Proline-Based Macrocyclic Inhibitors of the Hepatitis C Virus: Stereoselective Synthesis and Biological Activity

2005 ◽  
Vol 117 (43) ◽  
pp. 7186-7190 ◽  
Author(s):  
Kevin X. Chen ◽  
F. George Njoroge ◽  
Bancha Vibulbhan ◽  
Andrew Prongay ◽  
John Pichardo ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Stereoselective Synthesis

Proline-Based Macrocyclic Inhibitors of the Hepatitis C Virus: Stereoselective Synthesis and Biological Activity

2005 ◽  
Vol 44 (43) ◽  
pp. 7024-7028 ◽  
Author(s):  
Kevin X. Chen ◽  
F. George Njoroge ◽  
Bancha Vibulbhan ◽  
Andrew Prongay ◽  
John Pichardo ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Stereoselective Synthesis

Discovery of novel HCV inhibitors: Synthesis and biological activity of 6-(indol-2-yl)pyridine-3-sulfonamides targeting hepatitis C virus NS4B

2013 ◽  
Vol 23 (13) ◽  
pp. 3947-3953 ◽  
Author(s):  
Xiaoyan Zhang ◽  
Nanjing Zhang ◽  
Guangming Chen ◽  
Anthony Turpoff ◽  
Hongyu Ren ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C

Synthesis and Biological Activity of Macrocyclic Inhibitors of Hepatitis C Virus (HCV) NS3 Protease.

ChemInform ◽  
2006 ◽  
Vol 37 (2) ◽  
Author(s):  
Kevin X. Chen ◽  
F. George Njoroge ◽  
Andrew Prongay ◽  
John Pichardo ◽  
Vincent Madison ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Ns3 Protease

Synthesis and Biological Activity of 1H-benzotriazole and 1H-benzimidazole Analogues — Inhibitors of the NTPase/Helicase of HCV and of Some Related Flaviviridae

2005 ◽  
Vol 16 (5) ◽  
pp. 315-326 ◽  
Author(s):  
Maria Bretner ◽  
Andrea Baier ◽  
Katarzyna Kopańska ◽  
Andżelika Najda ◽  
Anna Schoof ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Inhibitory Activity ◽  
Alkylating Agents ◽  
Alkyl Halides ◽  
Helicase Activity ◽  
Alkyl Derivatives ◽  
Flash Column Chromatography ◽  
Derivatives Of

To improve anti-helical activity of analogues of 1 H-benzotriazole and 1 H-benzimidazole their N-alkyl derivatives were synthesized and tested for anti-helicase activity against enzymes of selected Flaviviridae including hepatitis C virus (HCV), West Nile virus (WNV), Dengue virus (DENV) and Japanese encephalitis virus (JEV). 1- and 2-alkyl derivatives of 4,5,6,7-tetrabromo-1 H-benzotriazole were obtained by direct alkylation of 4,5,6,7-tetrabromo-1 H-benzotriazole with the use of respective alkyl halides in the presence of KOH in methanol, to give a mixture of 1- and 2- isomers, which was separated by flash column chromatography in good yield. The proportion of isomers strongly depended on the reaction time and temperature. 1- and 2-hydroxyethyl and 1- and 2-chloroethyl derivatives of the tetrabromobenzo-triazole were synthesized with the use of 2-bromoethanol and 1-bromo-2-chloroethane respectively as alkylating agents. N-alkylation of this benzotriazole compound enhanced inhibitory activity and selectivity towards the helicase activity of HCV NTPase/helicase. The most active were the 2-methyl, 2-ethyl and 2-propyl derivatives (IC50∼6.5 μM in the presence of DNA as a substrate). Derivatives of the benzotriazole in which hydroxyethyl or chloroethyl replaced the alkyl substituents lost their inhibitory activity. Brominated or methylated benzotriazole N(1) ribosides also did not exert helicase inhibitory activity. Although a number of N(1) and N(2) alkyl derivatives exerted good HCV and WNV helicase inhibitory activity when DNA was used as substrate, the activity was strongly decreased or even disappeared when RNA was used as substrate. The cytotoxicity tests in Vero and HeLa Tat cells showed a substantial decrease of cytotoxicity of N-alkyl derivatives as compared to the parent benzotriazole.

Design, Synthesis, and Biological Activity ofm-Tyrosine-Based 16- and 17-Membered Macrocyclic Inhibitors of Hepatitis C Virus NS3 Serine Protease

2005 ◽  
Vol 48 (20) ◽  
pp. 6229-6235 ◽  
Author(s):  
Kevin X. Chen ◽  
F. George Njoroge ◽  
John Pichardo ◽  
Andrew Prongay ◽  
Nancy Butkiewicz ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Serine Protease ◽  
Design Synthesis

Synthesis and Biological Activity of 5′,9-Anhydro-3-purine-isonucleosides as Potential anti-Hepatitis C Virus Agents.

ChemInform ◽  
2007 ◽  
Vol 38 (21) ◽  
Author(s):  
Byoung-Kwon Chun ◽  
Peiyuan Wang ◽  
Abdalla Hassan ◽  
Jinfa Du ◽  
Phillip M. Tharnish ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C

Synthesis and biological activity of macrocyclic inhibitors of hepatitis C virus (HCV) NS3 protease

2005 ◽  
Vol 15 (20) ◽  
pp. 4475-4478 ◽  
Author(s):  
Kevin X. Chen ◽  
F. George Njoroge ◽  
Andrew Prongay ◽  
John Pichardo ◽  
Vincent Madison ◽  
...  
Keyword(s):  
Biological Activity ◽  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Ns3 Protease

scholarly journals Stereoselective Synthesis and Biological Evaluations of Novel 3′-Deoxy-4′-azaribonucleosides as Inhibitors of Hepatitis C Virus RNA Replication

2009 ◽  
Vol 52 (13) ◽  
pp. 4054-4057 ◽  
Author(s):  
Ugo Chiacchio ◽  
Luisa Borrello ◽  
Lia Crispino ◽  
Antonio Rescifina ◽  
Pedro Merino ◽  
...  
Keyword(s):  
Hepatitis C Virus ◽  
Hepatitis C ◽  
Stereoselective Synthesis ◽  
Rna Replication ◽  
Hepatitis C Virus Rna ◽  
Virus Rna
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