Premium
Synthesis of mitomycin C labeled with mono‐tritium at the C6 ‐ methyl position
Author(s) -
Kanda Yutaka,
Akinaga Shiro,
Kasai Masaji
Publication year - 1990
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.2580280907
Subject(s) - chemistry , tritium , aziridine , yield (engineering) , ethylenedioxy , mitomycin c , radiochemistry , reductive amination , hydride , chemical synthesis , organic chemistry , in vitro , catalysis , hydrogen , biochemistry , medicine , ring (chemistry) , physics , materials science , alkyl , surgery , nuclear physics , metallurgy
A first preparation of mitomycin C specifically labeled with mono‐tritium at the C6‐methyl position is described. The key intermediate in the synthesis, 7,7‐ethylenedioxy‐6‐methylenemitosane ( 5 ) was made by treating 7,7‐ethylenedioxy‐6‐phenylselenomitosane ( 4 ) with meta‐chloroperbenzoic acid. Subsequent 1,4‐addition of [ 3 H]hydride gave 7,7‐ethylenedioxymitosane labeled with tritium ( 6 ). Amination at C7 position and deacetylation of 1a‐aziridine nitrogen of 6 gave [C6‐CH 3 ‐ 3 H 1 ] mitomycin C ( 2 ) with an overall yield of 15%. The specific activity of the final compound was 16.2 mCi/mmol with 13% tritium incorporation.