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Nitroreductase-triggered indazole formation.

Henrik Terholsen1, Lisa Medema1, Elizaveta Chernyshova1

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|February 2, 2026
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Enzymatic indazole synthesis is now possible using nitroreductase enzymes. This biocatalytic method efficiently converts nitrobenzylamine derivatives into valuable indazole compounds, advancing sustainable chemistry.

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Area of Science:

  • Biocatalysis
  • Organic Synthesis
  • Medicinal Chemistry

Background:

  • Biocatalysis offers sustainable synthetic routes but lacks enzymatic pathways for many compound classes, including indazoles.
  • Indazoles are important scaffolds in drug design, yet enzymatic synthesis routes remain underdeveloped.

Purpose of the Study:

  • To develop a novel enzymatic route for indazole formation using nitroreductase enzymes.
  • To explore the scope and limitations of this biocatalytic approach for synthesizing diverse indazole derivatives.

Main Methods:

  • Utilized two specific nitroreductase enzymes to catalyze the conversion of 2-nitrobenzylamine derivatives.
  • Investigated the formation of 1H- and 2H-indazoles based on N-substitution patterns.
  • Demonstrated the synthetic utility through a sequential cascade reaction with an imine reductase.

Main Results:

  • Achieved excellent conversions (up to >99%) of 2-nitrobenzylamine derivatives to indazoles.
  • Successfully synthesized 2H-indazoles from N-substituted intermediates and 1H-indazoles from other derivatives.
  • Demonstrated a scalable cascade reaction (50 mg scale) yielding up to 68% isolated product.

Conclusions:

  • Established a novel and efficient nitroreductase-triggered biocatalytic method for indazole synthesis.
  • The developed cascade reaction provides a sustainable route to 2H-indazoles from readily available starting materials.
  • This work expands the toolkit of enzymatic transformations for accessing valuable heterocyclic compounds in drug discovery.