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  • Lampa, AnnaUppsala universitet,Avdelningen för organisk farmaceutisk kemi (author)

Improved P2 phenylglycine-based hepatitis C virus NS3 protease inhibitors with alkenylic prime-side substituents

  • Article/chapterEnglish2010

Publisher, publication year, extent ...

  • Elsevier BV,2010
  • printrdacarrier

Numbers

  • LIBRIS-ID:oai:DiVA.org:uu-129431
  • https://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-129431URI
  • https://doi.org/10.1016/j.bmc.2010.05.027DOI

Supplementary language notes

  • Language:English
  • Summary in:English

Part of subdatabase

Classification

  • Subject category:ref swepub-contenttype
  • Subject category:art swepub-publicationtype

Notes

  • Phenylglycine has proved to be a useful P2 residue in HCV NS3 protease inhibitors. A novel pi-pi-interaction between the phenylglycine and the catalytic H57 residue of the protease is postulated. We hypothesized that the introduction of a vinyl on the phenylglycine might strengthen this pi-pi-interaction. Thus, herein is presented the synthesis and inhibitory potency of a series of acyclic vinylated phenylglycine-based HCV NS3 protease inhibitors. Surprisingly, inhibitors based on both D- and L-phenylglycine were found to be effective inhibitors, with a slight preference for the d-epimers. Furthermore, prime-side alkenylic extension of the C-terminal acylsulfonamide group gave significantly improved inhibitors with potencies in the nanomolar range (approximately 35 nM), potencies which were retained on mutant variants of the protease.

Subject headings and genre

  • HCV
  • Protease inhibitors
  • Peptidomimetics
  • Phenylglycine
  • Resistance
  • Alkenylic acylsulfonamides
  • PHARMACY
  • FARMACI
  • NATURAL SCIENCES
  • NATURVETENSKAP

Added entries (persons, corporate bodies, meetings, titles ...)

  • Ehrenberg, Angelica E.Uppsala universitet,Biokemi (author)
  • Gustafsson, Sofia S.Uppsala universitet,Biokemi(Swepub:uu)sofsv946 (author)
  • Vema, AparnaUppsala universitet,Avdelningen för organisk farmaceutisk kemi (author)
  • Åkerblom, EvaUppsala universitet,Avdelningen för organisk farmaceutisk kemi(Swepub:uu)eak28141 (author)
  • Lindeberg, GunnarUppsala universitet,Avdelningen för organisk farmaceutisk kemi(Swepub:uu)gunnlind (author)
  • Karlén, AndersUppsala universitet,Avdelningen för organisk farmaceutisk kemi(Swepub:uu)anderskl (author)
  • Danielson, U. HelenaUppsala universitet,Biokemi(Swepub:uu)helenads (author)
  • Sandström, AnjaUppsala universitet,Avdelningen för organisk farmaceutisk kemi(Swepub:uu)anjajoha (author)
  • Uppsala universitetAvdelningen för organisk farmaceutisk kemi (creator_code:org_t)

Related titles

  • In:Bioorganic & Medicinal Chemistry: Elsevier BV18:14, s. 5413-54240968-08961464-3391

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