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Studies on the Synthesis of Bioactive Benzofuran Neolignans and Mannich Alkali Derivatives

Author: LiuShuangYan
Tutor: WangQiuAn
School: Hunan University
Course: Organic Chemistry
Keywords: Benzofurans Benzodioxanes Neolignans Mannich alkali Synthesis Biological activity
CLC: O629
Type: Master's thesis
Year: 2013
Downloads: 29
Quote: 0
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Abstract


Benzofuran and benzodioxane neolignans are a kind of natural organic productswith important significance for the development of drugs. They have excellentbioactivity, such as antioxidation, antineoplastic, antiviral, antiphlogosis andsterilization. Mannich alkaloid is a kind of organic nitrogen compounds in the nature,and an effective component in Chinese herbs, they possess significant physiologicalactivity, such as antineoplastic, antiphlogosis, sterilization, hypotensive andabirritation. So we hope to get more bioactive compounds through the chemosynthesisand structure modification of benzofuran and benzodioxane neolignans.This thesis studied the total synthesis of benzofuran and benzoxioxaneneolignans with their Mannich alkali derivatives.1、Compound2-(3’,4’-dihydroxyphenyl)-3-methoxy carbonyl-5-methoxycarbonyl vinyl-7-hydroxy-2,3-dihydrobenzofuran (1) and compound2-(3’,4’-dihydroxyphenyl)-3-methoxy carbonyl-6-methoxy carbonyl vinyl-2,3-dihydro-1,4-benzodioxane (2) were synthesized from caffeic acid through esterification andbiomimetic oxidative coupling reaction. Then a series of benzofuran andbenzodioxane neolignans4~7、8~16were synthesized through acetylation, DDQoxydehydrogenation, Pd/C catalytic hydrogenation, lithium aluminium hydridereduction and deacetylation in alkaline condition.2、The natural dihydrobenzofuran neolignans licarin A (17) was synthesized fromisoeugenol through biomimetic oxidative coupling. Then under acid condition andsystem of ethanol or methanol, seven new licarin A Mannich alkali derivatives18~24were synthesized in Mannich reaction using licarin A, formaldehyde and secondaryamine as the material.3、The synthesized compounds were evaluated for biological activity against fivehuman cancer cell lines by the standard MTT method. According to the bioactiveresearch, compound1、8、9have an inhibitory effect on leukemia cells (HL-60), lungcarcinoma cell (A-549), breast cancer cell (MCF-7), colon cancer cell (SW-480),hepatoma carcinoma cell (SMMC-7721); Compound10has an inhibitory effect onleukemia cells (HL-60), lung carcinoma cell (A-549), breast cancer cell (MCF-7),hepatoma carcinoma cell (SMMC-7721).4、Twenty-three neolignans compounds were synthesized in total in this thesis. They were benzofuran neolignans, benzodioxane neolignans and dihydrobenzofuranMannich alkali derivatives. Among them, sixteen were new compounds. Theirstructures were confirmed by1H NMR,13C NMR and MS spectra.

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