title: Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides.
abstract: Carbocyclic C-nucleosides are quite rare. Our route enables flexible preparation of three classes of these nucleoside analogs from common precursors-properly substituted cyclopentanones, which can be prepared racemic (in six steps) or optically pure (in ten steps) from inexpensive norbornadiene. The methodology allows flexible manipulation of individual positions around the cyclopentane ring, namely highly diastereoselective installation of carbo- and heterocyclic substituents at position 1', orthogonal functionalization of position 5', and efficient inversion of stereochemistry at position 2'. Newly prepared carbocyclic C-analog of tubercidine, profiled in MCF7 (breast cancer) and HFF1 (human foreskin fibroblasts) cell cultures, is less potent than tubercidine itself, but more selectively toxic toward the tumorigenic cells.
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.|International Center for Clinical Research, St. Anne's University Hospital Brno , Pekařská 53, 656 91 Brno, Czech Republic.
authors.forename: Lukáš
authors.initials: L
authors.lastname: Maier
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.|International Center for Clinical Research, St. Anne's University Hospital Brno , Pekařská 53, 656 91 Brno, Czech Republic.
authors.forename: Prashant
authors.initials: P
authors.lastname: Khirsariya
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.|International Center for Clinical Research, St. Anne's University Hospital Brno , Pekařská 53, 656 91 Brno, Czech Republic.
authors.forename: Ondřej
authors.initials: O
authors.lastname: Hylse
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.
authors.forename: Santosh Kumar
authors.initials: SK
authors.lastname: Adla
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.
authors.forename: Lenka
authors.initials: L
authors.lastname: Černová
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.
authors.forename: Michal
authors.initials: M
authors.lastname: Poljak
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.
authors.forename: Soňa
authors.initials: S
authors.lastname: Krajčovičová
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.
authors.forename: Erik
authors.initials: E
authors.lastname: Weis
authors.affiliation: Department of Cytokinetics, Institute of Biophysics, Academy of Sciences of the Czech Republic , Královopolská 135, 612 00 Brno, Czech Republic.
authors.forename: Stanislav
authors.initials: S
authors.lastname: Drápela
authors.affiliation: International Center for Clinical Research, St. Anne's University Hospital Brno , Pekařská 53, 656 91 Brno, Czech Republic.|Department of Cytokinetics, Institute of Biophysics, Academy of Sciences of the Czech Republic , Královopolská 135, 612 00 Brno, Czech Republic.
authors.forename: Karel
authors.initials: K
authors.lastname: Souček
authors.affiliation: Department of Chemistry, CZ Openscreen, Faculty of Science, Masaryk University , Kamenice 5/A8, 625 00 Brno, Czech Republic.|International Center for Clinical Research, St. Anne's University Hospital Brno , Pekařská 53, 656 91 Brno, Czech Republic.
authors.forename: Kamil
authors.identifier: 0000-0001-9502-3173
authors.initials: K
authors.lastname: Paruch
mesh_terms: D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D003517:Cyclopentanes; D009705:Nucleosides