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Synthesis of [ 14 C]‐labelled eicosa‐5,8,11‐triynoic acid and conversion to anti‐inflammatory amides
Author(s) -
Pilgrim W. R.,
Nedoncelle P.,
Shroot B.,
Maignan J.,
Restlé S.
Publication year - 1991
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.2580290706
Subject(s) - chemistry , acetylene , piperazine , ethanol , salt (chemistry) , organic chemistry , stereochemistry , medicinal chemistry
A four step synthesis of [5,6‐ 14 C]‐eicosa‐5,8,11‐triynoic acid ( 1 ) from [ 14 C]‐labelled acetylene is described. [ 14 C 2 ]‐acetylene was converted to 5‐chloro‐[1,2‐ 14 C]‐pentyne via reaction of its monolithium salt with 3‐bromo‐1‐chloropropane. The doubly labelled 5‐chloropentyne thus obtained was transformed to [5,6‐ 14 C]‐hex‐5‐ynoic acid which was then coupled with 1‐chloro‐tetradeca‐2,5‐diyne to give the title compound. Using 2‐(2‐aminoethoxy)ethanol and 1‐(2‐hydroxyethyl)piperazine, amides ( 2 ) and ( 3 ), which had previously been found to be potent inhibitors of the 5‐lipoxygenase enzyme, were prepared from [ 14 C]‐labelled eicosatriynoic acid by way of acylimidazole chemistry.