title: Chroman-4-one and chromone based somatostatin β-turn mimetics.
abstract: A scaffold approach has been used to develop somatostatin β-turn mimetics based on chroman-4-one and chromone ring systems. Such derivatives could adopt conformations resembling type II or type II' β-turns. Side chain equivalents of the crucial Trp8 and Lys9 in somatostatin were introduced in the 2- and 8-positions of the scaffolds using efficient reactions. Interestingly, this proof-of-concept study shows that 4 and 9 have Ki-values in the low μM range when evaluated for their affinity for the sst2 and sst4 receptors.
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Maria
authors.initials: M
authors.lastname: Fridén-Saxin
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Tina
authors.initials: T
authors.lastname: Seifert
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Marcus
authors.initials: M
authors.lastname: Malo
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Krystle
authors.initials: K
authors.lastname: da Silva Andersson
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Nils
authors.initials: N
authors.lastname: Pemberton
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Christine
authors.initials: C
authors.lastname: Dyrager
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Annika
authors.initials: A
authors.lastname: Friberg
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Kristian
authors.initials: K
authors.lastname: Dahlén
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden; Division of Pharmaceutical Chemistry and Technology, Faculty of Pharmacy, University of Helsinki, FIN-00014, Helsinki, Finland.
authors.forename: Erik A A
authors.initials: EA
authors.lastname: Wallén
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden.
authors.forename: Morten
authors.initials: M
authors.lastname: Grøtli
authors.affiliation: Department of Chemistry and Molecular Biology, Medicinal Chemistry, University of Gothenburg, SE-412 96, Göteborg, Sweden. Electronic address: luthman@chem.gu.se.
authors.forename: Kristina
authors.initials: K
authors.lastname: Luthman
mesh_terms: D040761:Biomimetic Materials / Q000737:chemistry / Q000494:pharmacology*; D002839:Chromans / Q000737:chemistry / Q000494:pharmacology*; D002867:Chromones / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D017481:Receptors, Somatostatin / Q000819:agonists*; D013004:Somatostatin / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D002839:Chromans; D002867:Chromones; D008024:Ligands; D017481:Receptors, Somatostatin; C574734:SSTR2 protein, human; C098681:somatostatin receptor subtype-4; D013004:Somatostatin
keywords: Chroman-4-one; Chromone; Peptidomimetics; Somatostatin