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A synthetic route to 9-(polyhydroxyalkyl)purines
Derek Horton1, Sheela Thomas, Judith Gallucci
1Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, DC 20016, USA. carbchm@american.edu
Carbohydrate Research
|July 11, 2006
Summary
Researchers synthesized novel acyclic nucleosides from 6-chloropurine and acetylated sugars. These compounds, including ribitol and arabinitol analogues, were modified via desulfurization and thiourea treatment, yielding potential therapeutic agents.
Area of Science:
- Organic Chemistry
- Nucleoside Chemistry
- Medicinal Chemistry
Background:
- Nucleoside analogues are crucial in antiviral and anticancer therapies.
- Developing novel synthetic routes to acyclic nucleosides is essential for drug discovery.
- 6-Chloropurine is a versatile building block for nucleoside synthesis.
Purpose of the Study:
- To synthesize novel acyclic nucleoside analogues of D-ribose and D-arabinose.
- To explore the chemical modifications of these nucleosides.
- To establish a synthetic pathway towards potential therapeutic agents.
Main Methods:
- Mercuric-ion promoted condensation of 6-chloropurine with acetylated sugar dithioacetals.
- Separation of diastereomers using chromatography.
- Desulfurization using tributylstannane.
- Conversion to thioxopurine analogues using thiourea.
- Deacetylation to yield final acyclic nucleosides.
Main Results:
- Successfully synthesized a mixture of diastereomeric acetylated acyclic nucleosides.
- Confirmed the structure of one diastereomer via X-ray crystallography.
- Achieved desulfurization to yield deoxy analogues.
- Converted deoxy analogues to 1,6-dihydro-6-thioxopurine derivatives.
- Obtained final deprotected acyclic nucleosides.
Conclusions:
- Established a new synthetic route for acyclic nucleosides.
- Demonstrated the utility of 6-chloropurine in synthesizing diverse nucleoside analogues.
- The synthesized compounds represent potential leads for further pharmacological investigation.