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Synthesis and anti-tuberculosis activity of glycitylamines.

Authors :
Corkran HM
Dangerfield EM
Haslett GW
Stocker BL
Timmer MS
Source :
Bioorganic & medicinal chemistry [Bioorg Med Chem] 2016 Feb 15; Vol. 24 (4), pp. 693-702. Date of Electronic Publication: 2015 Dec 23.
Publication Year :
2016

Abstract

A series of glycitylamines, which were prepared in few steps from readily available carbohydrates, were tested for their ability to inhibit tuberculosis growth in an Alamar Blue BCG colourimetric assay. Several derivatives, including (2R,3R)-1-(hexadecylamine)pent-4-ene-2,3-diol, (2R,3R)-1-(hexadecylmethylamino)pent-4-ene-2,3-diol and 5-deoxy-5-hexadecylmethylamino-D-arabinitol, were prepared in good to excellent (44-90%) overall yield and exhibited micromolar (20-41μM) inhibitory activity that was similar to the first line tuberculosis (TB) drug ethambutol (39μM) in the same assay. The ease and low cost of the synthesis of the glycitylamines offers definite advantages for their use as potential TB drugs.<br /> (Copyright © 2016 Elsevier Ltd. All rights reserved.)

Details

Language :
English
ISSN :
1464-3391
Volume :
24
Issue :
4
Database :
MEDLINE
Journal :
Bioorganic & medicinal chemistry
Publication Type :
Academic Journal
Accession number :
26810833
Full Text :
https://doi.org/10.1016/j.bmc.2015.12.036