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; Yamato, Takehiko

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 (RNH 3+) of the guest. The structures of receptors cone-3 and cone-5 have been determined by X-ray crystallography. © 2012 The Royal Society of Chemistry.

Citation

Ni, X. L., Rahman, S., Wang, S., Jin, C. C., Zeng, X., Hughes, D. L., Redshaw, C., & Yamato, T. (2012). Hexahomotrioxacalix[3]arene derivatives as ionophores for molecular recognition of dopamine, serotonin and phenylethylamine. Organic & biomolecular chemistry, 10(23), 4618-4626. https://doi.org/10.1039/c2ob25177a

• Journal Article Type: Article
• Acceptance Date: Apr 17, 2012
• Online Publication Date: Apr 18, 2012
• Publication Date: Jun 21, 2012
• Deposit Date: Jun 8, 2022
• Journal: Organic and Biomolecular Chemistry
• Print ISSN: 1477-0520
• Publisher: Royal Society of Chemistry
• Peer Reviewed: Peer Reviewed
• Volume: 10
• Issue: 23
• Pages: 4618-4626
• DOI: https://doi.org/10.1039/c2ob25177a
• Public URL: https://hull-repository.worktribe.com/output/3622227