The use of the system CF3SO2Na/tert-butyl-hydroperoxide (tert-ButOOH), recently reported for the efficient trifluoromethylation of a variety of heterocyclic aromatic compounds, has been here profitably exploited for the synthesis of 5-CF3-2'-deoxycytidine, 8-CF3-2'-deoxyadenosine, 8-CF3-2'-deoxyguanosine and 8-CF3- inosine, regioselectively obtained in good to acceptable yields following a very simple protocol. The bioactivity of these modified nucleosides, and particularly of the novel 8-CF3-20-deoxyguanosine and 8- CF3-inosine, has been evaluated on a panel of tumour and non-tumour cell lines in preliminary in vitro cytotoxicity assays.
Trifluoromethyl derivatives of canonical nucleosides: synthesis and bioactivity studies / Musumeci, Domenica; Irace, Carlo; Santamaria, Rita; Montesarchio, Daniela. - In: MEDCHEMCOMM. - ISSN 2040-2503. - 4:10(2013), pp. 1405-1410. [10.1039/c3md00159h]
Trifluoromethyl derivatives of canonical nucleosides: synthesis and bioactivity studies
MUSUMECI, DOMENICA;IRACE, CARLO;SANTAMARIA, RITA;MONTESARCHIO, DANIELA
2013
Abstract
The use of the system CF3SO2Na/tert-butyl-hydroperoxide (tert-ButOOH), recently reported for the efficient trifluoromethylation of a variety of heterocyclic aromatic compounds, has been here profitably exploited for the synthesis of 5-CF3-2'-deoxycytidine, 8-CF3-2'-deoxyadenosine, 8-CF3-2'-deoxyguanosine and 8-CF3- inosine, regioselectively obtained in good to acceptable yields following a very simple protocol. The bioactivity of these modified nucleosides, and particularly of the novel 8-CF3-20-deoxyguanosine and 8- CF3-inosine, has been evaluated on a panel of tumour and non-tumour cell lines in preliminary in vitro cytotoxicity assays.File | Dimensione | Formato | |
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