149712-92-5Relevant academic research and scientific papers
Stereoselective synthesis of rac-4′-ethynyl-2′-deoxy- and 4′-ethynyl-2′,3′-dideoxy-2′,3′- didehydronucleoside analogues
Maddaford, Adrian,Wainwright, Philip,Glen, Rebecca,Fisher, Ray,Dragovich, Peter S.,Gonzalez, Javier,Kung, Pei-Pei,Middleton, Donald S.,Pryde, David C.,Stephenson, Peter S.,Sutton, Scott C.
, p. 1378 - 1384 (2007)
Synthesis of a racemic 4′-ethynyl-2′-deoxyribose intermediate using stereoselective chelation control is presented. This intermediate is further transformed to 4′-ethynyl-2′-deoxy- and 4′-ethynyl- 2′,3′-dideoxy-2′,3′-didehydronucleoside analogues. Georg T
Synthesis and biological evaluation of l- and d-configurations of 2′,3′-dideoxy-4′-c-methyl-3′-oxacytidine analogues
Liu, Mao-Chin,Luo, Mei-Zhen,Mozdziesz, Diane E.,Lin, Tai-Shun,Dutschman, Ginger E.,Gullen, Elizabeth A.,Cheng, Yung-Chi,Sartorelli, Alan C.
, p. 2301 - 2304 (2007/10/03)
Novel L- and D-configuration 2′,3′-dideoxy-4′-C-methyl-3′-oxacytidine and their 5-fluoro analogues have been synthesized from 1-benzyloxy-2-propanone and L-ascorbic acid in eight steps and evaluated for biological activity.
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
