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  • Chorell, ErikUmeå universitet,Kemiska institutionen (author)

Synthesis and application of a bromomethyl substituted scaffold to be used for efficient optimization of anti-virulence activity

  • Article/chapterEnglish2011

Publisher, publication year, extent ...

  • Elsevier Masson SAS,2011
  • printrdacarrier

Numbers

  • LIBRIS-ID:oai:DiVA.org:umu-43916
  • https://urn.kb.se/resolve?urn=urn:nbn:se:umu:diva-43916URI
  • https://doi.org/10.1016/j.ejmech.2011.01.025DOI

Supplementary language notes

  • Language:English
  • Summary in:English

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

Notes

  • Pilicides are a class of compounds that attenuate virulence in Gram negative bacteria by blocking the chaperone/usher pathway in Escherichia coli. It has also been shown that compounds derived from the peptidomimetic scaffold that the pilicides are based on can prevent both Aβ aggregation and curli formation. To facilitate optimizations towards the different targets, a new synthetic platform has been developed that enables fast and simple introduction of various substituents in position C-7 on the peptidomimetic scaffold. Importantly, this strategy also enables introduction of previously unattainable heteroatoms in this position. Pivotal to the synthetic strategy is the synthesis of a C-7 bromomethyl substituted derivative of the ring-fused dihydrothiazolo 2-pyridone pilicide scaffold. From this versatile and reactive intermediate various heteroatom-linked substituents could be introduced on the scaffold including amines, ethers, amides and sulfonamides. In addition, carbon-carbon bonds could be introduced to the sp(3)-hybridized bromomethyl substituted scaffold by Suzuki-Miyaura cross couplings. Evaluation of the 24 C-7 substituted compounds in whole-bacterial assays provided important structure-activity data and resulted in the identification of a number of new pilicides with activity as good or better than those developed previously.

Subject headings and genre

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

  • Bengtsson, ChristofferUmeå universitet,Kemiska institutionen(Swepub:umu)chrben00 (author)
  • Sainte-Luce Banchelin, ThomasUmeå universitet,Kemiska institutionen(Swepub:umu)thsa0024 (author)
  • Das, PralayUmeå universitet,Kemiska institutionen (author)
  • Uvell, HannaUmeå universitet,Kemiska institutionen(Swepub:umu)hauv0001 (author)
  • Sinha, Arun KUmeå universitet,Kemiska institutionen (author)
  • Pinkner, Jerome SDepartment of Molecular Microbiology, Washington University, School of Medicine, St. Louis, Missouri 63110, USA (author)
  • Hultgren, Scott JDepartment of Molecular Microbiology, Washington University, School of Medicine, St. Louis, Missouri 63110, USA (author)
  • Almqvist, FredrikUmeå universitet,Kemiska institutionen(Swepub:umu)fral0001 (author)
  • Umeå universitetKemiska institutionen (creator_code:org_t)

Related titles

  • In:European Journal of Medicinal Chemistry: Elsevier Masson SAS46:4, s. 1103-11160223-52341768-3254

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