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Synthesis of [C6‐CH 3 ‐ 14 C] and [C6‐CH 3 ‐ 3 H 3 ]mitomycin C
Author(s) -
Arai Hitoshi,
Kasai Masaji
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.2580290806
Subject(s) - chemistry , mitomycin c , iodide , ethylenedioxy , methyl iodide , chemical synthesis , ammonia , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry , in vitro , surgery , medicine , alkyl
A facile synthesis of the title compounds 2 and 3 is described. The key intermediate in the synthesis, 6‐demethyl‐7,7‐(ethylenedioxy)‐6‐(phenylselenenyl)mitosane ( 4 ) was synthesized in five steps from mitomycin A. Treatment of 4 with [ 14 C]methyl iodide in the presence of K 2 CO 3 afforded the [ 14 C]‐labelled mitosane ( 5 ). The removal of the phenylselenenyl group of 5 and subsequent treatment of the resultant mitosane 7 with ammonia led to the desired [ 14 C]mitomycin C (MMC) ( 2 ) with specific activity of 50 mCi/mmol. Similarly, [ 3 H]‐labelled MMC ( 3 ) with highly specific activity of 78.4 Ci/mmol was obtained.