2017
Maier, Lukáš; Khirsariya, Prashant; Hylse, Ondřej; Adla, Santosh Kumar; Černová, Lenka; Poljak, Michal; Krajčovičová, Soňa; Weis, Erik; Drápela, Stanislav; Souček, Karel; Paruch, Kamil
Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides. Journal Article
In: The Journal of organic chemistry, vol. 82, no. 7, pp. 3382–3402, 2017, ISSN: 1520-6904 0022-3263, (Place: United States).
Abstract | Links | BibTeX | Tags: Cell Proliferation/drug effects, Cells, Cultured, Cyclopentanes/chemical synthesis/chemistry/*pharmacology, Humans, Molecular Structure, Nucleosides/chemical synthesis/chemistry/*pharmacology, Stereoisomerism
@article{maier_diastereoselective_2017,
title = {Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides.},
author = {Lukáš Maier and Prashant Khirsariya and Ondřej Hylse and Santosh Kumar Adla and Lenka Černová and Michal Poljak and Soňa Krajčovičová and Erik Weis and Stanislav Drápela and Karel Souček and Kamil Paruch},
doi = {10.1021/acs.joc.6b02594},
issn = {1520-6904 0022-3263},
year = {2017},
date = {2017-04-01},
journal = {The Journal of organic chemistry},
volume = {82},
number = {7},
pages = {3382–3402},
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.},
note = {Place: United States},
keywords = {Cell Proliferation/drug effects, Cells, Cultured, Cyclopentanes/chemical synthesis/chemistry/*pharmacology, Humans, Molecular Structure, Nucleosides/chemical synthesis/chemistry/*pharmacology, Stereoisomerism},
pubstate = {published},
tppubtype = {article}
}
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.