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Synthesis of 2,6-Substituted 7-(Het)aryl-7-deazapurine Nucleobases (2,4-Disubstituted 5-(Het)aryl-pyrrolo[2,3-d]pyrimidines)

DOI: 10.1055/s-0036-1588443

A series of 7-(het)aryl-7-deazapurine nucleobases (5-[(het)aryl]-2,4-disubstituted 7H-pyrrolo[2,3-d]pyrimidines) bearing NH2, OMe, SMe, or Me groups at position 6 and H, NH2, or Me at position 2 were prepared by the aqueous Suzuki–Miyaura cross-coupling reactions from SEM-protected 7-iodo-7-deazapurines with (het)arylboronic acids followed by deprotection. The 6-methoxy derivatives were further transformed into 7-deazahypoxanthines or 7-deazaguanines by O-demethylation reactions. Unlike their ribonucleoside counterparts, the 7-deazapurine nucleobases did not exert any significant cytostatic or antiviral effects.

© Georg Thieme Verlag Stuttgart · New York

Artikel in Thieme eJournals:
Inhaltsverzeichnis  |  Abstract  |  Volltext

Authors:   Nazarii Sabat; Sabina Smoleń; Petr Nauš; Pavla Perlíková; Magdaléna Cebová; Lenka Poštová Slavětínská; Michal Hocek
Journal:   Synthesis
Volume:   44
edition:   eFirst
Year:   2017
Pages:   1247
DOI:   10.1055/s-0036-1588443
Publication date:   20-Jun-2017
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