title: Triazole-containing isothiazolidine 1,1-dioxide library synthesis: one-pot, multi-component protocols for small molecular probe discovery.
abstract: The construction of two libraries of triazole-containing isothiazolidine 1,1-dioxides is reported utilizing either a one-pot click/aza-Michael or click/OACC esterification protocol. One core dihydroisothiazole 1,1-dioxide scaffold was prepared rapidly on multigram scale via ring-closing metathesis (RCM) and was subjected to a one-pot multicomponent click/aza-Michael protocol with an array of amines and azides for the generation of a 180-member triazole-containing isothiazolidine 1,1-dioxide library. Alternatively, three daughter scaffolds were generated via the aza-Michael of three amino alcohols, followed by a one-pot, multicomponent click/esterification protocol utilizing a ring-opening metathesis polymerization (ROMP)-derived coupling reagent, oligomeric alkyl carbodiimide (OACC) to generate a 41-member library of triazole-containing isothiazole 1,1-dioxides.
authors.affiliation: Department of Chemistry, University of Kansas, Lawrence, 66045-7582, United States.
authors.forename: Alan
authors.initials: A
authors.lastname: Rolfe
authors.forename: Thomas O
authors.initials: TO
authors.lastname: Painter
authors.forename: Naeem
authors.initials: N
authors.lastname: Asad
authors.forename: Moon Young
authors.initials: MY
authors.lastname: Hur
authors.forename: Kyu Ok
authors.initials: KO
authors.lastname: Jeon
authors.forename: Marek
authors.initials: M
authors.lastname: Brzozowski
authors.forename: Sarra V
authors.initials: SV
authors.lastname: Klimberg
authors.forename: Patrick
authors.initials: P
authors.lastname: Porubsky
authors.forename: Benjamin
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: Paul R
authors.initials: PR
authors.lastname: Hanson
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003499:Cyclic S-Oxides / Q000138:chemical synthesis* / Q000737:chemistry; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015335:Molecular Probes / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D054852:Small Molecule Libraries / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D003499:Cyclic S-Oxides; D007555:Isoxazoles; D015335:Molecular Probes; D054852:Small Molecule Libraries; D014230:Triazoles