title: Application of 6,7-indole aryne cycloaddition and Pd(0)-catalyzed Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions for the preparation of annulated indole libraries.
abstract: The construction of an unprecedented class of an indole-based library, namely, a 6,7-annulated-4-substituted 93-member indole library, using a strategic combination of 6,7-indolyne cycloaddition and cross-coupling reactions under both Suzuki-Miyaura and Buchwald-Hartwig conditions is described. This work represents the first example of library development that employs the indole aryne methodology. Annulated indoles, with the exception of only a few biologically active natural products (i.e., the trikentrins, herbindoles, teleocidins, and nodulisporic acids), have no representation in the PubChem or MLSMR databases. These structural entities are therefore predicted to have unique chemical property space characteristics and a high probability of exhibiting interesting biological activity.
authors.affiliation: Center of Excellence in Chemical Methodologies and Library Development, University of Kansas, Lawrence, 66047, United States.
authors.forename: Paul D
authors.initials: PD
authors.lastname: Thornton
authors.forename: Neil
authors.initials: N
authors.lastname: Brown
authors.forename: David
authors.initials: D
authors.lastname: Hill
authors.forename: Ben
authors.initials: B
authors.lastname: Neuenswander
authors.forename: Gerald H
authors.initials: GH
authors.lastname: Lushington
authors.forename: Conrad
authors.initials: C
authors.lastname: Santini
authors.forename: Keith R
authors.initials: KR
authors.lastname: Buszek
mesh_terms: D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007211:Indoles; D009942:Organometallic Compounds; D054852:Small Molecule Libraries; D010165:Palladium