Diastereoselective Flexible Synthesis of Carbocyclic C-Nucleosides
| Autor: | Stanislav Drápela, Karel Souček, Erik Weis, Kamil Paruch, PrashantKumar Khirsariya, Michal Poljak, Santosh Kumar Adla, Ondřej Hylse, Soňa Krajčovičová, Lukáš Maier, Lenka Černová |
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| Rok vydání: | 2017 |
| Předmět: |
Antitumor activity
Molecular Structure 010405 organic chemistry Chemistry Stereochemistry Norbornadiene Organic Chemistry Nucleosides Stereoisomerism Cyclopentanes 010402 general chemistry Ring (chemistry) 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Humans C nucleosides Cyclopentane Cells Cultured Cell Proliferation |
| Zdroj: | The Journal of Organic Chemistry. 82:3382-3402 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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