Synthesis of C-oxetanosyl-thiazole and its carbocyclic analog nucleosides as potential chemotherapeutic agents

Recent Advances on the Enantioselective Synthesis of C-Nucleosides Inhibitors of Inosine Monophosphate Dehydrogenase (IMPDH)

“…[33] Also 5'-, [25,34] 3'- [35] and 2'-substituted [36] derivatives have been reported but none showed significant biological activity. On the other hand, Popsavin and co-workers reported [37] Other sugar-analogues of tiazofurin including acyclic, [48] oxetane [49] and pyranosyl [50] derivatives have also been reported in the past but either low chemical yields were obtained in their synthesis or no significant biological activity was found.…”

Synthesis of Novel AZA-Analogues of Tiazofurin with 2-[5,5-bis(Hydroxymethyl)Pyrrolidin-2-yl] Framework as Sugar Mimic

“…The solvent was distilled off and the residue was purified by column chromatography (hexane/ethyl acetate, 3/1, v/v) to give 5 (1.93 g, 65%) as a colorless oil. δ H (CDCl 3 ) 4.11-4.05 (t-like m, 1H), 3 7, 98.3, 68.2, 68.0, 58.7, 46.7, 34.9, 30.1, 30.0, 27.3, 25.7, 22.7, 22.6. ν max (KBr) 3339, 2939(KBr) 3339, , 2861(KBr) 3339, , 1447(KBr) 3339, , 1368(KBr) 3339, , 1285(KBr) 3339, , 1158(KBr) 3339, , 1099(KBr) 3339, , 1038 Method B: The imine 4 (2.48 g, 11.8 mmol) was added to a stirred solution of HCN in DIPE (2M, 20 mL) at room temperature and stirring was continued overnight.…”

“…oxetane, [3] 1,3-dioxane, [4] 1,3-dioxolane, [5] isoxazolidine, [6] tetrahydrothiophene, [7] and pyrrolidine, [8] were reported. Among them, derivatives with pyrrolidine as the sugar mimic have been relatively little explored.…”