title: Solid-phase synthesis of methyl carboxymycobactin T 7 and analogues as potential antimycobacterial agents.
abstract: A solid-phase approach for the total synthesis of methyl carboxymycobactins 1a-d, with an on-resin cyclization leading to azopine 5 as the key step, was developed. The iron-affinity of these compounds was assessed by a competitive sulfoxine-binding assay, and antimycobacterial activity was tested against the growth of Mycobacterium avium.
authors.affiliation: MetaPhore Pharmaceuticals, Inc., 1910 Innerbelt Business Center Drive, Saint Louis, MO 63114, USA.
authors.forename: Amruta R
authors.initials: AR
authors.lastname: Poreddy
authors.forename: Otto F
authors.initials: OF
authors.lastname: Schall
authors.forename: Garland R
authors.initials: GR
authors.lastname: Marshall
authors.forename: Colin
authors.initials: C
authors.lastname: Ratledge
authors.forename: Urszula
authors.initials: U
authors.lastname: Slomczynska
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D007202:Indicators and Reagents; D007501:Iron / Q000737:chemistry; D007502:Iron Chelating Agents / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015269:Mycobacterium avium Complex / Q000187:drug effects* / Q000254:growth & development; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet
chemical_list: D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007502:Iron Chelating Agents; D010080:Oxazoles; C482468:methyl carboxymycobactin T 7; D007501:Iron