Note: / Recent years have witnessed a tremendous growth in the number of goldcatalyzeddevelop new gold catalytic methods to mediate carbon-carbon, carbon-oxygenand carbon-nitrogen bond forming reactions. Chapter 2 describes new annulations catalyzed by gold(I) of simple 0-hydroxyaldehydes with alkynes. This annulation efficiently generates isoflavanone-type structures, which have many possible applications in the synthesis of isoflavanone natural products. This chapter details the development and the optimization of the reaction conditions. The annulation was applied to various aldehydes and arylalkynes with good efficiency. Furthermore, it incorporated all atoms of both starting materials into the product and thus has a theoretical atom economy of 100%. Chapter 3 extends the scope of the annulations developed in Chapter 2. Indeed, 2,3-dihydro-l-tosylquinolin-3(1H)-one derivatives, aza-isoflavanones, have been efficiently synthesized via a gold-catalyzed annulation of 2-tosylaminobenzaldehyde and alkynes. The annulation was applied to various arylalkynes with good efficiency. This annulation can be used for the synthesis of a range of potentially bioactive molecules. [...] / Récemment nous avons constate une énorme croissance de l'utilisation de l'or comme nouveau catalyseur dans de nombreuses transformations chimiques sélectives. Le but de cette étude était de développer de nouvelles méthodes catalytiques en utilisant I' or pour former de nouveaux liens carbone-carbone, carbone-oxygène et carbone-azote. Dans le chapitre 2, nous décrirons la nouvelle addition catalysée par Por(I) entre des 2-hydroxyaldehydes et des alcynes. Cette addition produit des structures de type isoflavanones efficacement. Ces derniers sont impliques dans la synthèse de nombreux produits nature Is. L' addition a été appliquée efficacement diversaldéhydes et alcynes. En outre, l'addition a incorpore tous les atomes des produits de départ au produit final et a ainsi une économie d'atome théorique de 100%. Le développement et l'optimisation des conditions de réaction seront détailles dans ce chapitre.[...]

Recent years have witnessed a tremendous growth in the number of gold-catalyzed highly selective chemical transformations. The aim of this study was to develop new gold catalytic methods to mediate carbon-carbon, carbon-oxygen and carbon-nitrogen bond forming reactions. / Chapter 2 describes new annulations catalyzed by gold(I) of simple o-hydroxyaldehydes with alkynes. This annulation efficiently generates isoflavanone-type structures, which have many possible applications in the synthesis of isoflavanone natural products. This chapter details the development and the optimization of the reaction conditions. The annulation was applied to various aldehydes and arylalkynes with good efficiency. Furthermore, it incorporated all atoms of both starting materials into the product and thus has a theoretical atom economy of 100%. / Chapter 3 extends the scope of the annulations developed in Chapter 2. Indeed, 2,3-dihydro-1-tosylquinolin-3(1H)-one derivatives, aza-isoflavanones, have been efficiently synthesized via a gold-catalyzed annulation of 2-tosylaminobenzaldehyde and alkynes. The annulation was applied to various arylalkynes with good efficiency. This annulation can be used for the synthesis of a range of potentially bioactive molecules. / Chapter 4 describes applications in the total synthesis of the annulation developed in chapter 2. (+/-)-Pterocarpan and analogues have been efficiently synthesized via the annulation of salicylaldehydes and o-methoxymethoxylphenylacetylene followed by a one-pot reduction and acidic cyclization of the ketones. In addition, isoflavone derivatives have been synthesized rapidly via the annulation of salicylaldehyde and arylacetylenes followed by IBX/DMSO oxidation of the isoflavanones. / As part of our ongoing studies on metal-catalyzed atom economical reactions, the gold/silver-catalyzed addition of arenes to mono-substituted allene, generate exclusive terminal addition products are described in Chapter 5. / Finally, Appendix A explores the use of commercially available polymer-supported triphenylphosphine as a catalyst for the efficient gamma-addition of methyl 2-butynoate with various pronucleophiles. In addition, optimization studies shows no need of a co-catalyst for the reaction in the presence of a mixture of water:toluene (5:1). The polymer-supported triphenylphosphine is recoverable and can be reused efficiently. This gamma-addition is highly atom-economical and the reaction time was reduced under microwave irradiation.

No description available.

