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

0480257 - ÚOCHB 2018 RIV DE eng J - Journal Article
Sabat, Nazarii - Smolen, Sabina - Nauš, Petr - Perlíková, Pavla - Cebová, M. - Poštová Slavětínská, Lenka - Hocek, Michal
Synthesis of 2,6-Substituted 7-(Het)aryl-7-deazapurine Nucleobases (2,4-Disubstituted 5-(Het)aryl-pyrrolo[2,3-d]pyrimidines).
Synthesis. Roč. 49, č. 20 (2017), s. 4623-4650. ISSN 0039-7881. E-ISSN 1437-210X
R&D Projects: GA ČR(CZ) GA16-00178S; GA MZd(CZ) NV15-31984A
Grant - others:AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963
Keywords : deazapurines * pyrrolo[2,3-d]pyrimidines * nucleobases * Suzuki-Miyaura cross-coupling * deprotection * demethylation
OECD category: Organic chemistry
Impact factor: 2.722, year: 2017

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.
Permanent Link: http://hdl.handle.net/11104/0276103