Stereo-defined synthesis of 5'-(Z)-substituted 4',5'-unsaturated adenosines and evaluation of their inhibitory activity against S-adenosyl homocysteine hydrolase.

Hiroki Kumamoto, Sayoko Onuma, Hiromichi Tanaka, Yukio Kitade
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引用次数: 1

Abstract

A new approach was developed for the synthesis of 5'-(Z)-substituted 4',5'-unsaturated adenosines, potential inhibitors against S-adenosyl-L-homocysteine hydrolase (SAHase). A highly stereoselective radical-mediated sulfur-extrusive stannylation was employed as a key step in the present approach. Inhibitory activity of the compounds against SAHase is also presented.

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立体定向合成5′-(Z)-取代4′,5′-不饱和腺苷及其对s -腺苷同型半胱氨酸水解酶抑制活性的评价
研究了5′-(Z)-取代的4′,5′-不饱和腺苷的合成方法,这是s -腺苷- l-同型半胱氨酸水解酶(SAHase)的潜在抑制剂。高度立体选择性自由基介导的硫挤压锡化反应是本方法的关键步骤。化合物对SAHase的抑制活性也得到了证实。
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Analogues of cyclic adenosine 5'-diphosphate ribose and adenophostin A, nucleotides in cellular signal transduction. Molecular recognition in P2 nucleotide receptors. Synthesis of carbocyclic and acyclic nucleosides possessing 2-fluoroadenine derivatives and their inhibitory activities against Plasmodium falciparum SAH hydrolase. Stereoselective synthesis of 2'-beta-carbon-substituted 2'-deoxy-4'-thioribonucleosides from 4-thiofuranoid glycal. Synthetic studies and properties of N-tert-butylaminoxyl nucleosides.
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