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Yuen, Ka Leung. / Thesis (M.Phil.)--Chinese University of Hong Kong, 2009. / Includes bibliographical references (leaves 95-104). / Abstracts in English and Chinese. / Chapter 1 --- Introduction / Chapter 1.1 --- CANCER / Chapter 1.1.1 --- OVERVIEW OF CANCER --- p.1 / Chapter 1.1.2 --- DEVELOPMENT OF CANCER --- p.1 / Chapter 1.1.3 --- CHARACTERISTICS OF CANCER CELLS --- p.3 / Chapter 1.1.4 --- CATEGORIZATION OF CANCER --- p.6 / Chapter 1.1.5 --- RISK FACTORS IN CANCER DEVELOPMENT --- p.7 / Chapter 1.1.6 --- EPIDEMIOLOGY OF CANCER --- p.11 / Chapter 1.1.7 --- CANCER THERAPIES --- p.13 / Chapter 1.2 --- SOYBEANS AND ISOFLAVONES / Chapter 1.2.1 --- GENERAL INTRODUCTION OF ISOFLAVONES --- p.18 / Chapter 1.2.2 --- NATURAL FUNCTIONS OF ISOFLAVONES --- p.19 / Chapter 1.2.3 --- STRUCTURES OF ISOFLAVONES --- p.19 / Chapter 1.2.4 --- BIOACTIVITIES OF SOY ISOFLAVONES --- p.20 / Chapter 1.2.5 --- PRODUCTION OF SOY ISOFLAVONES CAN BE AFFECTED BY MANY FACTORS --- p.21 / Chapter 1.3 --- THE AIM AND OBJECTIVES OF THE PROJECT / Chapter 1.3.1 --- AIM OF THE PROJECT --- p.22 / Chapter 1.3.2 --- OBJECTIVES OF THE PROJECT --- p.23 / Chapter 2 --- Materials / Chapter 2.1 --- 19 DROUGHT TOLERANT SOYBEAN LINES --- p.24 / Chapter 2.2 --- 5 HUMAN CANCER CELL LINES --- p.25 / Chapter 2.3 --- CHEMICALS --- p.25 / Chapter 2.4 --- REAGENTS --- p.26 / Chapter 2.5 --- SOLUTIONS --- p.26 / Chapter 2.6 --- MAJOR EQUIPMENTS AND MATERIALS --- p.28 / Chapter 3 --- Methodology / Chapter 3.1 --- PREPARATION OF SOYBEAN EXTRACTS --- p.29 / Chapter 3.2 --- HIGH PERFORMANCE LIQUID CHROMATOGRAPHY(HPLC) ANALYSIS OF SOYBEAN EXTRACTS / Chapter 3.2.1 --- PREPARATION OF SOYBEAN EXTRACTS FOR HPLC ANALYS --- p.30 / Chapter 3.2.2 --- HPLC ANALYSIS --- p.30 / Chapter 3.3 --- PREPARATION OF 5 HUMAN CANCER CELL LINES FOR ANTI-PROLIFERATION ASSAY / Chapter 3.3.1 --- THAWING OF THE C Y R O P R E S E R V E D CELL LINES --- p.31 / Chapter 3.3.2 --- MAINTAINING OF CELL LINES --- p.32 / Chapter 3.3.3 --- ANTI-PROLIFERATION TEST WITH MTT ASSAY --- p.33 / Chapter 3.4 --- STATISTICS --- p.35 / Chapter 4 --- Results / Chapter 4.1 --- PREPARARTION OF SOYBEAN EXTRACTS --- p.36 / Chapter 4.2 --- HPLC ANALYSIS OF 5 SELECTED ISOFLAVONES IN 19 SOYBEAN SAMPLES --- p.36 / Chapter 4.3 --- COMPARISON OF SUM OF 5 SELECTED ISOFLAVONES FROM THE PARENT SOYBEAN AND VARIETIES HARVESTED FROM IRRIGATED LAND --- p.43 / Chapter 4.4 --- COMPARISON OF SUM OF 5 SELECTED ISOFLAVONES FROM THE SOYBEAN VARIETIES HARVESTED FROM DROUGHT LAND --- p.45 / Chapter 4.5 --- COMPARISON OF