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The synthesis of N 1 , N 11 ‐diethyl[6‐ l4 C]norspermine ([ 14 C]CI‐1006), a new anticancer drug
Author(s) -
Hicks James L.,
Huang Yun
Publication year - 1997
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/(sici)1099-1344(199704)39:4<275::aid-jlcr978>3.0.co;2-7
Subject(s) - chemistry , yield (engineering) , salt (chemistry) , condensation , diethyl malonate , propane , molecule , medicinal chemistry , diamine , combinatorial chemistry , organic chemistry , catalysis , materials science , physics , metallurgy , thermodynamics
N 1 , N 11 Diethylnorspermine, CI‐1006, a potential new anticancer drug, was synthesized with a carbon‐14 located at the central carbon of the molecule. Condensation of N‐(2,4,6‐trimethylbenzenesulfonyl)‐N‐ethyl‐propane‐1,3‐diamine with diethy[2‐ 14 C]malonate gave a symmetrical diamide. The resulting protected diamide was reduced and deprotected in one pot to give the product as the tetrahydrobromide salt. A salt conversion gave the desired tetrahydrochloride. A total of 26.9 mCi of material was made with a specific activity of 26.1 mCi/mmol. The overall yield was 38%. © 1997 John Wiley & Sons, Ltd.