title: Chemical conversion of nocathiacin I to nocathiacin II and a lactone analogue of glycothiohexide alpha.
abstract: Nocathiacin I (1) was converted to its deoxy indole analogue, nocathiacin II (2), another natural product, by a unique and facile chemical process. This process was applied to nocathiacin IV (4), generating the lactone analogue of glycothiohexide alpha (5), which was also prepared from nocathiacin II by a mild hydrolytic process. In contrast to glycothiohexide alpha (3), this lactone analogue (5) was found to exhibit in vivo antibacterial efficacy in an animal (mouse) infection model.
authors.affiliation: Pharmaceutical Research Institute, Bristol-Myers Squibb Company, 5 Research Parkway, Wallingford, Connecticut 06492, USA.
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Connolly
authors.forename: Alicia
authors.initials: A
authors.lastname: Regueiro-Ren
authors.forename: John E
authors.initials: JE
authors.lastname: Leet
authors.forename: Dane M
authors.initials: DM
authors.lastname: Springer
authors.forename: Jason
authors.initials: J
authors.lastname: Goodrich
authors.forename: Xiaohua Stella
authors.initials: XS
authors.lastname: Huang
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Pucci
authors.forename: Junius M
authors.initials: JM
authors.lastname: Clark
authors.forename: Joanne J
authors.initials: JJ
authors.lastname: Bronson
authors.forename: Yasutsugu
authors.initials: Y
authors.lastname: Ueda
mesh_terms: D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D004195:Disease Models, Animal; D036341:Intercellular Signaling Peptides and Proteins; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010455:Peptides / Q000737:chemistry* / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000494:pharmacology; D013844:Thiazoles / Q000737:chemistry / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D036341:Intercellular Signaling Peptides and Proteins; D010455:Peptides; D010456:Peptides, Cyclic; D013844:Thiazoles; C089609:glycothiohexide alpha; C463319:nocathiacin I; C500764:nocathiacin II; C473548:nocathiacin IV