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Synthesis of 2-substituted 9-oxa-guanines {5-aminooxazolo[5,4-<i>d</i>]pyrimidin-7(6<i>H</i>)-ones} and 9-oxa-2-thio-xanthines {5-mercaptooxazolo[5,4-<i>d</i>]pyrimidin-7(6<i>H</i>)-ones}

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Abstract

Oxazolo[5,4-<i>d</i>]pyrimidines can be considered as 9-oxa-purine analogs of naturally occurring nucleic acid bases. Interest in this ring system has increased due to recent reports of biologically active derivatives. In particular, 5-aminooxazolo[5,4-<i>d</i>]pyrimidine-7(6<i>H</i>)-ones (9-oxa-guanines) have been shown to inhibit ricin. The preparation of a series of 2-substituted 5-aminooxazolo[5,4-<i>d</i>]pyrimidin-7(6<i>H</i>)-ones and related 5-thio-oxazolo[5,4-<i>d</i>]pyrimidines is described, including analogs suitable for further elaboration employing &#8220;click&#8221; chemistry utilizing copper-catalyzed Huisgen 1,3-dipolar cycloadditions. Two of the compounds prepared were found to inhibit ricin with IC<sub>50</sub> <i>ca.</i> 1&#8211;3 mM

Topics: Annulation, Click Chemistry, Cyclization, Purine Analogs, Ricin, Organic chemistry, QD241-441, Chemistry, QD1-999, Science, Q, DOAJ:Organic Chemistry, DOAJ:Chemistry
Publisher: Beilstein-Institut
Year: 2008
DOI identifier: 10.3762/bjoc.4.26
OAI identifier: oai:doaj.org/article:086eb1ff45314d85a7c8562e522b331b
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