1. Synthesis and anti-tuberculosis activity of glycitylamines.
- Author
-
Corkran HM, Dangerfield EM, Haslett GW, Stocker BL, and Timmer MS
- Subjects
- Amines chemical synthesis, Amines chemistry, Antitubercular Agents chemical synthesis, Antitubercular Agents chemistry, Colorimetry, Dose-Response Relationship, Drug, Microbial Sensitivity Tests, Molecular Structure, Structure-Activity Relationship, Amines pharmacology, Antitubercular Agents pharmacology, Mycobacterium tuberculosis drug effects, Tuberculosis drug therapy
- 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., (Copyright © 2016 Elsevier Ltd. All rights reserved.)
- Published
- 2016
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