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[2]-Ladderanes as isosteres for meta-substituted aromatic rings and rigidified cyclohexanes

Author

Listed:
  • Rachel C. Epplin

    (Indiana University)

  • Shashwati Paul

    (Indiana University)

  • Loïc Herter

    (SpiroChem AG)

  • Christophe Salome

    (SpiroChem AG)

  • Erin N. Hancock

    (Indiana University
    Corteva Agriscience)

  • Jay F. Larrow

    (Novartis Institutes for BioMedical Research
    Relay Therapeutics)

  • Erich W. Baum

    (Novartis Institutes for BioMedical Research
    Relay Therapeutics)

  • David R. Dunstan

    (Novartis Institutes for BioMedical Research
    Relay Therapeutics)

  • Carol Ginsburg-Moraff

    (Novartis Institutes for BioMedical Research)

  • Thomas C. Fessard

    (SpiroChem AG)

  • M. Kevin Brown

    (Indiana University)

Abstract

Aromatic ring isosteres and rigidified saturated hydrocarbons are important motifs to enable drug discovery. Herein we disclose [2]-ladderanes as a class of meta-substituted aromatic ring isosteres and rigidified cyclohexanes. A straightforward synthesis of the building blocks is presented along with representative derivatization. Preliminary studies reveal that the [2]-ladderanes offer similar metabolic and physicochemical properties thus establishing this class of molecules as interesting motifs.

Suggested Citation

  • Rachel C. Epplin & Shashwati Paul & Loïc Herter & Christophe Salome & Erin N. Hancock & Jay F. Larrow & Erich W. Baum & David R. Dunstan & Carol Ginsburg-Moraff & Thomas C. Fessard & M. Kevin Brown, 2022. "[2]-Ladderanes as isosteres for meta-substituted aromatic rings and rigidified cyclohexanes," Nature Communications, Nature, vol. 13(1), pages 1-5, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-33827-3
    DOI: 10.1038/s41467-022-33827-3
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