Synthesis of symmetrical and non-symmetrical bivalent neurotransmitter ligands
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
A novel procedure for synthesis of bivalent neurotransmitter ligands was developed by reacting O-benzyl protected N-nosylated dopamine and serotonin with alkyl- or PEG-linked diols under Fukuyama-Mitsunobu conditions in the presence of DIAD/PPh3 generating three different bivalent neurotransmitter ligands in a one-pot reaction. The methodol. establishes a facile route towards bivalent neurotransmitter ligands, and libraries of in total 40 sym. and non-sym. bivalent and monovalent dopamine and serotonin compds. linked through alkyl or PEG spacers of varying length were prepd. Interestingly, attempted synthesis of an O-tert-Bu analog of the N-nosylated serotonin precursor resulted in unexpected tert-butylations at the 1-, 2- and 6-positions of the indole skeleton. We found that upscaling of selected bivalent serotonin ligands was most efficiently performed via N,O-bis-nosyl-serotonin since global de-nosylation was carried out as a final step after Fukuyama-Mitsunobu dimerization. [on SciFinder(R)]
Originalsprog | Engelsk |
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Tidsskrift | ChemistrySelect |
Vol/bind | 1 |
Udgave nummer | 3 |
Sider (fra-til) | 407-413 |
Antal sider | 7 |
ISSN | 2365-6549 |
DOI | |
Status | Udgivet - 2016 |
Bibliografisk note
M1 - Copyright (C) 2017 American Chemical Society (ACS). All Rights Reserved.
CAPLUS AN 2016:1614242(Journal; Online Computer File)
ID: 174370935