367259-52-7Relevant academic research and scientific papers
Potent 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid-based macrocyclic inhibitors of hepatitis C virus NS3 protease
Chen, Kevin X.,Njoroge, F. George,Pichardo, John,Prongay, Andrew,Butkiewicz, Nancy,Yao, Nanhua,Madison, Vincent,Girijavallabhan, Viyyoor
, p. 567 - 574 (2007/10/03)
The NS3 protease of hepatitis C virus (HCV) has emerged as one of the best characterized targets for next-generation HCV therapy. The tetrapeptide 1 and pentapeptide 2 are α-ketoamide-type HCV serine protease inhibitors with modest potency. We envisioned
Novel potent hepatitis C virus NS3 serine protease inhibitors derived from proline-based macrocycles
Chen, Kevin X.,Njoroge, F. George,Arasappan, Ashok,Venkatraman, Srikanth,Vibulbhan, Bancha,Yang, Weiying,Parekh, Tejal N.,Pichardo, John,Prongay, Andrew,Cheng, Kuo-Chi,Butkiewicz, Nancy,Yao, Nanhua,Madison, Vincent,Girijavallabhan, Viyyoor
, p. 995 - 1005 (2007/10/03)
The hepatitis C virus (HCV) NS3 protease is essential for viral replication. It has been a target of choice for intensive drug discovery research. On the basis of an active pentapeptide inhibitor, 1, we envisioned that macrocyclization from the P2 proline
Design, synthesis, and biological activity of m-tyrosine-based 16- and 17-membered macrocyclic inhibitors of hepatitis C virus NS3 serine protease
Chen, Kevin X.,Njoroge, F. George,Pichardo, John,Prongay, Andrew,Butkiewicz, Nancy,Yao, Nanhua,Madison, Vincent,Girijavallabhan, Viyyoor
, p. 6229 - 6235 (2007/10/03)
The limited efficacy and considerable side effects of currently available therapies for the treatment of hepatitis C virus (HCV) infection have prompted significant efforts toward the development of safe and effective new therapeutics. The pentapeptide α-
Design and synthesis of depeptidized macrocyclic inhibitors of hepatitis C NS3-4A protease using structure-based drug design
Venkatraman, Srikanth,Njoroge, F. George,Girijavallabhan, Viyyoor M.,Madison, Vincent S.,Yao, Nanua H.,Prongay, Andrew J.,Butkiewicz, Nancy,Pichardo, John
, p. 5088 - 5091 (2007/10/03)
Hepatitus C virus (HCV) NS3, when bound to NS4A cofactor, facilitates development of mature virons by catalyzing cleavage of a polyprotein to form functional and structural proteins of HCV. The enzyme has a shallow binding pocket at the catalytic site, ma
Synthesis and biological activity of macrocyclic inhibitors of hepatitis C virus (HCV) NS3 protease
Chen, Kevin X.,Njoroge, F. George,Prongay, Andrew,Pichardo, John,Madison, Vincent,Girijavallabhan, Viyyoor
, p. 4475 - 4478 (2007/10/03)
The 17-membered phenylalanine-based macrocycle 6 was prepared starting from 3-iodo-phenylalanine. Macrocyclization of alkene phenyl iodide 5 was effected through a palladium-catalyzed Heck reaction. The macrocyclic α-ketoamides were active inhibitors of t
Proline-based macrocyclic inhibitors of the hepatitis C virus: Stereoselective synthesis and biological activity
Chen, Kevin X.,Njoroge, F. George,Vibulbhan, Bancha,Prongay, Andrew,Pichardo, John,Madison, Vincent,Buevich, Alexei,Chan, Tze-Ming
, p. 7024 - 7028 (2007/10/03)
Life-saving donut: Macrocyclization through a Mitsunobu reaction was used to synthesize a 17-membered macrocycle. The bicyclic acetal core was prepared completely diastereoselectively. The macrocyclic peptidomimetic surrogate of the P2-P3 dipeptide moiety was designed to function as a hepatitis C virus (HCV) NS3 serine protease inhibitor, and the pentapeptide α-ketoamides derived from the macrocycle were shown to be potent HCV inhibitors. (Figure Presented).
