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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Solid-phase parallel synthesis of a tetrahydroindazolone library containing three unique core skeletons
Jonghoon Kim1, Heebum Song, Seung Bum Park
1Department of Chemistry, Seoul National University, 151-747 Seoul, South Korea.
Chemistry, an Asian Journal
|May 21, 2011
Summary
A novel solid-phase synthesis strategy efficiently created a diverse library of 1-(hetero)aryl-3-substituted tetrahydroindazolones. This method yields a 162-member library with high purity, suitable for drug discovery.
Area of Science:
- Medicinal Chemistry
- Organic Synthesis
- Drug Discovery
Background:
- Tetrahydroindazolones are a promising scaffold in medicinal chemistry.
- Efficient synthesis of diverse chemical libraries is crucial for drug discovery.
Purpose of the Study:
- To develop a regioselective synthesis for a 1-(hetero)aryl-3-substituted tetrahydroindazolone library.
- To maximize molecular diversity by incorporating varied core skeletons.
Main Methods:
- Solid-phase parallel synthesis utilizing in situ generated arylhydrazine.
- Condensation reactions with 2-acylcyclohexane-1,3-diones on solid supports.
- Introduction of nitrophenyl, anilyl, and pyridyl core skeletons.
Main Results:
- A library of 162 drug-like tetrahydroindazolones was constructed.
- High average purity of 92% was achieved without further purification.
- Diverse polar surface area and 3D chemical space were explored.
Conclusions:
- The developed strategy offers a practical and efficient route to tetrahydroindazolone libraries.
- The synthesized library exhibits significant molecular diversity for potential therapeutic applications.
- Solid-phase synthesis facilitates rapid library generation for screening.
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