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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)
Author(s) -
Van Calenbergh Serge,
Van Den Eeckhout Elfride,
Herdewijn Piet,
De Bruyn André,
Verlinde Christophe,
Hol Wim,
Callens Mia,
Van Aerschot Arthur,
Rozenski Jef
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770306
Subject(s) - chemistry , glyceraldehyde 3 phosphate dehydrogenase , ribose , moiety , stereochemistry , dehydrogenase , thiophene , glyceraldehyde , adenosine , deoxyadenosine , ring (chemistry) , biochemistry , enzyme , organic chemistry
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)adenosine ( 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.