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Phenylglycine as a ...
Phenylglycine as a Novel P2 Scaffold in Hepatitis C Virus NS3 Protease Inhibitors
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- Örtqvist, Pernilla (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Peterson, Shane D. (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Åkerblom, Eva (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Gossas, Thomas (author)
- Uppsala universitet,Institutionen för naturvetenskaplig biokemi
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- Sabnis, Yogesh A. (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Fransson, Rebecca (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Lindeberg, Gunnar (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Danielson, U. Helena (author)
- Uppsala universitet,Institutionen för naturvetenskaplig biokemi
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- Karlén, Anders (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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- Sandström, Anja (author)
- Uppsala universitet,Avdelningen för organisk farmaceutisk kemi
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(creator_code:org_t)
- Elsevier BV, 2007
- 2007
- English.
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In: Bioorganic & Medicinal Chemistry. - : Elsevier BV. - 0968-0896 .- 1464-3391. ; 15:3, s. 1448-1474
- Related links:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Subject headings
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- Molecular modeling and inhibitory potencies of tetrapeptide protease inhibitors of HCV NS3 proposed phenylglycine as a new promising P2 residue. The results suggest that phenylglycine might be capable of interacting with the NS3 (protease-helicase/NTPase) in ways not possible for the common P2 proline-based inhibitors. Thus, a series of tripeptides, both linear and macrocyclic, based on p-hydroxy-phenylglycine in the P2 position were prepared and their inhibitory effect determined. When the p-hydroxy group was replaced by methoxy, isoquinolin-, or quinolinyloxy functions, inhibitors with improved potencies were obtained. The P2 phenylglycine-based inhibitors were further optimized by C-terminal extension to acyl sulfonamides and by P1–P3 cyclization, which gave products with inhibition constants in the nanomolar range (75 nM).
Subject headings
- MEDICIN OCH HÄLSOVETENSKAP -- Medicinska och farmaceutiska grundvetenskaper -- Farmaceutiska vetenskaper (hsv//swe)
- MEDICAL AND HEALTH SCIENCES -- Basic Medicine -- Pharmaceutical Sciences (hsv//eng)
Keyword
- HCV
- Phenylglycine
- Protease inhibitor
- Acyl sulfonamide
- PHARMACY
- FARMACI
Publication and Content Type
- ref (subject category)
- art (subject category)
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- By the author/editor
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Örtqvist, Pernil ...
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Peterson, Shane ...
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Åkerblom, Eva
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Gossas, Thomas
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Sabnis, Yogesh A ...
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Fransson, Rebecc ...
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show more...
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Lindeberg, Gunna ...
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Danielson, U. He ...
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Karlén, Anders
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Sandström, Anja
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- About the subject
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- MEDICAL AND HEALTH SCIENCES
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MEDICAL AND HEAL ...
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and Basic Medicine
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and Pharmaceutical S ...
- Articles in the publication
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Bioorganic & Med ...
- By the university
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Uppsala University