Synthesis of new 2′-β-C-methyl related triciribine analogues as anti-HCV agents

Smith, Kenneth L.; Lai, Vincent S.; Prigaro, Brett J.; Ding, Yili; Gunić, Esmir; Girardet, Jean‐Luc; Zhong, Weidong; Hong, Zhi; Lang, Stanley A.; An, Hongyu

doi:10.1016/j.bmcl.2004.04.067

Cited by 16 publications

(11 citation statements)

References 30 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The coupling reaction between 2-b-C-methyl-1,2,3,5-tetra-O-benzoyl-b-D D-ribofuranose (1) 6 and 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]-pyrimidine (2) 7 gave the key intermediate 3 in high yield in 5 g scale. A similar approach for the synthesis of compound 3 was reported recently, 8 however, that paper did not provided any solid evidence to support the structure of compound 3. During our studies, we found that, even starting from compounds 1 and 2 under different conditions, an isomer of compound 3 was isolated from the reaction mixture as a major product.…”

mentioning

confidence: 83%

Synthesis of 2′-β-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors

Ding

Hong

et al. 2005

Bioorganic & Medicinal Chemistry Letters

Self Cite

View full text Add to dashboard Cite

mentioning

confidence: 83%

Synthesis of 2′-β-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors

Ding

Hong

et al. 2005

Bioorganic & Medicinal Chemistry Letters

Self Cite

View full text Add to dashboard Cite

“…Simpler modifications of the 6-position such as in 15a,b showed low micromolar activity in the replicon assay [69]. Also 2'-C-methyl versions of the cyclic sangivamycin analog triciribine such as 16 were prepared by this group [70]. Also 2'-C-methyl versions of the cyclic sangivamycin analog triciribine such as 16 were prepared by this group [70].…”

Section: '-Modified Nucleoside Inhibitorsmentioning

confidence: 99%

Recent Progress in the Development of Inhibitors of the Hepatitis C Virus RNA-Dependent RNA Polymerase

Koch¹,

Narjes

2007

CTMC

105

View full text Add to dashboard Cite

The global prevalence of hepatitis C virus (HCV) infection and the serious consequences associated with the chronic state of the disease have become a worldwide health problem. A combination therapy comprising Interferon-alpha and Ribavirin represents the current standard treatment for chronic HCV infection, although it has demonstrated limited success and causes serious side effects. Promising alternative approaches toward the control of HCV infection include the development of small molecule inhibitors of viral enzymes interfering with the essential steps in the life cycle of the virus. In this review we will focus on inhibitors of the HCV-encoded NS5B RNA-dependent RNA polymerase (NS5B RdRp) which is essential for viral replication and has been recognized as a prime target for therapeutic intervention.

show abstract

“…Valeant Pharmaceuticals disclose several derivatives that demonstrate EC 50 s below 10 µM in a replicon assay and possess good therapeutic indexes, although none were as active as the simple adenosine-based prototype 266 [787][788][789]. However, a marked increase in the cell-based activity of 267 was accomplished by synthesizing a prodrug of the monophosphate derivative, 268, which is over 150-fold more potent than the progenitor [787].…”

Section: Nucleoside Inhibitors Of Hcv Ns5bmentioning

confidence: 99%

“…However, a marked increase in the cell-based activity of 267 was accomplished by synthesizing a prodrug of the monophosphate derivative, 268, which is over 150-fold more potent than the progenitor [787]. Triciribine analogues inhibit HCV replication in a replicon system with modest potency although in the closely related analogues 269 and 270, the 2'-C-methyl riboside is associated with reduced potency compared to the simple riboside [789].…”

Section: Nucleoside Inhibitors Of Hcv Ns5bmentioning

confidence: 99%

Developments in Antiviral Drug Design, Discovery and Development in 2004

Meanwell

Belema²,

Carini³

et al. 2005

CDTID

View full text Add to dashboard Cite

This article summarizes key aspects of progress made during 2004 toward the design, discovery and development of antiviral agents for clinical use. Important developments in the identification, characterization and clinical utility of inhibitors of human immunodeficiency virus; the hepatitis viruses, hepatitis B, hepatitis C; the herpes family of viruses, herpes simplex viruses 1 and 2, varicella zoster virus, Epstein-Barr virus and human cytomegalovirus; the respiratory viruses, influenza, respiratory syncytial virus, human metapneumovirus, picornaviruses, measles and the severe acute respiratory syndrome coronavirus; human papilloma virus; rotavirus; Ebola virus and West Nile virus, are reviewed.

show abstract

Synthesis of new 2′-β-C-methyl related triciribine analogues as anti-HCV agents

Cited by 16 publications

References 30 publications

Synthesis of 2′-β-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors

Synthesis of 2′-β-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors

Recent Progress in the Development of Inhibitors of the Hepatitis C Virus RNA-Dependent RNA Polymerase

Developments in Antiviral Drug Design, Discovery and Development in 2004

Contact Info

Product

Resources

About