Abstract
The synthesis of glycosides and modified nucleosides represents a wide research field in organic chemistry. The classical methodology is based on coupling reactions between a glycosyl donor and an acceptor. An alternative strategy for new C-nucleosides is used in this approach, which consists of modifying a pre-existent furyl aglycone. This approach is applied to obtain novel pyridazine C-nucleosides starting with 2- and 3-(ribofuranosyl)furans. It is based on singlet oxygen [4+2] cycloaddition followed by reduction and hydrazine cyclization under neutral conditions. The mild three-step one-pot procedure leads stereoselectively to novel pyridazine C-nucleosides of pharmacological interest. The use of acetyls as protecting groups provides an elegant direct route to a deprotected new pyridazine C-nucleoside.
Highlights
IntroductionC-nucleosides represent a special moiety of this compound class due to their higher stability towards enzymatic and chemical hydrolysis than that of natural N-nucleosides, as well as owing to the interesting biological and pharmacological properties of some of their derivatives [1,2]
C-nucleoside isolated was pseudouridine [3], followed by showdomycin [4], and oxazinomycin [5]—all characterized by important pharmacological activities, from antitumor to antibacterial
We highlight that novel pyridazine C-nucleosides can be obtained starting with protected ribofuranosyl furans
Summary
C-nucleosides represent a special moiety of this compound class due to their higher stability towards enzymatic and chemical hydrolysis than that of natural N-nucleosides, as well as owing to the interesting biological and pharmacological properties of some of their derivatives [1,2]. C-nucleoside isolated was pseudouridine [3], followed by showdomycin [4], and oxazinomycin [5]—all characterized by important pharmacological activities, from antitumor to antibacterial. C-nucleosides comprise a sugar moiety and a non-natural heterocyclic base connected by a carbon–carbon bond. The stability of this bond and the broad structural variation in the heterocyclic base account for the high interest in this compound class [6,7,8,9]
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