250658-12-9Relevant articles and documents
Nitroxide-labeled pyrimidines for non-covalent spin-labeling of abasic sites in DNA and RNA duplexes
Shelke, Sandip A.,Sandholt, Gunnar B.,Sigurdsson, Snorri Th.
, p. 7366 - 7374 (2014)
Non-covalent and site-directed spin labeling gives easy access to spin-labeled nucleic acids for the study of their structure and dynamics by electron paramagnetic resonance (EPR) spectroscopy. In a search for improved spin labels for non-covalent binding to abasic sites in duplex DNA and RNA, ten pyrimidine-derived spin labels were prepared in good yields and their binding was evaluated by continuous wave (CW)-EPR spectroscopy. Most of the spin labels showed lower binding affinity than the previously reported label c towards abasic sites in DNA and RNA. The most promising labels were triazole-linked spin labels and a pyrrolocytosine label. In particular, the N1-ethylamino derivative of a triazole-linked uracil spin label binds fully to both DNA and RNA containing an abasic site. This is the first example of a spin label that binds fully through non-covalent interactions with an abasic site in RNA. This journal is the Partner Organisations 2014.
Synthesis and biological evaluation of 6-(alkyn-1-yl)furo[2,3-d]pyrimidin- 2(3H)-one base and nucleoside derivatives
Robins, Morris J.,Miranda, Karl,Rajwanshi, Vivek K.,Peterson, Matt A.,Andrei, Graciela,Snoeck, Robert,De Clercq, Erik,Balzarini, Jan
, p. 391 - 398 (2007/10/03)
Derivatives of the 2′-deoxynucleoside of furo[2,3-d]pyrimidin-2(3H)- one with long-chain alkyl (or 4-alkylphenyl) substituents at C6 exhibit remarkable anti-VZV (varicella-zoster virus) potency and selectivity, and analogous 2′,3′-dideoxynucleoside derivatives show anti-HCMV (human cytomegalovirus) activity. We now report a synthetic approach that enables the preparation of long-chain 6-(alkyn-1-yl)furo[2,3-d]pyrimidin-2(3H)-ones in which the rodlike acetylene spacer replaces the 4-substituted-phenyl ring at C6. Analogues with methyl, β-D-ribofuranosyl, β-D-arabinofuranosyl, and 2-deoxy-β-D-erythro-pentofuranosyl substituents at N3 have been prepared. Long-chain derivatives at C6 in the 2′-deoxynucleoside series showed virus-encoded nucleoside kinase-sensitive anti-VZV activity. Surprisingly, 3-methyl-6-(octyn-1-yl)furo[2,3-d]-pyrimidin-2(3H)-one (prepared as a negative anti-VZV test control) exhibited anti-HCMV activity, which supports the possibility of development of non-nucleoside anti-HCMV agents originating from uncomplicated derivatives of such bicyclic ring systems.
