Synthesis and anti-tuberculosis activity of glycitylamines. Issue 4 (15th February 2016)

• Record Type: Journal Article
• Authors: Corkran, Hilary M.; Dangerfield, Emma M.; Haslett, Gregory W.; Stocker, Bridget L.; Timmer, Mattie S.M.
• Is Part Of: Bioorganic & medicinal chemistry. Volume 24:Issue 4(2016)
• Page Start: 693
• Page End: 702
• Publication Date: 2016-02-15
• Subjects: Tuberculosis -- Carbohydrates -- Amines -- Synthesis -- Reductive amination; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2015.12.036
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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 (20–41 μM) inhibitory activity that was similar to the first line tuberculosis (TB) drug ethambutol (39 μM) 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.