Adenosine Deaminase Inhibitors: Synthesis and Biological Evaluation of Unsaturated, Aromatic, and Oxo Derivatives of (+)-erythro-9-(2‘S-Hydroxy-3‘R-nonyl)adenine [(+)-EHNA]
| Autor: | I. F. Chang, Vaibhav Varkhedkar, Mark A. Curtis, Palle V. P. Pragnacharyulu, Elie Abushanab |
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| Rok vydání: | 2000 |
| Předmět: |
Bicyclic molecule
biology Stereochemistry Chemistry Adenine Stereoisomerism Chemical synthesis Intestines Structure-Activity Relationship Adenosine deaminase Drug Discovery Adenosine Deaminase Inhibitors medicine biology.protein Animals Molecular Medicine Structure–activity relationship Cattle EHNA Enzyme Inhibitors Aliphatic compound Adenosine Deaminase Inhibitor medicine.drug |
| Zdroj: | Journal of Medicinal Chemistry. 43:4694-4700 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm0002533 |
| Popis: | The synthesis and biological evaluation of three classes of chain-modified derivatives of (+)-EHNA are described. Among the 5', 6'-unsaturated derivatives, the Z-isomer was the most potent inhibitor of adenosine deaminase (ADA) but 3-fold less active than (+)-EHNA. Several 9-aralkyladenines (ARADs) have been prepared, and their inhibitory activity was determined. A minimum of two carbon atoms separating the aromatic ring from the adenine-bearing carbon (C-3') was found to be essential for ADA activity equal to or slightly greater than that of (+)-EHNA. Finally, replacement of the C-5' carbon with an oxygen resulted in reduced potency. |
| Databáze: | OpenAIRE |
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