Synthesis of Novel Purinyl-1'-homocarbanucleosides Based on a Cyclopenta[b]pyrazine System

Influences of Phenyl Rings on NHC Ligands with Bicyclic Architectures

“…Other spectral data matched the reported data. 10 (4R,5S)-1,3-Dimethyl-4,5-(3S,5R-cyclopent-1-ene-3,5-diyl)imidazolinium Chloride (9). Imidazolidinone 8 was methylated in a 76% yield under the same reaction conditions as the synthesis of dimethylimidazolidine 4.…”

“…Data for the dimethylimidazolidinone S1: state: yellow oil; 1 H NMR (600 MHz, CDCl 3 , 299 K): δ = 6.01 (dd, J = 1.8, 1.8 Hz, 2H), 3.88 (dd, J = 1.8, 1.8 Hz, 2H), 3.14 (sep, J = 1.8 Hz, 2H), 2.71 (s, 6H), 1.62 (ddd, J = 9.6, 1.8, 1.8 Hz, 1H), 1.22 (d, J = 9.6 Hz, 1H) ppm; 13 (10). 9 Diacetylimidazolidinone 1 (360 mg, 1.54 mmol) was dissolved in a mixture of acetone/water (15 mL, 4:1) at 25 °C. N-Methylmorpholine N-oxide (4.8 M in H 2 O, 0.35 mL, 1.69 mmol) was added to this solution, followed by (after 5 min) an addition of a commercial solution of OsO 4 (0.02 mL, 2 wt % in water).…”

“…Other spectral data matched the reported data. 9 (3aR,4R,4aR,7aS,8S,8aS)-5,7-Diacetyl-2,2-dimethylperhydro-4,8methano [1,3]dioxolo[4,5-f ]benzoimidazol-6-one (11). 9 Acetone (33 mL) was added to a flask charged with exo-diol 10 (435 mg, 1.62 mmol) and a magnetic stir bar at 25 °C.…”

“…9 (3aR,4R,4aR,7aS,8S,8aS)-5,7-Diacetyl-2,2-dimethylperhydro-4,8methano [1,3]dioxolo[4,5-f ]benzoimidazol-6-one (11). 9 Acetone (33 mL) was added to a flask charged with exo-diol 10 (435 mg, 1.62 mmol) and a magnetic stir bar at 25 °C. p-Toluenesulfonic acid monohydrate (30.9 mg, 0.16 mmol) was added to the resultant solution, and the reaction mixture was heated at reflux for 1 h. The solution was concentrated under reduced pressure, and the crude residue was passed through a short pad of silica gel, eluted EtOAc, and concentrated under reduced pressure to afford the title compound 11 (486 mg, 97%) as a white solid.…”

Synthesis of New Indanyl Nucleoside Analogues and their Biological Evaluation on Hepatitis C Virus (HCV) Replicon

“…Taking into account our previous results [7,9], the literature available [17,18,19,20] regarding the activity observed for other indanyl nucleosides against different viruses, the fact that carbanucleosides derived from 2-amino-1-indanol have not been previously synthesized and evaluated as antiviral agents, and the persistent need to find effective new drugs for the treatment of hepatitis C, we decided to synthesize this type of derivative that contains triazole, purine, or azapurine moiety in their structures. Once synthesized, we evaluated their anti-HCV activity in vitro, by using the replicon cell line, Huh7.5 SG, to find new agents against this infection.…”