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Convenient synthesis of [2‐ 14 C]‐methylglyoxal bis(guanylhydrazone), [ 14 C]‐mitoguazone
Author(s) -
Burgos Alain,
Ellames George J.
Publication year - 1995
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.2580360112
Subject(s) - chemistry , methylglyoxal , yield (engineering) , acetone , potassium , sodium , salt (chemistry) , medicinal chemistry , radiochemistry , organic chemistry , materials science , metallurgy , enzyme
Abstract [2‐ 14 C]‐Methylglyoxal bis(guanylhydrazone) dihydrochloride, [ 14 C]‐mitoguazone, 3, has been prepared in three steps from potassium [1‐ 14 C]‐acetate in an overall radiochemical yield of 16%. The key steps in this procedure are the formation of the sodium salt of [ acetone ‐2‐ 14 C]‐methylsulfinylacetone, 5 , and Pummerer rearrangement to the [ 14 C] labelled hemithioacetal, 6 , which is trapped with two equivalents of aminoguanidine to afford the desired [ 14 C] mitoguazone, 3 .