Synthesis of [14C]-labelled eicosa-5,8,11-triynoic acid and conversion to anti-inflammatory amides
✍ Scribed by W. R. Pilgrim; P. Nedoncelle; B. Shroot; J. Maignan; S. Restlé; L'Oréal
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- French
- Weight
- 303 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
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.