Syntheses and Reactions of Bicyclic Heterocyclic Nucleosides and Nucleotides

Synthesis and Fluorescence Characterization of Pteridine Adenosine Nucleoside Analogs for DNA Incorporation

“…Step 1: Synthesis of 4-amino-6-methyl-7(8H)-pteridone (compound 3) (6). Two grams (16 mmol) of 4,5,6-triaminopyrimidine (compound 1) (7) and 2.2 ml of ethyl pyruvate (19 mmol) were heated under reflux in 20 ml of glacial acetic acid for 2 h. After cooling, the precipitate was collected, washed with water, and purified by recrystallization from 350 ml of a 1:1 (v/v) solution of dimethylformamide (DMF)/water.…”

Azidonucleosides: Synthesis, Reactions, and Biological Properties

“…The area of nucleoside modification has been reviewed extensively. [2][3][4][5][6][7][8][9][10] Specialized reviews on the synthesis of sugar-modified nucleosides, such as ketonucleosides, 11 3′-branched nucleoside analogues, 12 AIDS-driven nucleoside chemistry, 13 bicyclic heterocyclic nucleosides, 14 imidazole and benzimidazole nucleosides, 15 thio-and selenosugar-modified nucleosides, [16][17][18] nucleoside analogues with axial chirality, 19 C-nucleosides, 10,[20][21][22][23][24] isoxazolinyl-and isoxazolidinylnucleoside analogues, 25 acyclonucleosides, [26][27][28][29][30] Cbranched nucleoside analogues, 31 D-and L-enantiomers of the oxathiolane and dioxolane nucleosides, 32 carbocyclic nucleosides, [33][34][35][36] nucleosides with a sixmembered carbohydrate moiety, [37][38][39] nucleoside antibiotics, 40,41 azanucleosides, 42 boron-containing nucleosides, 43,44 L-nucleosides, 45,…”

“…Although the synthesis of modified nucleosides has been of interest for over four decades, the finding that 3‘-azido-3‘-deoxythymidine or AZT 1.001 is a therapeutic agent for the treatment of acquired immunodeficiency syndrome (AIDS) has triggered explosive new developments in the synthetic chemistry of nucleosides. The area of nucleoside modification has been reviewed extensively. − Specialized reviews on the synthesis of sugar-modified nucleosides, such as ketonucleosides, 3‘-branched nucleoside analogues, AIDS-driven nucleoside chemistry, bicyclic heterocyclic nucleosides, imidazole and benzimidazole nucleosides, thio- and selenosugar-modified nucleosides, − nucleoside analogues with axial chirality, C -nucleosides, ,− isoxazolinyl- and isoxazolidinylnucleoside analogues, acyclonucleosides, − C-branched nucleoside analogues, d - and l -enantiomers of the oxathiolane and dioxolane nucleosides, carbocyclic nucleosides, − nucleosides with a six-membered carbohydrate moiety, − nucleoside antibiotics, , azanucleosides, boron-containing nucleosides, , l -nucleosides, , 2‘,3‘-dideoxynucleosides, , 4‘,5‘-unsaturated nucleosides, C-alkenylation of pyrimidine nucleosides, anomeric spironucleosides, isonucleosides, nucleosides fluorinated in the sugar moiety, − …”