediate carbonyl azide with thecorresponding alcohols via the Curtius rearrangement.The antitumor activity of the above ten new compounds on MCF-7cell was tested. The results showed that theβ-carboline derivatives haveanticancer activity, and further research work is in progress.
Keywords/Search Tags:α-Asarone, Wittig reaction, palladium(II) catalyst, carbocation mechanism, anti-tumor activity, harmine derivatives, synthesis
PDF Full Text Request
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