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乙烯砜:合成制备及药物化学应用

Vinyl sulfones: synthetic preparations and medicinal chemistry applications.

作者信息

Meadows D Christopher, Gervay-Hague Jacquelyn

机构信息

Department of Chemistry, University of California, Davis, California 95616, USA.

出版信息

Med Res Rev. 2006 Nov;26(6):793-814. doi: 10.1002/med.20074.

DOI:10.1002/med.20074
PMID:16788979
Abstract

Vinyl sulfones have long been known for their synthetic utility in organic chemistry, easily participating in 1,4-addition reactions and cycloaddition reactions. This functional group has also recently been shown to potently inhibit a variety of enzymatic processes providing unique properties for drug design and medicinal chemistry. This review includes traditional methods used for the synthesis of vinyl sulfones, but focuses mainly on newer reactions applied to vinyl sulfones, including olefin metathesis, conjugate reduction, asymmetric dihydroxylation (AD), and the use of vinyl sulfones to arrive at highly functionalized targets, all illustrating the rich and versatile chemistry this group can efficiently perform. In addition, geminal disulfones are discussed with respect to their formation, reactions, and medicinal applications of this underutilized functional group.

摘要

长期以来,人们一直都知道乙烯基砜在有机化学合成中的用途,它很容易参与1,4 - 加成反应和环加成反应。最近还发现这个官能团能有效抑制多种酶促过程,为药物设计和药物化学提供了独特的性质。这篇综述包括了用于合成乙烯基砜的传统方法,但主要聚焦于应用于乙烯基砜的新反应,包括烯烃复分解反应、共轭还原反应、不对称双羟基化反应(AD),以及利用乙烯基砜得到高度官能化的目标产物,所有这些都说明了该官能团能够高效进行丰富多样的化学反应。此外,还讨论了偕二砜的形成、反应及其在药物方面的应用,这是一个未得到充分利用的官能团。

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Vinyl sulfones: synthetic preparations and medicinal chemistry applications.乙烯砜:合成制备及药物化学应用
Med Res Rev. 2006 Nov;26(6):793-814. doi: 10.1002/med.20074.
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Catalytic asymmetric synthesis of γ-substituted vinyl sulfones.γ-取代乙烯基砜的催化不对称合成。
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Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones.使用乙烯基砜进行催化对映选择性碳-碳键形成共轭加成反应。
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J Org Chem. 2007 Dec 21;72(26):9924-35. doi: 10.1021/jo7016197. Epub 2007 Nov 30.

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