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Related Experiment Video

Updated: Jul 12, 2025

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
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Enabling, Decagram-Scale Synthesis of Macrocyclic MCL-1 Inhibitor ABBV-467.

Patrick B Brady1, Bryan K Sorensen1, Roberto M Risi1

  • 1Centralized Organic Synthesis Group, Small Molecule Therapeutic and Platform Technologies, AbbVie Inc., North Chicago, Illinois 60064, United States.

The Journal of Organic Chemistry
|November 1, 2023
PubMed
Summary

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This summary is machine-generated.

Researchers developed a scalable synthesis for ABBV-467, a potent MCL-1 inhibitor for multiple myeloma treatment. This decagram-scale synthesis enables crucial preclinical studies for this complex molecule.

Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Pharmacology

Background:

  • ABBV-467 is a potent and selective inhibitor of MCL-1, a protein implicated in multiple myeloma.
  • The clinical advancement of ABBV-467 necessitates a scalable synthetic route for preclinical evaluation.
  • The complex structure of ABBV-467 presents significant synthetic challenges.

Purpose of the Study:

  • To develop and describe a decagram-scale synthesis of ABBV-467.
  • To enable sufficient material for comprehensive preclinical characterization of ABBV-467.
  • To establish a robust and efficient synthetic strategy for a complex pharmaceutical target.

Main Methods:

  • Convergent and stereoselective synthetic strategy.
  • Key steps include hindered biaryl cross-coupling and enantioselective hydrogenation.

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  • Conformationally preorganized macrocyclization via C-O bond formation.

    • Main Results:

    • Successful decagram-scale synthesis of ABBV-467 achieved.
    • The developed route is convergent and stereoselective.
    • Key challenging steps were optimized for scalability.

    Conclusions:

    • A scalable synthetic route for ABBV-467 has been established.
    • This synthesis provides the necessary material for preclinical studies.
    • The strategy highlights efficient methods for constructing complex macrocyclic molecules.