title: Multi-component assembly of the bicyclic core associated with the tRNA synthetase inhibitors SB-203207 and SB-203208. Application to the synthesis of biologically active analogues.
abstract: The ketone (+/-)-5, which embodies the bicyclic core associated with the title tRNA synthetase inhibitors 1 and 2, has been prepared via a three-component coupling reaction involving 2-(hydroxymethyl)cyclopent-2-enone (15), methylamine (6) and propiolamide (10); straightforward elaboration of the readily derived acetates (-)-21 and (+)-21 has provided the biologically active analogues 23 and 24, respectively, of the title compounds.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia. mgb@rsc.anu.edu.au
authors.forename: M G
authors.initials: MG
authors.lastname: Banwell
authors.forename: C F
authors.initials: CF
authors.lastname: Crasto
authors.forename: C J
authors.initials: CJ
authors.lastname: Easton
authors.forename: T
authors.initials: T
authors.lastname: Karoli
authors.forename: D R
authors.initials: DR
authors.lastname: March
authors.forename: M R
authors.initials: MR
authors.lastname: Nairn
authors.forename: P J
authors.initials: PJ
authors.lastname: O'Hanlon
authors.forename: M D
authors.initials: MD
authors.lastname: Oldham
authors.forename: A C
authors.initials: AC
authors.lastname: Willis
authors.forename: W
authors.initials: W
authors.lastname: Yue
mesh_terms: D000604:Amino Acyl-tRNA Synthetases / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000494:pharmacology; D007192:Indenes / Q000737:chemistry* / Q000494:pharmacology; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D007192:Indenes; C410786:SB 203207; C410787:SB 203208; D013449:Sulfonamides; D000604:Amino Acyl-tRNA Synthetases