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Multiple labeling of a potent CX 3 CR1 antagonist for the treatment of multiple sclerosis
Author(s) -
Malmquist Jonas,
Ström Peter
Publication year - 2012
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2958
Subject(s) - chemistry , isotopologue , antagonist , wittig reaction , aldehyde , chemical synthesis , strecker amino acid synthesis , specific activity , radiochemistry , medicinal chemistry , stereochemistry , nuclear chemistry , organic chemistry , biochemistry , in vitro , catalysis , enzyme , receptor , molecule , enantioselective synthesis
Several methods for the preparation of five isotopologues of the CX 3 CR1 antagonist 1 were developed. Volatile and radioactive 1‐chloro‐ and 1‐bromo‐ethyl‐benzene was handled in [2′‐ 14 C] and [3′, 5′‐ 3 H] labeling of 1. d ‐Leucinol (( R )‐2‐amino‐4‐methylpentan‐1‐ol) was labeled as [1‐ 14 C] and [4‐ 14 C] via a Wittig reaction using Garner's aldehyde and a Strecker amino acid synthesis with d ‐acylase resolvation, respectively. A [ 2 H 10 ] d ‐leucinol was used for the stable labeled [M + 10] isotopologue. The products were isolated with 97.6–100% stereo chemical and radiochemical purity as for specific activity 768 GBq/mmol and 1.6–2.0 GBq/mmol, respectively.