- Synthesis of a 6-methyl-7-deaza analogue of adenosine that potently inhibits replication of polio and dengue viruses
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Bioisosteric deaza analogues of 6-methyl-9-β-d-ribofuranosylpurine, a hydrophobic analogue of adenosine, were synthesized and evaluated for antiviral activity. Whereas the 1-deaza and 3-deaza analogues were essentially inactive in plaque assays of infectivity, a novel 7-deaza-6-methyl-9-β-d- ribofuranosylpurine analogue, structurally related to the natural product tubercidin, potently inhibited replication of poliovirus (PV) in HeLa cells (IC50 = 11 nM) and dengue virus (DENV) in Vero cells (IC50 = 62 nM). Selectivity against PV over cytotoxic effects to HeLa cells was >100-fold after incubation for 7 h. Mechanistic studies of the 5′-triphosphate of 7-deaza-6-methyl-9-β-d-ribofuranosylpurine revealed that this compound is an efficient substrate of PV RNA-dependent RNA polymerase (RdRP) and is incorporated into RNA mimicking both ATP and GTP.
- Wu, Runzhi,Smidansky, Eric D.,Oh, Hyung Suk,Takhampunya, Ratree,Padmanabhan, Radhakrishnan,Cameron, Craig E.,Peterson, Blake R.
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experimental part
p. 7958 - 7966
(2011/03/19)
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- An alternate route to 2-amino-3-nitro-5-bromo-4-picoline: Regioselective pyridine synthesis via 2-nitramino-picoline intermediate
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The 2-nitramino functionality in 2-nitramino-4-picoline was successfully exploited not only as a protecting group but also as a directional handle to afford an efficient, atom-economic, and regioselective synthesis of 2-amino-5-bromo-3-nitro-4-picoline (4), a precursor for a drug candidate in development.
- Bhattacharya, Apurba,Purohit, Vikram C.,Deshpande, Prashant,Pullockaran, Annie,Grosso, John A.,DiMarco, John D.,Gougoutas, Jack Z.
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p. 885 - 888
(2012/12/30)
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- Method of preparation of nitroaminopyridine compounds
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A method of preparing an intermediate which is useful for the preparation of azaindole derivatives.
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Page/Page column 2; 3
(2008/06/13)
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