Solid-phase synthesis of methyl carboxymycobactin T 7 and analogues as potential antimycobacterial agents.
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.
Poreddy
Amruta R
AR
MetaPhore Pharmaceuticals, Inc., 1910 Innerbelt Business Center Drive, Saint Louis, MO 63114, USA.
Schall
Otto F
OF
Marshall
Garland R
GR
Ratledge
Colin
C
Slomczynska
Urszula
U
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
D000900:Anti-Bacterial Agents; D007202:Indicators and Reagents; D007502:Iron Chelating Agents; D010080:Oxazoles; C482468:methyl carboxymycobactin T 7; D007501:Iron