139757-70-3Relevant academic research and scientific papers
Selection of a synthetic glycan oligomer from a library of DNA-templated fragments against DC-SIGN and inhibition of HIV gp120 binding to dendritic cells
Ciobanu, Mihai,Huang, Kuo-Ting,Daguer, Jean-Pierre,Barluenga, Sofia,Chaloin, Olivier,Schaeffer, Evelyne,Mueller, Christopher G.,Mitchell, Daniel A.,Winssinger, Nicolas
, p. 9321 - 9323 (2011/10/09)
We report the synthesis of a nucleic acid-encoded carbohydrate library, its combinatorial self-assembly into 37485 pairs and a screen against DC-SIGN leading to the identification of consensus ligand motifs. A prototypical example from the selected pairs
Novel cyclic tetraselenides of mannose: synthesis and mechanistic studies
Sivapriya, Kirubakaran,Suguna, Perumal,Chandrasekaran, Srinivasan
, p. 2091 - 2095 (2008/02/04)
In this Letter, we disclose the synthesis of novel cyclic tetraselenides starting from mannose which are very unusual and rare and have been synthesised for the first time. The structures are confirmed by X-ray analysis. The reactivity of the reagent tetr
Asymmetric Synthesis and Biological Evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents
Jeong, Lak S.,Shinazi, Raymond F.,Beach, J. Warren,Kim, Hea O.,Nampalli, Satyanarayana,et al.
, p. 181 - 195 (2007/10/02)
In order to study the structure-acivity relationships of L-oxathiolanyl nucleosides as potential anti-HIV agents, a series of enantiomerically pure L-oxathiolanyl pyrimidine and purine nucleosides were synthesized and evaluated for anti-HIV-1 activity in human peripheral blood mononuclear (PBM) cells.The key intermediate 8 was synthesized starting from L-gulose via 1,6-thiaanhydro-L-gulopyranose.The acetate 8 was condensed with thymine, 5-substituted uracils and cytosines, 6-chloropurine, and 6-chloro-2-fluoropurine to give pyrimidine and purine nucleosides.Upon evaluation of these final nucleosides, the 5-fluorocytosine derivative 51 was found to be the most potent compound among those tested.In the case of 5-substituted cytosine analogues, the antiviral potency was found to be in the following decreasing order: cytosine (β-isomer) > 5-iodocytosine (β-isomer) > 5-fluorocytosine (α-isomer) > 5-methylcytosine (α-isomer) > 5-methylcytosine (β-isomer) > 5-bromocytosine (β-isomer) > 5-chlorocytosine (β-isomer).Among the thymine, uracil, and 5-substituted uracil derivatives, thymine (α-isomer) and uracil (β-isomer) derivatives exhibited moderate anti-HIV activity.In the purine series, the antiviral potency is found to be in the following decreasing order: adenine (β-isomer) > 6-chloropurine (β-isomer) > 6-chloropurine (α-isomer) > 2-NH2-6-Cl-purine (β-isomer) > guanine (β-isomer) > N6-methyladenine (α-isomer) > N6-methyladenine (β-isomer).The cytotoxicity was also determined in human PBM cells as well as Vero cells.None of the synthesized nucleosides was toxic up to 100 μ in PBM cells.
Structure-Activity Relationships of β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanyl Nucleosides as Potential Anti-HIV Agents
Jeong, Lak S.,Schinazi, Raymond F.,Beach, J. Warren,Kim, Hea O.,Shanmuganathan, Kirupathevy,et al.
, p. 2627 - 2638 (2007/10/02)
The β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanylpyrimidine and -purine nucleosides with natural nucleoside configuration were synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells.The key intermediate 14, which was uti
Enantiomeric Synthesis of (+)-BCH-189 cytosine> from D-Mannose and Its Anti-HIV Activity
Chu, Chung K.,Beach, J. Warren,Jeong, Lak S.,Choi, Bo G.,Comer, Frank I.,et al.
, p. 6503 - 6505 (2007/10/02)
Enantiomerically pure (+)-BCH-189 has been synthesized from D-mannose via 1,6-thioanhydro-D-mannose and its anti-HIV activity has been determined in peripheral blood mononuclear cells.
