Abstract
On the basis of high binding affinity of 3′-aminoadenosine derivatives 2b at the human A3 adenosine receptor (AR), 3′- acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O- isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A3AR, our results revealed that 3′-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A3AR.
Original language | English |
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Pages (from-to) | 408-420 |
Number of pages | 13 |
Journal | Nucleosides, Nucleotides and Nucleic Acids |
Volume | 27 |
Issue number | 4 |
DOIs | |
State | Published - Apr 2008 |
Keywords
- 3′-acetamidoadenosines
- Human A adenosine receptor
- Hydroboration-oxidation
- Hydrogen bonding donor
- Steric effects