Hexahomotrioxacalix[3]arene derivatives as ionophores for molecular recognition of dopamine, serotonin and phenylethylamine

Ni, Xin-Long, Rahman, Shofiur, Wang, Shi, Jin, Cheng-Cheng, Zeng, Xi, Hughes, David L., Redshaw, Carl and Yamato, Takehiko (2012) Hexahomotrioxacalix[3]arene derivatives as ionophores for molecular recognition of dopamine, serotonin and phenylethylamine. Organic & Biomolecular Chemistry, 10 (23). pp. 4618-4626. ISSN 1477-0520

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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 1H-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 (RNH3+) of the guest. The structures of receptors cone-3 and cone-5 have been determined by X-ray crystallography.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry
Depositing User:	Pure Connector
Date Deposited:	11 Jan 2016 17:00
Last Modified:	09 Nov 2022 10:31
URI:	https://ueaeprints.uea.ac.uk/id/eprint/56208
DOI:	10.1039/c2ob25177a

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