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Synthesis of Polycyclic Hetero-Fused 7-Deazapurine Heterocycles and Nucleosides through C-H Dibenzothiophenation and Negishi Coupling
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SYSNO ASEP 0563594 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Synthesis of Polycyclic Hetero-Fused 7-Deazapurine Heterocycles and Nucleosides through C-H Dibenzothiophenation and Negishi Coupling Tvůrce(i) Yang, Chao (UOCHB-X) ORCID
Poštová Slavětínská, Lenka (UOCHB-X) RID
Fleuti, Marianne (UOCHB-X) ORCID
Klepetářová, Blanka (UOCHB-X) RID, ORCID
Tichý, Michal (UOCHB-X) RID, ORCID
Gurská, S. (CZ)
Pavliš, P. (CZ)
Džubák, P. (CZ)
Hajdúch, M. (CZ)
Hocek, Michal (UOCHB-X) RID, ORCIDZdroj.dok. Journal of the American Chemical Society. - : American Chemical Society - ISSN 0002-7863
Roč. 144, č. 42 (2022), s. 19437-19446Poč.str. 10 s. Jazyk dok. eng - angličtina Země vyd. US - Spojené státy americké Klíč. slova enzymatic incorporation ; antiviral activity ; analogs Obor OECD Biochemistry and molecular biology CEP LX22NPO5102 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy LM2018133 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Výzkumná infrastruktura CZ-OPENSCREEN III - 90130 - Ústav molekulární genetiky AV ČR, v. v. i. Způsob publikování Open access Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000873799700001 EID SCOPUS 85140486506 DOI 10.1021/jacs.2c07517 Anotace A new approach for synthesizing polycyclic heterofused 7-deazapurine heterocycles and the corresponding nucleosides was developed based on C-H functionalization of diverse (hetero)aromatics with dibenzothiophene-S-oxide followed by the Negishi cross-cooupling with bis(4,6-dichloropyrimidin-5-yl)zinc. This cross-coupling afforded a series of (het)aryl-pyrimidines that were converted to fused deazapurine heterocycles through azidation and thermal cyclization. The fused heterocycles were glycosylated to the corresponding 2′-deoxy- and ribonucleosides, and a series of derivatives were prepared by nucleophilic substitutions at position 4. Four series of new polycyclic thieno-fused 7-deazapurine nucleosides were synthesized using this strategy. Most of the deoxyribonucleosides showed good cytotoxic activity, especially for the CCRF-CEM cell line. Phenyl- and thienyl-substituted thieno-fused 7-deazapurine nucleosides were fluorescent, and the former one was converted to 2′-deoxyribonucleoside triphosphate for enzymatic synthesis of labeled oligonucleotides. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Rok sběru 2023 Elektronická adresa https://doi.org/10.1021/jacs.2c07517
Počet záznamů: 1