The syntheses and properties of tricyclic pyrrolo[2,3-d]pyrimidine analogues of S6-methylthioguanine and O6-methylguanine

Organic & Biomolecular Chemistry
Ana R Hornillo-AraujoDavid M Williams

Abstract

The syntheses of novel tricyclic pyrrolo[2,3-d]pyrimidine analogues of S6-methylthioguanine are described. The crystal structures and pKa values of these and related O6-methylguanine analogues are reported. All compounds display higher pKa values than O6-methylguanine with the sulfur-containing analogues being the more basic and exhibiting higher stability in aqueous solution. In a standard substrate assay with the human repair protein O6-methylguanine-DNA methyltransferase (MGMT) only the oxygen-containing analogue displayed activity.

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Citations

Dec 7, 2007·Nucleosides, Nucleotides & Nucleic Acids·Ana R Hornillo-AraujoDavid M Williams
Dec 25, 2015·Chemical Reviews·Laurens M De CoenChristian V Stevens
Apr 23, 2009·Chemical Reviews·K C Kumara SwamyK V P Pavan Kumar

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