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Syntheses of highly functionalised 6-substituted pteridines
Donie Guiney1, Colin L Gibson, Colin J Suckling
1Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland, UK G1 1XL.
Organic & Biomolecular Chemistry
|August 22, 2003
Summary
New Wittig reaction methods enable the synthesis of diverse 6-substituted pteridines. These compounds are valuable for developing modulators of tetrahydrobiopterin activity and dihydroneopterin aldolase inhibitors.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Synthetic Chemistry
Background:
- Pteridine derivatives are crucial in biological processes.
- Developing novel synthetic routes for functionalized pteridines is essential for drug discovery.
Purpose of the Study:
- To describe improved methods for synthesizing polyfunctional 6-substituted pteridines.
- To explore the introduction of various functional groups via Wittig reactions.
Main Methods:
- Utilized improved Wittig reaction methodologies with 2-thioalkyl-6-formylpteridines as substrates.
- Introduced alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy, and dihydroxy groups.
- Employed ligand-assisted osmium tetraoxide catalysis for selective vic-diol formation from alkenes.
Main Results:
- Successfully synthesized a range of polyfunctional 6-substituted pteridines.
- Demonstrated the versatility of the Wittig reaction for pteridine functionalization.
- Achieved selective dihydroxylation of derived alkenes.
Conclusions:
- The developed methods provide efficient access to diverse pteridine scaffolds.
- These compounds hold potential as modulators of tetrahydrobiopterin activity.
- The synthesized pteridines may serve as inhibitors of dihydroneopterin aldolase.