Synthesis 2017; 49(20): 4623-4650
DOI: 10.1055/s-0036-1588443
special topic
© Georg Thieme Verlag Stuttgart · New York

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

Nazarii Sabat
a  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
b  Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 12843 Prague 2, Czech Republic   Email: hocek@uochb.cas.cz
,
Sabina Smoleń
a  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
,
Petr Nauš
a  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
,
Pavla Perlíková
a  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
,
Magdaléna Cebová
a  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
,
Lenka Poštová Slavětínská
a  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
,
Michal Hocek*
a  Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nam. 2, 16610 Prague 6, Czech Republic
b  Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 12843 Prague 2, Czech Republic   Email: hocek@uochb.cas.cz
› Author Affiliations
This work was supported by the Academy of Sciences of the Czech Republic (RVO 61388963 and the Praemium Academiae award to M. Hocek), by the Czech Science Foundation (16-0011785 to N. S. and M. H.), by the Czech Health Research Council (15-31984A to S. S.), and by Gilead Sciences, Inc.
Further Information

Publication History

Received: 29 March 2017

Accepted after revision: 02 May 2017

Publication Date:
20 June 2017 (online)

Published as part of the Special Topic Modern Strategies for Heterocycles Synthesis

Abstract

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.

Supporting Information

 
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