Dissertation > Medicine, health > Pharmacy > Drug basic science > Medicinal Chemistry

Gold-catalyzed Addition Reaction of Sulfonates and Alkynes and Study of Synthesis and Bioactivity of (E)-3-phenyl-substituted Acrylic Acids

Author QiJianFeng
Tutor ZhangChen
School Zhejiang University
Course Medicinal Chemistry
Keywords Gold catalytic Vinyl sulfonates Derivatives of salvlanol acid F Synthesis Activity
CLC R914
Type Master's thesis
Year 2011
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Vinyl sulfonates are important chemical intermediates, which widely used in pesticides, pharmaceuticals and other synthetic fields. Synthesis of vinyl sulfonates compounds had few reports so far, and mainly synthesised through the enolization of the ketone and then reacted with sulfonic anhydride. The reaction generally required at very low temperature. We had developed a method catalyzed by gold complexes through sulfonic acid and alkynes into the vinyl sulfonates [China Patent:Public No. CN1013140A; Chem. Commun,2009,1577-1579], the yield of the corresponding vinyl sulfonates is in the range of 30%to 90%. But the sulfonic acid has strong corrosive, it will lead to higher equipment requirement in industrial, so therefore its application in production is limited. The first part of this dissertation describes the improvement of the method. On its basis, instead, we use acid salt, replaced the strong corrosive acid, greately enhanced the value of the reaction.Another part of this article is the study of synthesis and biological activity of trans-3-substituted phenyl acrylic acid. Trans-3-(2-(3,4-Dihydroxy vinyl)-3,4-dihydroxyphenyl) acrylate (Sal F). Sal F is an important fragment of Sal A. Recent studies show the significant activity of Sal A in the cardiovascular system protection, anti-liver damage and anti-tumor. And its most prominent feature is the extraordinary effects of scavenging free radical and antioxidant. With the continuous development of medical technology, the new use of Sal A will be further excavated, and its mechanism will be further clarified. Sal F, as a part of Sal A, has a good pharmacological activity in cardiovascular system protection. Our group do a deep analysis of Sal F after a comprehensive literature survey, specific to the structure characteristics of Sal F. We synthesis of 9 new derivatives of Sal F after the improvement of traditional synthetic methods which confirmed by 1H-NMR、13C-NMR、MS. We focused on the pharmacological activity of tetramethyl Sal F. Function of anti-vascular endothelial cell injury are measured in vitro model of anoxia and low lever of glucose, as well as a tolerance estimation under normal air pressure with hypoxia by nitrite-poisoned mice survival time model, compounds’protection for injured mice’s brain by model filling after Cerebral artery occlusion. Activity were measured by the above ways, The results showed that:some of the compounds showed a good protective effect of cardiovascular system and are almost non-cytotoxic, that can be used as a treatment of cardiovascular damage.

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