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Title: Synthesis and conformational analysis of 2'-deoxy-2'-(3-methoxybenzamido)adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GADPH)
Authors: Vancalenbergh, Serge
Vandeneeckhout, E
Herdewijn, Piet
De Bruyn, André
Verlinde, C
Hol, W
Callens, M
Van Aerschot, Arthur
Rozenski, Jef #
Issue Date: 1994
Publisher: New swiss chemical soc
Series Title: Helvetica Chimica Acta vol:77 issue:3 pages:631-644
Abstract: A series of 2'-benzamido-2'-deoxyadenosine analogues were synthesized in an effort to find new lead structures for the treatment of sleeping sickness. The 2'-deoxy-2'-(3-methoxybenzamido)adenosin (1h) was proved to be a selective inhibitor of the parasite glyceraldehyde 3-phosphate dehydrogenase which confirms the modeling studies. The solution-state conformation of 2'-(thiophene-2-carboxamido) analogue 1d demonstrates a 2'-endo conformation, an orientation of the thiophene ring under the ribose moiety, and the base part occupying a 'syn'/'anti' equilibrium.
ISSN: 0018-019X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Medicinal Chemistry (Rega Institute)
# (joint) last author

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