title: Synthesis and anti-tuberculosis activity of glycitylamines.
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.
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, 6140 Wellington, New Zealand; Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand.
authors.forename: Hilary M
authors.initials: HM
authors.lastname: Corkran
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, 6140 Wellington, New Zealand; Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand.
authors.forename: Emma M
authors.initials: EM
authors.lastname: Dangerfield
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, 6140 Wellington, New Zealand.
authors.forename: Gregory W
authors.initials: GW
authors.lastname: Haslett
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, 6140 Wellington, New Zealand; Malaghan Institute of Medical Research, PO Box 7060, Wellington, New Zealand. Electronic address: bridget.stocker@vuw.ac.nz.
authors.forename: Bridget L
authors.initials: BL
authors.lastname: Stocker
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, 6140 Wellington, New Zealand. Electronic address: mattie.timmer@vuw.ac.nz.
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D003124:Colorimetry; D004305:Dose-Response Relationship, Drug; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014376:Tuberculosis / Q000188:drug therapy*
chemical_list: D000588:Amines; D000995:Antitubercular Agents
keywords: Amines; Carbohydrates; Reductive amination; Synthesis; Tuberculosis