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Syntheses of colchicine and isocolchicine labelled with carbon‐11 or carbon‐13
Author(s) -
Kothari Paresh J.,
Finn Ronald D.,
Larson Steven M.
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.2580360603
Subject(s) - colchicine , chemistry , carbon 13 , chemical synthesis , stereochemistry , carbon fibers , high performance liquid chromatography , total synthesis , chromatography , biochemistry , in vitro , medicine , physics , materials science , quantum mechanics , composite number , composite material
The syntheses of isotopically labelled (−)‐10‐[ 11 C/ 13 C]‐colchicine and (−)‐9‐[ 11 C/ 13 C]‐ isocolchicine have been achieved from the reaction of (−)desmethylcolchicine with [ 11 C/ 13 C]‐iodomethane. The radiolabelled compounds, (−)‐10‐[ 11 C]‐colchicine ( 11 C‐n‐colchicine) and (−)‐9‐[ 11 C]‐isocolchicine ( 11 C‐i‐colchicine), were isolated by reversed phase HPLC. The total synthesis time was approximately 60 minutes for both radiolabelled compounds with an average specific activity of 240 mCi/μmol calculated to EOB. Utilizing a similar synthetic strategy, we also report the synthesis of milligram quantities of the carbon‐13 enriched compounds and the magnetic resonance signal assignment for (−)‐9‐[ 13 C] isocolchicine.