title: Hexahomotrioxacalix[3]arene derivatives as ionophores for molecular recognition of dopamine, serotonin and phenylethylamine.
abstract: The lower rim functionalized hexahomotrioxacalix[3]arene derivatives cone-3 and cone-5 bearing three benzyl and three N,N-diethyl-2-aminoethoxy groups, respectively, were synthesized from triol 1. Their complexation with 2-(3,4-dihydroxyphenyl)ethylamine (dopamine), 5-hydroxytryptamine (serotonin), and 2-phenylethylamine (phenethylamine), which have biologically important activities, has been studied by (1)H-NMR spectroscopy. The chemical shifts of the aromatic protons of the host and guest molecules and the up-field shifts of the ethyl protons of the guest molecules strongly suggest the formation of inclusion complexes in solution. The formation of the host-guest complexes is assisted by a hydrogen bond and/or an electrostatic interaction between the host and ammonium ion (RNH(3)(+)) of the guest. The structures of receptors cone-3 and cone-5 have been determined by X-ray crystallography.
authors.affiliation: Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi 1, Saga-shi, Saga 840-8502, Japan.
authors.forename: Xin-Long
authors.initials: XL
authors.lastname: Ni
authors.forename: Shofiur
authors.initials: S
authors.lastname: Rahman
authors.forename: Shi
authors.initials: S
authors.lastname: Wang
authors.forename: Cheng-Cheng
authors.initials: CC
authors.lastname: Jin
authors.forename: Xi
authors.initials: X
authors.lastname: Zeng
authors.forename: David L
authors.initials: DL
authors.lastname: Hughes
authors.forename: Carl
authors.initials: C
authors.lastname: Redshaw
authors.forename: Takehiko
authors.initials: T
authors.lastname: Yamato
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D004298:Dopamine / Q000737:chemistry*; D007476:Ionophores / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010627:Phenethylamines / Q000737:chemistry*; D012701:Serotonin / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D007476:Ionophores; D010627:Phenethylamines; C520695:hexahomotrioxacalix(3)arene; D047250:Calixarenes; C029261:phenethylamine; D012701:Serotonin; D004298:Dopamine