SELECTED ISOFLAVONES FROM THE PARENT SOYBEAN AND VARIETIES HARVESTED FROM IRRIGATED LAND --- p.47 / Chapter 4.6 --- COMPARISON OF SELECTED ISOFLAVONES FROM THE PARENT SOYBEAN AND VARIETIES HARVESTED FROM DAROUGHT LAND --- p.54 / Chapter 4.7 --- COMPARISON OF SUM OF SELECTED ISOFLAVONES AMONG THE SOYBEANS HARVESTED FROM IRRIGATED LAND AND DROUGHT LAND --- p.59 / Chapter 4.8 --- DETERMINATION OF ANTI-PROLIFERATION ABILITIES OF SOYBEAN SAMPLES --- p.19 / Chapter 4.8.1 --- ANTI-PROLIFERATION TEST OF ETHANOL AND 2-PHEN YLCHROMONE --- p.61 / Chapter 4.8.2 --- ANTI-PROLIFERATION ACTIVITIES OF 19 SOYBEAN SAMPLES ON 5 HUMAN CANCER CELL LINES --- p.61 / Chapter 4.9 --- COMPARISON OF ANTI-PROLIFERATION POTENCIES OF19 SOYBEAN SAMPLES WITH SUM OF SELECTED ISOFLAVONES --- p.70 / Chapter 4.10 --- COMPARISON OF ANTI-PROLIFERATION POTENCIES OF19 SOYBEAN SAMPLES --- p.72 / Chapter 4.11 --- ANTI-PROLIFERATION EFFECT OF INDIVIDUAL ISOFLAVONES ON FIVE CANCER CELL LINES --- p.74 / Chapter 5 --- Discussion / Chapter 5.1 --- EXTRACTION OF 19 SOYBEAN LINES --- p.77 / Chapter 5.2 --- DETERMINATION OF QUANTITIES OF SELECTED ISOFLAVONES IN 19 SOYBEAN SAMPLES BY HPLC ANALYSIS --- p.77 / Chapter 5.3 --- COMPARISON OF SELECTED ISOFLAVONES AMONG 19 SOYBEAN SAMPLES / Chapter 5.3.1 --- COMPARISON OF SUM OF SELECTED ISOFLAVONES BETWEEN PARENT AND SOYBEANS HARVESTED FROM IRRIGATED LAND --- p.80 / Chapter 5.3.2 --- COMPARISON OF SUM OF SELECTED ISOFLAVONES BETWEEN SOYBEANS HARVESTED FROM DROUGHT LAND --- p.81 / Chapter 5.3.3 --- COMPARISON OF SELECTED ISOFLAVONES BETWEEN SOYBEANS HARVESTED FROM IRRIGATED LAND --- p.81 / Chapter 5.3.4 --- COMPARISON OF SELECTED ISOFLAVONES BETWEEN SOYBEANS HARVESTED FROM DROUGHT LAND --- p.82 / Chapter 5.3.5 --- COMPARISON OF SUM OF SELECTED ISOFLAVONES BETWEEN SOYBEANS HARVESTED FROM IRRIGATED LAND AND DROUGHT LAND --- p.83 / Chapter 5.4 --- COMPARISON OF ANTI-PROLIFERATION ACTIVITIES OF 19 SOYBEAN SAMPLES / Chapter 5.4.1 --- COMPARISON OF ANTI-PROLIFERATION ACTIVITIES OF19 SOYBEAN SAMPLES AMONG 5 CANCER CELL LINES --- p.84 / Chapter 5.4.2 --- COMPARISON OF ANTI-PROLIFERATION POTENCIES OF19 SOYBEAN SAMPLES --- p.85 / Chapter 5.4.3 --- COMPARISON OF ANTI-PROLIFERATION ACTIVITIES OF19 SOYBEAN SAMPLES AND CORRESPONDING SUM OF SELECTED ISOFLAVONES --- p.86 / Chapter 5.4.4 --- COMPARISON OF IC50S FROM SOYBEANS HARVESTED FROM IRRIGATED LAND AND DROUGHT LAND --- p.87 / Chapter 5.4.5 --- CORRELATION OF ISOFLAVONES AND ANTI-PROLIFERATION POTENCIES --- p.88 / Chapter 6 --- Conclusion --- p.90 / Chapter 7 --- References --- p.91 / Chapter 8 --- Appendix --- p.S1