1058142-07-6Relevant academic research and scientific papers
A β-fluoroamine inhibitor of purine nucleoside phosphorylase
Mason, Jennifer M.,Murkin, Andrew S.,Li, Lei,Schramm, Vern L.,Gainsford, Graeme J.,Skelton, Brian W.
, p. 5880 - 5884 (2008)
The potent immucillin purine nucleoside phosphorylase (PNP) inhibitors F-DADMe-ImmH [(3S,4S)-3], and [(3R,4R)-3] are synthesized in seven steps. Cycloaddition to a fluoroalkene and an enzymic resolution are the key features of the construction of the fluoropyrrolidines 11, from which the immucillins are assembled by use of a three-component Mannich reaction. Slow-onset binding constants (Ki*) for [(3S,4S)-3] and [(3R,4R)-3] with human PNP are 0.032 and 1.82 nM, respectively. F-DADMe-ImmH [(3S,4S)-3] exhibits oral availability in mice at doses as low as 0.2 mg/kg.
