190078-48-9Relevant academic research and scientific papers
Stereoselective synthesis of β-L-2',3'- dideoxy- and L-2',3'- didehydro-2',3'-dideoxy purine nucleosides
Wang, Peiyuan,Bolon, Pascal J.,Newton, M. Gary,Chua, Chung K.
, p. 2819 - 2835 (2007/10/03)
β-L-2',3'-Dideoxy- and L-2',Y-didehydro-2',Y-dideoxy purine nucleosides have been synthesized via a highly stereoselective method of glycosylation by the condensation of L-2-(phenylselenyl)-2,3-dideoxyribose derivative with silylated heterocyclic base.
Synthesis and biological properties of the four optical isomers of 5-o- carboranyl-2',3'-didehydro-2',3'-dideoxyuridine
Graciet, Jean-Christophe G.,Shi, Junxing,Schinazi, Raymond F.
, p. 711 - 727 (2007/10/03)
The four isomers of the 5-o-carboranyl-2',3'-didehydro-2',3'- dideoxyuridine (d4CU) were synthesized and their antiviral activity and cytotoxicity in normal and cancer human cells determined. Coupling of silylated 5-o-carboranyluracil with the protected D/L 2,3-dideoxy-2- phenylselenenylribosylacetates provided after oxidative elimination and deprotection, the desired compounds. The presence of the electron deficient 5-o-carboranyl moiety on uracil influenced the yield of the various isomers. In general, the compounds demonstrated weak anti-human immunodeficiency virus activity in primary human lymphocytes. No marked difference in the biological profile was noted for the various optical isomers, suggesting that the high lipophilicity of these nucleosides imparted by the carboranyl moiety overrides stereochemical considerations in the 2',3'-didehydro-2',3'- dideoxyaglycon moiety.
Stereoselective syntheses of β-L-FD4C and β-L-FddC
Chen, Shu-Hui,Li, Xiuyan,Li, Jun,Niu, Chuansheng,Carmichael, Ellen,Doyle, Terrence W.
, p. 3449 - 3452 (2007/10/03)
Stereocontrolled syntheses of two potent antiviral agents, β-L-FD4C and β-L-FddC, were accomplished both in 10-step sequences, with an overall yield of 27% and 25%, respectively. It is worthwhile to mention that the introduction of a phenylseleno moiety to the C-2α position of the lactone 4 can now be performed in a stereocontrolled fashion, providing the key intermediate 5α in 75% yield.
Anti-human immunodeficiency and anti-hepatitis B virus activities of β-L-2',3'-dideoxy purine nucleosides
Bolon, Pascal J.,Wang, Peiyuan,Chu, Chung K.,Gosselin, Gilles,Boudou, Valerie,Pierra, Claire,Mathe, Christophe,Imbach, Jean-Louis,Faraj, Abdesselem,El Alaoui, M. Abdelaziz,Sommadossi, Jean-Pierre,Balakrishna Pai,Zhu, Yong-Lian,Lin, Ju-Sheng,Cheng, Yung-Chi,Schinazi, Raymond F.
, p. 1657 - 1662 (2007/10/03)
β-L-2',3'-Dideoxyadenosine, β-L-2',3'-didehydro-2',3'-dideoxyadenosine and related compounds were synthesized in a stereoselective manner. These compounds were tested in vitro against HBV in 2.2.15 cell line and against HIV-1 in PBM and CEM cells. It was found that β-L-2',3'-didehydro-2',3'-dideoxyadenosine (7) exhibited significant anti-HIV (EC50 0.38 μM in PBM cells) and anti-HBV activity (EC50 1.2 μM).
