title: Beyond the Diketopiperazine Family with Alternatively Bridged Brevianamide F Analogues.
abstract: A method for the preparation of 3,5-bridged piperazin-2-ones from a tryptophan-proline-based diketopiperazine is described using diphosgene to induce the ring closure. Density functional theory calculations were conducted to study the mechanism of this C-C bond formation. Several derivatives of the thus obtained α-chloroamine were synthesized by substitution of the chlorine atom using a range of O-, N-, S-, and C-nucleophiles. This novel class of brevianamide F analogues possess interesting breast cancer resistance protein inhibitory activity.
authors.affiliation: †Research Group SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
authors.forename: I
authors.initials: I
authors.lastname: Wauters
authors.affiliation: ‡Center for Molecular Modelling, Ghent University, Technologiepark 903, 9000 Ghent, Belgium.
authors.forename: H
authors.initials: H
authors.lastname: Goossens
authors.affiliation: †Research Group SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
authors.forename: E
authors.initials: E
authors.lastname: Delbeke
authors.affiliation: †Research Group SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
authors.forename: K
authors.initials: K
authors.lastname: Muylaert
authors.affiliation: †Research Group SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
authors.forename: B I
authors.initials: BI
authors.lastname: Roman
authors.affiliation: §XStruct, Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281, S3, 9000 Ghent, Belgium.
authors.forename: K
authors.initials: K
authors.lastname: Van Hecke
authors.affiliation: ‡Center for Molecular Modelling, Ghent University, Technologiepark 903, 9000 Ghent, Belgium.
authors.forename: V
authors.initials: V
authors.lastname: Van Speybroeck
authors.affiliation: †Research Group SynBioC, Department of Sustainable Organic Chemistry and Technology, Ghent University, Coupure Links 653, 9000 Ghent, Belgium.
authors.forename: C V
authors.initials: CV
authors.lastname: Stevens
mesh_terms: D001943:Breast Neoplasms / Q000737:chemistry / Q000188:drug therapy*; D054659:Diketopiperazines / Q000737:chemistry*; D005260:Female; D006801:Humans; D026121:Indole Alkaloids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008958:Models, Molecular; D008968:Molecular Conformation; D009363:Neoplasm Proteins / Q000037:antagonists & inhibitors*; D011789:Quantum Theory; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D054659:Diketopiperazines; D026121:Indole Alkaloids; D009363:Neoplasm Proteins; C000590722:brevianamide F