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From 1,4- to 1,5-Disubstituted Triazoles: Enhanced Three-Dimensionality and Aqueous Solubility.

Fumika Karaki1,2, Kei Ishii1, Kyoko Hidaka1

  • 1Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan.

Chemical & Pharmaceutical Bulletin
|March 29, 2026
PubMed
Summary

Replacing 1,4-disubstituted triazoles with 1,5-disubstituted triazoles in drug discovery enhances molecular shape and solubility. This strategy increases structural diversity for developing novel, 3D-shaped drug candidates.

Keywords:
1,5-disubstituted triazoleaqueous solubilitycopper-catalyzed azide–alkyne cycloadditiondruglikenessstructural diversitythree-dimensional library

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Drug Discovery

Background:

  • Copper-catalyzed azide-alkyne cycloaddition (CuAAC) yields 1,4-disubstituted triazoles, common in drug candidates but limited by rod-like shapes.
  • Existing drug compounds show a bias towards elongated shapes, potentially hindering optimal druglike properties.
  • Three-dimensional molecular structures generally exhibit more favorable druglike characteristics.

Purpose of the Study:

  • To investigate the replacement of 1,4-disubstituted triazoles with 1,5-disubstituted triazoles to improve molecular shape and diversity.
  • To assess the impact of this substitution on aqueous solubility and membrane permeability.
  • To develop a synthetic route for 1,5-disubstituted triazoles compatible with sterically hindered scaffolds.

Main Methods:

  • Construction of a new library of 7-azanorbornane-based compounds featuring 1,5-disubstituted triazole rings.
  • Attempted synthesis using Ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC), followed by an alternative acetylide-azide reaction.
  • Evaluation of synthesized compounds for molecular shape, aqueous solubility, and membrane permeability.

Main Results:

  • Ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) was unsuccessful for the designed sterically hindered compounds.
  • An alternative acetylide-azide reaction successfully yielded target 1,5-disubstituted triazoles, though not all designed molecules were obtained.
  • The 1,5-disubstituted triazoles exhibited increased three-dimensionality, greater structural diversity, and improved aqueous solubility compared to 1,4-disubstituted analogs.
  • No significant difference in membrane permeability was observed between the two types of triazoles.

Conclusions:

  • Replacing 1,4-disubstituted triazoles with 1,5-disubstituted counterparts is a viable strategy to enhance molecular shape and structural diversity.
  • This approach offers a promising route to develop drug candidate libraries with improved aqueous solubility.
  • The findings suggest a shift towards more three-dimensional scaffolds in medicinal chemistry for better druglike properties.