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Related Experiment Videos

Multiple solid-phase synthesis of hydantoins and thiohydantoins

G Bhalay1, D Cowell, N D Hone

  • 1Oxford Diversity, Division of Oxford Asymmetry Ltd., Abingdon, Oxon, UK.

Molecular Diversity
|January 1, 1997
PubMed
Summary

A new method for creating hydantoins and thiohydantoins on a solid support was developed. This approach enabled the synthesis of a varied 96-compound library, advancing solid-phase synthesis techniques.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Hydantoins and thiohydantoins are important heterocyclic compounds with diverse biological activities.
  • Solid-phase synthesis offers advantages for library generation and purification.

Purpose of the Study:

  • To develop a novel general protocol for the solid-phase synthesis of hydantoins and thiohydantoins.
  • To demonstrate the utility of this method by synthesizing a diverse compound library.

Main Methods:

  • Development of a general solid-phase protocol for hydantoin and thiohydantoin construction.
  • Utilizing resin-bound dipeptides as starting materials.
  • Key step involves cyclization via in-situ formation of isocyanate or isothiocyanate intermediates on the resin.

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Main Results:

  • Successful establishment of a novel general protocol for solid-phase hydantoin and thiohydantoin synthesis.
  • Synthesis of a diverse 96-compound library using the developed methodology.
  • The strategy relies on the key step of cyclizing resin-bound dipeptides through isocyanate/isothiocyanate intermediates.

Conclusions:

  • The novel general protocol provides an efficient route for constructing hydantoin and thiohydantoin libraries on a solid support.
  • This methodology is versatile and applicable for generating diverse compound collections for drug discovery and chemical biology.
  • The key intermediate formation on resin is crucial for the success of the solid-phase synthesis.