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Synthesis of estromustine, estramustine and estramustine phosphate labelled with deuterium
Author(s) -
Giribone Danilo,
Fontana Erminia
Publication year - 2004
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.809
Subject(s) - chemistry , estramustine , yield (engineering) , estrone , phosphate , deuterium , chloride , radiochemistry , phosphorylation , hydrolysis , medicinal chemistry , nuclear chemistry , organic chemistry , biochemistry , medicine , hormone , cancer , prostate disease , materials science , physics , prostate cancer , quantum mechanics , metallurgy
The preparation of estromustine (EoM), estramustine (EaM) and estramustine phosphate (EMP) specifically labelled with deuterium is reported. A two‐step, one‐pot procedure based on the reaction of N , N ‐ bis (2‐chloroethyl)carbamoyl chloride with the commercially available [2,4,16,16‐ 2 H 4 ]estrone ( 1 ) or [2,4,16,16,17‐ 2 H 5 ]estradiol ( 2 ) afforded [2,4,16,16‐ 2 H 4 ]estromustine ( 3 ) and [2,4,16,16,17‐ 2 H 5 ]estramustine ( 4 ), respectively. The phosphorylation of 4 followed by hydrolysis gave [2,4,16,16,17‐ 2 H 5 ]estramustine phosphate ( 5 ) in 65% chemical yield from 2 . Copyright © 2004 John Wiley & Sons, Ltd.