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. 2010 Jul 2;12(13):2982-5.
doi: 10.1021/ol1010032.

Electrophilic aromatic selenylation: new OPRT inhibitors

Mohannad Abdo  1 , Yong Zhang, Vern L Schramm, Spencer Knapp
Affiliations

Electrophilic aromatic selenylation: new OPRT inhibitors

Mohannad Abdo et al. Org Lett. .

Abstract

2-Ethoxyethaneseleninic acid reacts with electron-rich aromatic substrates to deliver, by way of the selenoxides, the (2-ethoxyethyl)seleno ethers, which can in turn be transformed into a diverse set of aryl-selenylated products. Among these, a family of 5-uridinyl derivatives shows submicromolar inhibition of human and malarial orotate phosphoribosyltransferase.

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Figures

Scheme 1
Scheme 1
Electrophilic Selenylation with EtOCH2CH2SeO2H
Scheme 2
Scheme 2
Selenylation in Aqueous Solution
Scheme 3
Scheme 3
Selenylation of tyrosine and tryptophan derivatives
Scheme 4
Scheme 4
Oxidation of 5-Selenylated Nucleosides
Scheme 5
Scheme 5
Oxidation of Selenylated Tyrosine Derivative
Scheme 6
Scheme 6
Full Product Analysis of Selenylation Reactions
Scheme 7
Scheme 7
Control Reactions for Selenylation Mechanism
Scheme 8
Scheme 8
Transformations of ArSeOH
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