Coupling of 2,6-dichloropurine and 2,6-dichlorodeazapurines with ribose and ribose modified sugars
Substituted purine and deazapurine nucleosides are of great interest in medicinal chemistry. Furthermore, 3'-deoxynucleosides exhibit a number of biological activities. In this research the coupling of 2,6-dichloro-1- or 3- deazapurine with protected 3'-d
Synthesis and adenosine deaminase inhibitory activity of 3'-deoxy-1- deazaadenosines
New 1-deazapurine nuclcosides were synthesized by coupling 2,6-dichloro- 1-deaza-9H-purine (= 5,7-dichloro-3H-imidazo[4,5-b]pyridine) with a 3- deoxyribose derivative by the acid-catalyzed fusion method. The condensation reaction gave an anomeric mixture
3'-deoxyribofuranose derivatives of 1-deaza and 3-deaza-adenosine and their activity as adenosine deaminase inhibitors.
2,6-Dichloro-1-deazapurine and 2,6-dichloro-3-deazapurine were coupled with 1,2-O-diacetyl-5-O-benzoyl-3-deoxy-beta-D-ribofuranose. Deprotection of the obtained compounds and reaction with liquid ammonia gave the desired 2-chloroadenine nucleosides, which were dechlorinated to afford the corresponding 1-deaza and 3-deazaadenosine derivatives. Biological studies performed on ADA from calf intestine showed that these new nucleosides are inhibitors of the enzyme.