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Achieving Efficient Fragment Screening at XChem Facility at Diamond Light Source
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Accelerating fragment-based library generation by coupling high-performance photoreactors with benchtop analysis.

Quentin Lefebvre1, Christophe Salomé1, Thomas C Fessard1

  • 1SpiroChem AG, Rosental area, WRO-1047-3, Mattenstrasse 24, 4058 Basel, Switzerland.

Beilstein Journal of Organic Chemistry
|June 9, 2020
PubMed
Summary

A new workflow efficiently generates fragment libraries using photoredox-nickel dual-catalyzed N-arylation reactions. This method rapidly identifies privileged and challenging heterocyclic scaffolds for drug discovery.

Keywords:
N-arylationbenchtop analyticsfragment-based libraryheterocyclic sp2–sp3 fragmentsphotoredox-nickel dual catalysis

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Chemical Biology

Background:

  • Fragment-based drug discovery (FBDD) is a powerful approach for identifying novel drug leads.
  • Efficient synthesis of diverse fragment libraries is crucial for FBDD success.
  • Characterizing the reactivity of novel building blocks is essential for library design.

Purpose of the Study:

  • To develop an efficient workflow for generating fragment-based libraries.
  • To couple photoredox-nickel dual-catalyzed N-arylation reactions with benchtop analysis.
  • To rapidly assess the reactivity of spirocyclic and strained heterocyclic building blocks.

Main Methods:

  • Utilized a workflow coupling photoredox-nickel dual-catalyzed N-arylation reactions.
  • Employed advances in photoreactor design for reliable and reproducible experiments.
  • Investigated the reactivity of spirocyclic and strained heterocyclic scaffolds.

Main Results:

  • Successfully generated fragment-based libraries efficiently.
  • Gained rapid knowledge on the reactivity of various heterocyclic building blocks.
  • Identified privileged and challenging scaffolds for future drug discovery efforts.

Conclusions:

  • The developed workflow enables efficient library generation for FBDD.
  • The method provides rapid insights into the chemical space of heterocyclic scaffolds.
  • This approach accelerates the exploration of novel chemical matter in drug discovery.