Synthesis of fluorinated purine and 1-deazapurine glycosides as potential inhibitors of adenosine deaminase |
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Authors: | Iaroshenko Viktor O Ostrovskyi Dmytro Petrosyan Andranik Mkrtchyan Satenik Villinger Alexander Langer Peter |
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Institution: | Institut fu?r Chemie der Universita?t Rostock, Albert-Einstein-Strasse 3a, D-18059 Rostock, Germany. viktor.iaroshenko@uni-rostock.de |
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Abstract: | The synthesis of 2- and 6-trifluoromethylated purines and 1-deazapurines was performed by formal 3 + 3]-cyclization reactions of 5-aminoimidazoles with a set of trifluoromethyl-substituted 1,3-CCC- and 1,3-CNC-dielectrophiles. The corresponding fluorinated nucleosides were synthesized by glycosylation of 9-unsubstituted purines and 1-deazapurines with peracetylated β-ribose, β-glucose, and rhamnose and subsequent deprotection. These scaffolds can be considered as potential inhibitors of adenosine deaminase (ADA) and inosine monophosphate dehydrogenase (IMPDH) enzymes. |
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