Synthesis and Conformational Analysis of 2′-Deoxy-2′-(3-methoxybenzamido)adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH)
(1994) Helvetica Chimica Acta — Vol. 77, n° 3, p. 631-644 (1994)
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- 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.
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Van Calenbergh, S., Van Den Eeckhout, E., Herdewijn, P., De Bruyn, A., Verlinde, C., Hol, W., Callens, M., Van Aerschot, A., & Rozenski, J. (1994). Synthesis and Conformational Analysis of 2′-Deoxy-2′-(3-methoxybenzamido)adenosine, a rational-designed inhibitor of trypanosomal glyceraldehyde phosphate dehydrogenase (GAPDH). Helvetica Chimica Acta, 77(3), 631-644. https://doi.org/10.1002/hlca.19940770306 (Original work published 1994)