Synthesis and structure-activity relationships of adenosine analogs as inhibitors of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. Modifications at positions 5' and 8

A M Aronov; M H Gelb

doi:10.1016/s0960-894x(98)00635-0

Synthesis and structure-activity relationships of adenosine analogs as inhibitors of trypanosomal glyceraldehyde-3-phosphate dehydrogenase. Modifications at positions 5' and 8

Bioorg Med Chem Lett. 1998 Dec 15;8(24):3505-10. doi: 10.1016/s0960-894x(98)00635-0.

Authors

A M Aronov¹, M H Gelb

Affiliation

¹ Department of Chemistry, University of Washington, Seattle 98195, USA.

PMID: 9934461
DOI: 10.1016/s0960-894x(98)00635-0

Abstract

A number of 5', N6- and C8, N6-disubstituted adenosine analogs was synthesized and tested for inhibition of trypanosomal glyceraldehyde 3-phosphate dehydrogenase. The most active compound, N6-(3-methyl-2-butenyl)-8-(2-thienyl)adenosine, had Kl of 9 microM and was marginally selective for the parasite enzyme.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Adenosine / analogs & derivatives*
Adenosine / chemical synthesis
Adenosine / pharmacology
Animals
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Enzyme Inhibitors / pharmacology
Glyceraldehyde-3-Phosphate Dehydrogenases / antagonists & inhibitors*
Leishmania mexicana / enzymology
Magnetic Resonance Spectroscopy
Molecular Structure
Structure-Activity Relationship
Trypanosoma / enzymology*

Substances

Enzyme Inhibitors
Glyceraldehyde-3-Phosphate Dehydrogenases
Adenosine