BIOMAT Database Logo BIOMAT Database Logo

Synthesis and Biological Profiling of Quinolino-Fused 7-Deazapurine Nucleosides. 2024

Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, Prague 2 CZ-12843, Czech Republic.

A series of quinolino-fused 7-deazapurine (pyrimido[5',4':4,5]pyrrolo[3,2-f]quinoline) ribonucleosides were designed and synthesized. The synthesis of the key 11-chloro-pyrimido[5',4':4,5]pyrrolo[3,2-f]quinoline was based on the Negishi cross-coupling of iodoquinoline with zincated 4,6-dichloropyrimidine followed by azidation and thermal or photochemical cyclization. Vorbrüggen glycosylation of the tetracyclic heterocycle followed by cross-coupling or substitution reactions at position 11 gave the desired set of final nucleosides that showed moderate to weak cytostatic activity and fluorescent properties. The corresponding fused adenosine derivative was converted to the triphosphate and successfully incorporated to RNA using in vitro transcription with T7 RNA polymerase.

UI MeSH Term Description Entries

Related Publications

Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis and Biological Profiling of Pyrazolo-Fused 7-Deazapurine Nucleosides.
August 2020, The Journal of organic chemistry,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis, Photophysical Properties, and Biological Profiling of Benzothieno-Fused 7-Deazapurine Ribonucleosides.
June 2020, The Journal of organic chemistry,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis and Cytostatic and Antiviral Profiling of Thieno-Fused 7-Deazapurine Ribonucleosides.
March 2017, Journal of medicinal chemistry,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis and Cytotoxic and Antiviral Profiling of Pyrrolo- and Furo-Fused 7-Deazapurine Ribonucleosides.
October 2018, Journal of medicinal chemistry,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis of Polycyclic Hetero-Fused 7-Deazapurine Heterocycles and Nucleosides through C-H Dibenzothiophenation and Negishi Coupling.
October 2022, Journal of the American Chemical Society,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis and Antitrypanosomal Activity of 6-Substituted 7-Methyl-7-deazapurine Nucleosides.
April 2021, ACS infectious diseases,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis and biological profiling of 6- or 7-(het)aryl-7-deazapurine 4'-C-methylribonucleosides.
December 2015, Bioorganic & medicinal chemistry,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Correction to "Synthesis and Cytotoxic and Antiviral Profiling of Pyrrolo- and Furo-Fused 7-Deazapurine Ribonucleosides".
February 2019, Journal of medicinal chemistry,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis and evaluation of 3'-fluorinated 7-deazapurine nucleosides as antikinetoplastid agents.
April 2021, European journal of medicinal chemistry,
Marianne Fleuti, and Tania Sanchez-Quirante, and Lenka Poštová Slavětínská, and Eva Tloušt'ová, and Michal Tichý, and Soňa Gurská, and Petr Džubák, and Marián Hajdúch, and Michal Hocek
Synthesis and Cytotoxic and Antiviral Activity Profiling of All-Four Isomeric Series of Pyrido-Fused 7-Deazapurine Ribonucleosides.
October 2020, Chemistry (Weinheim an der Bergstrasse, Germany),
Copied contents to your clipboard!