Design, synthesis and binding affinity of 3′-fluoro analogues of Cl-IB-MECA as adenosine A3 receptor ligands
| Autor: | Seung Jin Lee, Moo Hong Lim, Joong Hyup Kim, Neli Melman, Moon Woo Chun, Hea Ok Kim, Kenneth A. Jacobson, Lak Shin Jeong, Zhan Guo Gao, Hyung Ryong Moon |
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| Rok vydání: | 2003 |
| Předmět: |
Agonist
Adenosine Hydrocarbons Fluorinated medicine.drug_class Stereochemistry Clinical Biochemistry Pharmaceutical Science Carboxamide CHO Cells Ligands Biochemistry Chemical synthesis Radioligand Assay Structure-Activity Relationship chemistry.chemical_compound Cricetinae Drug Discovery Purinergic P1 Receptor Agonists medicine Animals Receptor Molecular Biology Hydrogen bond Receptor Adenosine A3 Organic Chemistry Receptors Purinergic P1 Adenosine A3 receptor Adenosine receptor Recombinant Proteins Rats Kinetics chemistry Drug Design Molecular Medicine Derivative (chemistry) Protein Binding |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 13:817-820 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/s0960-894x(03)00027-1 |
| Popis: | Several 3′-fluoro analogues, 1a , 1b , and 1c of selective and potent adenosine A 3 receptor agonist, Cl-IB-MECA were synthesized from d -xylose via highly regioselective opening of lyxo -epoxides, 8a and 8b with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A 3 adenosine receptor, the corresponding 3′-fluoro derivative showed remarkably decreased binding affinity, indicating that 3′-hydroxyl group acts as hydrogen bonding acceptor, not hydrogen bonding donor like fluorine atom in binding to the A 3 adenosine receptor. |
| Databáze: | OpenAIRE |
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