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Synthesis and Conformational Analysis of 2′-Deoxy-2′-(3-methoxybenzamido)adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH)

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Van Calenbergh, Serge Van Den Eeckhout, Elfride Herdewijn, Piet De Bruyn, André Verlinde, Christophe Van Aerschot, Arthur [UCL] Rozenski, Jef [UCL]

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.

Document type Article de périodique (Journal article) – Article de recherche
Publication date 1994
Language Anglais
Journal information "Helvetica Chimica Acta" - Vol. 77, no. 3, p. 631-644 (1994)
Peer reviewed yes
Publisher New Swiss Chemical Soc (Basel)
issn 0018-019X
e-issn 1522-2675
Publication status Publié
Affiliation UCL - (SLuc) Autre
Links
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Bibliographic reference Van Calenbergh, Serge ; Van Den Eeckhout, Elfride ; Herdewijn, Piet ; De Bruyn, André ; Verlinde, Christophe ; et. al. Synthesis and Conformational Analysis of 2′-Deoxy-2′-(3-methoxybenzamido)adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH). In: Helvetica Chimica Acta, Vol. 77, no. 3, p. 631-644 (1994)
Permanent URL http://hdl.handle.net/2078.1/48948