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

Yang, Chao; Tichý, Michal; Poštová Slavětínská, Lenka; Vaiedelich, Enzo; Gurská, S.; Džubák, P.; Hajdúch, M.; Hocek, Michal

doi:https://dx.doi.org/10.1002/ejoc.202300723

Number of the records: 1

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

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SYSNO ASEP	0577107
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Synthesis and Biological Profiling of Benzofuro-Fused 7-Deazapurine Nucleosides
Author(s)	Yang, Chao (UOCHB-X)_ORCID Tichý, Michal (UOCHB-X)_{RID, ORCID} Poštová Slavětínská, Lenka (UOCHB-X)_RID Vaiedelich, Enzo (UOCHB-X)_ORCID Gurská, S. (CZ) Džubák, P. (CZ) Hajdúch, M. (CZ) Hocek, Michal (UOCHB-X)_{RID, ORCID}
Article number	e202300723
Source Title	European Journal of Organic Chemistry - ISSN 1434-193X Roč. 26, č. 44 (2023)
Number of pages	6 s.
Language	eng - English
Country	DE - Germany
Keywords	cross-coupling ; cytotoxicity ; glycosylation ; nucleosides ; 7-deazapurine
OECD category	Organic chemistry
R&D Projects	LX22NPO5102 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
Research Infrastructure	CZ-OPENSCREEN IV - 90252 - Ústav molekulární genetiky AV ČR, v. v. i. EATRIS-CZ IV - 90253 - Univerzita Palackého v Olomouci / Lékařská fakulta
Method of publishing	Open access
Institutional support	UOCHB-X - RVO:61388963
UT WOS	001090866900001
EID SCOPUS	85174603349
DOI	10.1002/ejoc.202300723
Annotation	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.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
Year of Publishing	2024
Electronic address	https://doi.org/10.1002/ejoc.202300723

Number of the records: 1