Synthesis and Biological Profiling of Benzofuro-Fused 7-Deazapurine Nucleosides

0577107 - ÚOCHB 2024 RIV DE eng J - Journal Article
Yang, Chao - Tichý, Michal - Poštová Slavětínská, Lenka - Vaiedelich, Enzo - Gurská, S. - Džubák, P. - Hajdúch, M. - Hocek, Michal
Synthesis and Biological Profiling of Benzofuro-Fused 7-Deazapurine Nucleosides.
European Journal of Organic Chemistry. Roč. 26, č. 44 (2023), č. článku e202300723. ISSN 1434-193X. E-ISSN 1099-0690
R&D Projects: GA MŠMT LX22NPO5102
Research Infrastructure: CZ-OPENSCREEN IV - 90252; EATRIS-CZ IV - 90253
Institutional support: RVO:61388963
Keywords : cross-coupling * cytotoxicity * glycosylation * nucleosides * 7-deazapurine
OECD category: Organic chemistry
Impact factor: 2.8, year: 2022
Method of publishing: Open access
https://doi.org/10.1002/ejoc.202300723

A series of benzofuro-fused 7-deazapurine (6H-furo[2,3-e]pyrimido[4,5-b]indole) 2’-deoxyribo- and ribonucleosides was designed and synthesized. The synthesis of key compound 10-chloro-6H-furo[2,3-e]pyrimido[4,5-b]indole was based on the Negishi cross-coupling of iodobenzofurane with zincated 4,6-dichloropyrimidine followed by azidation and photochemical cyclization. Glycosylation of the heterocycle with either Hoffer's chlorodeoxyribose or protected ribose followed by cross-coupling or substitution reactions at position 10 gave the desired two sets of final nucleosides that showed moderate to weak cytostatic activity and interesting fluorescence properties.
Permanent Link: https://hdl.handle.net/11104/0346357