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Standard protecting groups create potent and selective κ opioids: Salvinorin B alkoxymethyl ethers

journal contribution
posted on 2008-02-01, 00:00 authored by Thomas Munro, K K Duncan, W Xu, Y Wang, L Y Liu-Chen, W A Carlezon, B M Cohen, C Béguin
Protection of salvinorin B as standard alkoxyalkyl ethers yielded highly potent κ opioid receptor agonists. Ethoxymethyl ether 6 is among the most potent and selective κ agonists reported to date. Fluoroethoxymethyl ether 11 is the first potent, selective fluorinated κ ligand, with potential use in MRI and PET studies. Further enlargement of the alkoxy group, alkylation of the acetal carbon, or heteroatom substitution all reduced activity. These protecting groups may prove useful in related work not only by enabling the use of harsher synthetic conditions, but potentially by optimizing the potency of the products. © 2007 Elsevier Ltd. All rights reserved.

History

Journal

Bioorganic and Medicinal Chemistry

Volume

16

Issue

3

Pagination

1279 - 1286

ISSN

0968-0896

Publication classification

CN.1 Other journal article