Adenosine deaminase inhibitors. Synthesis and biological evaluation of C1' and nor-C1' derivatives of (+)-erythro-9-[2(S)-hydroxy-3(R)-nonyl]adenine
| Autor: | Johanna D. Stoeckler, Geraldine C. B. Harriman, Rose Marie Midgett, Anne F. Poirot, Elie Abushanab |
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| Rok vydání: | 1992 |
| Předmět: |
Adenosine Deaminase
Stereochemistry Stereoisomerism In Vitro Techniques Amidine Structure-Activity Relationship chemistry.chemical_compound Adenosine deaminase Drug Discovery Adenosine Deaminase Inhibitors medicine Animals Structure–activity relationship Binding Sites biology Chemistry Adenine Diastereomer Biological activity biology.protein Molecular Medicine Cattle EHNA Adenosine Deaminase Inhibitor medicine.drug |
| Zdroj: | Journal of Medicinal Chemistry. 35:4180-4184 |
| ISSN: | 1520-4804 0022-2623 |
| DOI: | 10.1021/jm00100a025 |
| Popis: | The synthesis of various chiral derivatives of (+)-erythro-9-(2-hydroxy-3-nonyl)adenine, (+)-EHNA, from (2S,3R)-3-amino-1,2-O-isopropylidene-1,2-nonanediol by condensation with 5-amino-4,6-dichloropyrimidine is described. The compounds synthesized were C1'- and nor-C1'-(+)-EHNA derivatives. When tested with calf spleen ADA, C1'-OH- and nor-C1'-(+)-EHNA had comparable inhibitory activity that was 1 order of magnitude lower than that of (+)-EHNA. Potency was reduced further in nor-C1' derivatives. |
| Databáze: | OpenAIRE |
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