7-Substituted pyrrolo[2,3-d]pyrimidines for the synthesis of new 1-deazapyrimido[1,2,3-cd]purines

Muzychka, L. V.; Yaremchuk, I. O.; Смолий, О. Б.

doi:10.17721/fujcv5i2p15-23

Cited by 1 publication

(2 citation statements)

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“…The reduction of ketone to the hydroxy group resulted in alcohol 28 was performed with sodium borohydride in a methanol-water mixture. The authors also presented that protected 8,5′-(S)cyclo-2′,5′-dideoxyadenosine (28) could be transformed into mesylate 29, which underwent nucleophilic substitution after treatment with NaOH, leading to diastereomeric 8,5′-(R)cyclo-2′,5′-dideoxyadenosine (30). Similar transformations were also applied to pyrimidine nucleosides.…”

Section: The Synthesis Of Purine Cyclonucleosidesmentioning

confidence: 94%

“…Muzychka, during research on acyclic 7-deazapurine nucleoside analogues, observed the formation of cyclic salts resulting from the intramolecular attack of the halogen in the side chain on N3 atom of the 7-deazapurine ring [30,31] (Scheme 16). 7-Deazapurine 65, possessing an oxirane ring in the side chain, was heating in acetonitrile in the presence of triethylamine salts, which resulted in the opening of the oxirane ring and formation of intermediate 66 with subsequent intramolecular alkylation to inner salt 67.…”

Section: Scheme 13mentioning

confidence: 99%

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Synthesis and applications of cyclonucleosides: an update (2010–2023)

Burchiellaro,

Mieczkowski

2023

Mol Divers

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Cyclonucleosides are a group of nucleoside derivatives which, in addition to the classical N-glycosidic bond, have an additional covalent bond (linker, bridge) in their structure, which connects the heterocyclic base and sugar ring. The majority of them have been discovered in the laboratory; however, few such compounds have also been found in natural sources, including metabolites of sponges or radical damage occurring in nucleic acids. Due to their structural properties—rigid, fixed conformation—they have found wide applications in medicinal chemistry and biochemistry as biocides as well as enzyme inhibitors and molecular probes. They have also found use as convenient synthetic tools for the preparation of new nucleoside analogues, enabling structural modifications of both the sugar ring and heterocyclic base. This review summarizes the recent progress in the synthesis of various purine and pyrimidine cyclonucleosides using diverse chemical approaches based on radical, “click”, metal-mediated, and other types of reactions. It also presents recent reports concerning possible applications in medicinal chemistry, as well as their applications as valuable key intermediates in the synthesis of sugar- and base-modified nucleoside analogues and heterocyclic compounds. Graphical abstract

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Section: The Synthesis Of Purine Cyclonucleosidesmentioning

confidence: 94%

Section: Scheme 13mentioning

confidence: 99%