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Synthesis of position‐specific tritium‐labeled 20( S )‐camptothecin, 9‐amino‐20( S )‐camptothecin, and 10,11‐methylenedioxy‐20( S )‐camptothecin
Author(s) -
Nicholas Allan W.,
Wani Mansukh C.,
Wall Monroe E.,
Kepler John A.,
Taylor George F.
Publication year - 1993
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.2580330907
Subject(s) - camptothecin , methylenedioxy , chemistry , stereochemistry , catalysis , tritium , aryl , amino acid , medicinal chemistry , organic chemistry , biochemistry , halogen , alkyl , physics , nuclear physics
The synthesis is given for three ring A tritiated camptothecin (CPT) analogs as biological probes in the study of the parent compounds which are of current widespread interest as potent anticancer agents. The strategy of catalytic tritolysis of aryl halide bonds was employed, and thus the preparations of the requisite precursors 9‐chloro‐20( S )‐CPT ( 9 ), 9‐amino‐10,12‐dibromo‐20( S )‐CPT ( 14 ), and 9‐chloro‐10,11‐methylenedioxy‐20( S )‐CPT ( 18 ) are given; catalytic tritiation of these respective precursors under polar, alkaline solvent conditions using palladium/carbon provides smooth conversion to [9‐ 3 H]‐20( S )‐CPT ( 10 ), 9‐amino‐[10,12‐ 3 H]‐20( S )‐CPT ( 15 ), and [9‐ 3 H]‐10,11‐methylenedioxy‐20( S )‐CPT ( 19 ).