Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6‐(Thiophen‐2‐yl)‐7‐fluoro‐7‐deazapurine

0509096 - ÚOCHB 2020 RIV DE eng J - Journal Article
Malnuit, Vincent - Smolen, Sabina - Tichý, Michal - Poštová Slavětínská, Lenka - Hocek, Michal
Synthesis of Cyclic and Acyclic Nucleoside Phosphonates and Sulfonamides Derived from 6‐(Thiophen‐2‐yl)‐7‐fluoro‐7‐deazapurine.
European Journal of Organic Chemistry. Roč. 2019, 31/32 (2019), s. 5409-5423. ISSN 1434-193X. E-ISSN 1099-0690
R&D Projects: GA ČR(CZ) GA19-08124S; GA MZd(CZ) NV15-31984A
Grant - others:AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963
Keywords : 7‐deazapurine * nucleoside phosphonates * structure‐activity relationships * synthetic methods * sulfonamides
OECD category: Organic chemistry
Impact factor: 2.889, year: 2019
Method of publishing: Limited access
https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201900509

Ribonuclosides derived from 6-hetaryl-7-dezapurines are potent cytostatics, but their mechanism of action is unknown. Here we designed and synthesized a series of cyclic and acyclic nucleoside phosphonates, as well as carboxy, cyano, sulfo, and sulfonamide acyclic analogues derived from 6-thiophen-2-yl-7-deazapurine and 7-fluoro-6-thiophen-2-yl-7-deazapurine as ribonucleoside monophosphate mimics. None of these analogues exerted significant cytotoxic and antiviral activity.
Permanent Link: http://hdl.handle.net/11104/0299888