188744-83-4Relevant academic research and scientific papers
Transition state analogue inhibitors of protozoan nucleoside hydrolases
Furneaux, Richard H.,Schramm, Vern L.,Tyler, Peter C.
, p. 2599 - 2606 (2007/10/03)
Protozoan parasites are unable to synthesize purines de novo and must rely on purine salvage pathways for their requirements. Nucleoside hydrolases, which are not found in mammals, function as key enzymes in purine salvage in protozoa. Inhibition of these enzymes may disrupt purine supply and specific inhibitors are potential therapeutic agents for the control of protozoan infections. A series of 1,4-dideoxy-1,4-imino-D-ribitols bearing C- bonded aromatic substituents at C-1 have been synthesized, following carbanion additions to the imine 2, and tested as potential nucleoside hydrolase inhibitors. Nucleoside analogues 8, 11, 14, 17, 20, 24-26, 28 exhibit K(i) values in the range 0.2-22 μM against two representative isozymes of protozoan nucleoside hydrolases. (C) 1999 Elsevier Science Ltd.
Synthesis of transition state inhibitors for N-riboside hydrolases and transferases
Furneaux, Richard H.,Limberg, Gerrit,Tyler, Peter C.,Schramm, Vern L.
, p. 2915 - 2930 (2007/10/03)
A number of 1,4-dideoxy-1,4-imino-1-(S)-(substituted phenyl)-D-ribitols bearing aromatic OH, NH2, NO2, CO2H and halogeno moieties, and a 3-pyridyl analogue have been synthesized. The key step is die condensation of aryllithium or aryl Grignard reagents with the imine 3; derived from the protected 1,4-dideoxy-1,4-imino-D-ribitol 4.
