52450-18-7Relevant articles and documents
A novel synthesis and biological activity of several 5-halo-5'-amino analogues of deoxyribopyrimidine nucleosides.
Lin,Prusoff
, p. 106 - 109 (1978)
A novel synthetic procedure has been developed for the large-scale synthesis of 5-chloro-, 5-bromo-, and 5-iodo-5'-amino-2',5'-dideoxyuridine (4c-e) as well as of two new analogues, 5-iodo-5'-amino-2',5'-dideoxycytidine and 5-fluoro-5'-amino-2',5'-dideoxyuridine (4a and 4b), in good yield. The starting materials, 5-halo-2'-deoxyuridine and 5-halo-2'-deoxycytidine, are readily available and the method is straightforward. This report describes the synthesis and the biologial activities of these compounds.
Stereoselective Syntheses of 3-Hydroxyamino- A nd 3-Methoxyamino-2,3-Dideoxynucleosides
Bose, Sritama,Hodgson, David R. W.
, p. 9084 - 9088 (2019)
Aminonucleosides are used as key motifs in medicinal and bioconjugate chemistry; however, existing strategies toward 3-hypernucleophilic amine systems do not readily deliver deoxyribo-configured products. We report diastereoselective syntheses of deoxyribo- A nd deoxyxylo-configured 3-hydroxyamino- A nd 3-methoxyamino-nucelosides from 3-imine intermediates. The presence or absence of the 5-hydroxyl-group protection dictates facial selectivity via inter-or intramolecular delivery of hydride from BH3 (borane). Protecting group screening gave one access to previously unknown 3-methoxyamino-deoxyguanosine derivatives.
Antiviral activities of β-enantiomers of 3′-substituted-3′-deoxythymidine analogs
Faraj, Abdesslem,Alaoui, M. Abdelaziz El,Pavia, Geraldine,Gosselin, Gilles,Imbach, Jean-Louis,Schinazi, Raymond F.,Sommadossi, Jean Pierre
, p. 1287 - 1290 (1997)
Several β-L-3′-substituted-3′-deoxythymidine were stereospecifically synthesized. None of these analogs inhibited HIV-1 nor HBV replication in vitro suggesting that these β-L-pyrimidine derivatives may not be efficiently phosphorylated inside the cells Copyright
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Lin et al.
, p. 130 (1978)
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Probing the binding requirements of modified nucleosides with the dna nuclease snm1a
Dürr, Eva-Maria,McGouran, Joanna F.
, (2021/06/21)
SNM1A is a nuclease that is implicated in DNA interstrand crosslink repair and, as such, its inhibition is of interest for overcoming resistance to chemotherapeutic crosslinking agents. However, the number and identity of the metal ion(s) in the active site of SNM1A are still unconfirmed, and only a limited number of inhibitors have been reported to date. Herein, we report the synthesis and evaluation of a family of malonate-based modified nucleosides to investigate the optimal positioning of metal-binding groups in nucleoside-derived inhibitors for SNM1A. These compounds include ester, carboxylate and hydroxamic acid malonate derivatives which were installed in the 5′-position or 3′-position of thymidine or as a linkage between two nucleosides. Evaluation as inhibitors of recombinant SNM1A showed that nine of the twelve compounds tested had an inhibitory effect at 1 mM concentration. The most potent compound contains a hydroxamic acid malonate group at the 5′-position. Overall, our studies advance the understanding of requirements for nucleoside-derived inhibitors for SNM1A and indicate that groups containing a negatively charged group in close proximity to a metal chelator, such as hydroxamic acid malonates, are promising structures in the design of inhibitors.
