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Synthesis and characterization of 2′-C-Me branched C-nucleosides as HCV polymerase inhibitors

Cho, Aesop ; Zhang, Lijun ; Xu, Jie ; Babusis, Darius ; Butler, Thomas ; Lee, Rick ; Saunders, Oliver L. ; Wang, Ting ; Parrish, Jay ; Perry, Jason ; Feng, Joy Y. ; Ray, Adrian S. ; Kim, Choung U.

Bioorganic & medicinal chemistry letters, 2012-06, Vol.22 (12), p.4127-4132 [Periódico revisado por pares]

Amsterdam: Elsevier Ltd

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Título:
Synthesis and characterization of 2′-C-Me branched C-nucleosides as HCV polymerase inhibitors
Autor: Cho, Aesop ; Zhang, Lijun ; Xu, Jie ; Babusis, Darius ; Butler, Thomas ; Lee, Rick ; Saunders, Oliver L. ; Wang, Ting ; Parrish, Jay ; Perry, Jason ; Feng, Joy Y. ; Ray, Adrian S. ; Kim, Choung U.
Assuntos: Administration, Oral ; Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - pharmacokinetics ; Antiviral Agents - pharmacology ; antiviral properties ; Aza Compounds - chemical synthesis ; Aza Compounds - pharmacokinetics ; Aza Compounds - pharmacology ; Biological and medical sciences ; C-Nucleoside ; Cell Line ; Cricetinae ; Dogs ; enzyme inhibitors ; HCV ; Hepacivirus - drug effects ; Hepacivirus - enzymology ; Hepacivirus - growth & development ; Hepatitis C virus ; Hepatocytes - drug effects ; Hepatocytes - virology ; Humans ; in vitro studies ; in vivo studies ; Injections, Intravenous ; Medical sciences ; pharmacokinetics ; Pharmacology. Drug treatments ; Polymerase inhibitor ; Primary Cell Culture ; Purine Nucleosides - chemical synthesis ; Purine Nucleosides - pharmacokinetics ; Purine Nucleosides - pharmacology ; purine nucleotides ; pyrimidine nucleosides ; Pyrimidine Nucleosides - chemical synthesis ; Pyrimidine Nucleosides - pharmacokinetics ; Pyrimidine Nucleosides - pharmacology ; Rats ; RNA-Dependent RNA Polymerase - antagonists & inhibitors ; RNA-Dependent RNA Polymerase - metabolism ; RNA-directed RNA polymerase ; structure-activity relationships ; Viral Nonstructural Proteins - antagonists & inhibitors ; Viral Nonstructural Proteins - metabolism
É parte de: Bioorganic & medicinal chemistry letters, 2012-06, Vol.22 (12), p.4127-4132
Notas: http://dx.doi.org/10.1016/j.bmcl.2012.04.065
Descrição: A series of 2′-C-methyl branched purine and pyrimidine C-nucleosides were prepared. Their anti-HCV activity and pharmacological properties were profiled, and compared with known 2′-C-Me N-nucleoside counterparts. In particular, 2′-C-Me 4-aza-7,9-dideazaadenosine C-nucleoside (2) was found to have potent and selective anti-HCV activity in vitro as well as a favorable pharmacokinetic profile and in vivo potential for enhanced potency over the corresponding N-nucleoside. A series of 2′-C-methyl branched purine and pyrimidine C-nucleosides were prepared. Their anti-HCV activity and pharmacological properties were profiled, and compared with known 2′-C-Me N-nucleoside counterparts. In particular, 2′-C-Me 4-aza-7,9-dideazaadenosine C-nucleoside (2) was found to have potent and selective anti-HCV activity in vitro as well as a favorable pharmacokinetic profile and in vivo potential for enhanced potency over the corresponding N-nucleoside.
Editor: Amsterdam: Elsevier Ltd
Idioma: Inglês

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Synthesis and characterization of 2′-C-Me branched C-nucleosides as HCV polymerase inhibitors

Cho, Aesop ; Zhang, Lijun ; Xu, Jie ; Babusis, Darius ; Butler, Thomas ; Lee, Rick ; Saunders, Oliver L. ; Wang, Ting ; Parrish, Jay ; Perry, Jason ; Feng, Joy Y. ; Ray, Adrian S. ; Kim, Choung U.

Amsterdam: Elsevier Ltd

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