194783-33-0Relevant academic research and scientific papers
HYDROXYLATED ERYTHRO-HYDROXYNONYL ADENINES AND RELATED ANALOGS
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, (2008/06/13)
This invention discloses various analogs of erythro-hydroxynonyladenine (EHNA) which have been modified by the addition of hydroxy groups or other moieties at the #8 or #9 carbon atoms of the side-chain portion of the molecule (i.e., the erythro-hydroxynonyl chain which is attached to the adenosine ring structure). It also discloses synthetic reagents and steps that can be used to create these and other analogs of EHNA which contain hydroxyl, halide, acid, ester, ether, amine, azide, or other moieties at such locations, or at other controllable locations such as the #5, #6, or #7 carbon atoms on the side-chain. Analogs containing such side-chain modifications can also be modified in the adenosine structure if desired. The hydroxylated analogs described herein have been shown to inhibit adenosine deaminase (ADA) at therapeutically useful levels. The relevant Ki values are in the range of 10-8 to 10-9, which is within a desired range of about 10-7 to about 10-10. EHNA analogs that have potencies within this range can effectively inhibit ADA activity on a reversible basis, without permanently poisoning the enzyme. It has also been discovered that some of these analogs have an additional therapeutic value when used to protect heart muscle against ischemic damage
Adenosine Deaminase Inhibitors. Synthesis and Biological Evaluation of Putative Metabolites of (+)-erythro-9-(2S-Hydroxy-3R-nonyl)adenine
Vargeese, Chandra,Sarma, Mallela S. P.,Pragnacharyulu, Palle V. P.,Abushanab, Elie,Li, Shih-Ying,Stoeckler, Johanna D.
, p. 3844 - 3849 (2007/10/02)
The synthesis and biological evaluation of three chain-hydroxylated (+)-erythro-9-(2S-hydroxy-3R-nonyl)adenine derivatives are reported.Hydroxy groups at positions 9',8', and 8',9'(12,25, and 16) were introduced by either epoxidation or hydrobo
