Synthesis of 2′-β-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors

Synthesis and evaluation of Janus type nucleosides as potential HCV NS5B polymerase inhibitors

“…The Vorbr ggen coupling reaction between 4-amino-6-bromo-5-cyanopyrrolo[2,3- d ]pyrimidine 6 11 and 1- O -acetyl-2,3,5-tri- O -benzoyl-β-D-ribofuranose 7a or 2’-β- C -methyl-1,2-di- O -benzoyl-3,5-di- O -toluyl-β-D-ribofuranose 7b 12 using N,O -bis(trimethylsilyl)acetamide (BSA) as the silylation agent and TMSOTf as the Lewis acid provided compounds 8a and 8b in 71% and 65% respectively. 13 Compounds 8a-b were then deprotected in saturated methanolic ammonia to give 9a-b . Subsequent halogen displacement with liquid ammonia in a steel bomb was followed by treatment with hydroxylamine 14 in ethanol which afforded compounds 11a-b in good yields.…”

Developments in Antiviral Drug Design, Discovery and Development in 2004

“…Valeant Pharmaceuticals disclose several derivatives that demonstrate EC 50 s below 10 µM in a replicon assay and possess good therapeutic indexes, although none were as active as the simple adenosine-based prototype 266 [787][788][789]. However, a marked increase in the cell-based activity of 267 was accomplished by synthesizing a prodrug of the monophosphate derivative, 268, which is over 150-fold more potent than the progenitor [787].…”

Synthesis and Structure Activity Relationship of Some Indole Derivatives as Potential Anti-inflammatory Agents

“…[46][47][48] Research in-dicated that α-amino ketones used for the preparation of o-amino-cyanopyrroles were usually obtained in situ [49][50][51] via the reaction of α-hydroxy ketones with amines in acid medium, [52][53][54][55] or via the reaction of α-halo ketones with either amines and/or α-amino acids. 56 As previously mentioned, α-hydroxy ketones and α-halo ketones, malononitriles or suitable substituted alkylidenemalonitrile and primary amines constituted essential components for the synthesis of o-amino-cyanopyrrole derivatives.…”