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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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5,5- and 5,6-Membered Spirocyclic Indolinone Hit-Finding Libraries.

Peter Meier1, Nicole Battaglia1, Peter Ertl1

  • 1Global Discovery Chemistry , Novartis Institutes for Biomedical Research , CH-4056 Basel , Switzerland.

ACS Combinatorial Science
|June 28, 2019
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Summary

Two novel spirocyclic indolinone libraries were created using a rigorous evaluation process. These diverse compound collections expand chemical space complementary to existing databases.

Keywords:
combinatorial chemistryhit finding librariesspirocyclic compounds

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Area of Science:

  • Medicinal Chemistry
  • Drug Discovery
  • Organic Synthesis

Background:

  • Spirocyclic indolinones are privileged scaffolds in medicinal chemistry.
  • Developing diverse compound libraries is crucial for identifying novel drug candidates.
  • Systematic library design requires robust evaluation procedures.

Purpose of the Study:

  • To describe the production of two spirocyclic indolinone libraries.
  • To select scaffolds using a computational and experimental evaluation procedure.
  • To assess the novelty and diversity of the produced libraries.

Main Methods:

  • Scaffold selection based on computed physicochemical properties and prototype compound data.
  • Library production yielding 176 and 428 compounds from two related scaffolds.
  • Novelty and diversity analysis against the PubChem database.

Main Results:

  • Successful isolation of 176 and 428 spirocyclic indolinone compounds with high purity.
  • Demonstration of complementarity to the PubChem chemical space.
  • Validation of the library evaluation procedure for scaffold selection.

Conclusions:

  • The described method efficiently generates diverse and novel spirocyclic indolinone libraries.
  • These libraries represent valuable resources for drug discovery programs.
  • The findings highlight the utility of integrated computational and experimental approaches in library design.