Literature DB >> 17048848

Stereoselective synthesis of 2'-C-methyl-cyclopropyl-fused carbanucleosides as potential anti-HCV agents.

Jeong A Lee1, Hea Ok Kim, Dilip K Tosh, Hyung Ryong Moon, Sanghee Kim, Lak Shin Jeong.   

Abstract

Stereoselective synthesis of 2'-C-methyl-cyclopropyl-fused carbanucleosides was accomplished via stereoselective cyclopropanation, regioselective cleavage of the isopropylidene group, stereoselective Grignard reaction, and cyclic sulfate chemistry. [reaction: see text]

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Year:  2006        PMID： 17048848     DOI： 10.1021/ol061959f

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

1.  Methanocarba ring as a ribose modification in ligands of G protein-coupled purine and pyrimidine receptors: synthetic approaches.

Authors:  Dilip K Tosh; Kenneth A Jacobson
Journal:  Medchemcomm       Date:  2013-12-17       Impact factor: 3.597

Review 2.  Polypharmacology of conformationally locked methanocarba nucleosides.

Authors:  Kenneth A Jacobson; Dilip K Tosh; Kiran S Toti; Antonella Ciancetta
Journal:  Drug Discov Today       Date:  2017-08-03       Impact factor: 7.851

3.  Regio- and stereoselective synthesis of truncated 3'-aminocarbanucleosides and their binding affinity at the A3 adenosine receptor.

Authors:  Mun Ju Choi; Girish Chandra; Hyuk Woo Lee; Xiyan Hou; Won Jun Choi; Khai Phan; Kenneth A Jacobson; Lak Shin Jeong
Journal:  Org Biomol Chem       Date:  2011-08-23       Impact factor: 3.876

4.  Efficient, large-scale synthesis and preclinical studies of MRS5698, a highly selective A3 adenosine receptor agonist that protects against chronic neuropathic pain.

Authors:  Dilip K Tosh; Janak Padia; Daniela Salvemini; Kenneth A Jacobson
Journal:  Purinergic Signal       Date:  2015-06-27       Impact factor: 3.765

5.  Synthesis of enantiomerically pure (S)-methanocarbaribo uracil nucleoside derivatives for use as antiviral agents and P2Y receptor ligands.

Authors:  Artem Melman; Minghong Zhong; Victor E Marquez; Kenneth A Jacobson
Journal:  J Org Chem       Date:  2008-09-24       Impact factor: 4.354

6.  5'-O-masked 2'-deoxyadenosine analogues as lead compounds for hepatitis C virus (HCV) therapeutic agents.

Authors:  Masahiro Ikejiri; Takayuki Ohshima; Keizo Kato; Masaaki Toyama; Takayuki Murata; Kunitada Shimotohno; Tokumi Maruyama
Journal:  Bioorg Med Chem       Date:  2007-08-22       Impact factor: 3.641
  6 in total

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