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Novel synthesis of [ 18 F]‐fluorobenzene and pyridinecarbohydrazide‐folates as potential PET radiopharmaceuticals
Author(s) -
Al Jammaz I.,
AlOtaibi B.,
Okarvi S.,
Amartey J.
Publication year - 2006
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.1022
Subject(s) - chemistry , fluorobenzene , pharmacology , combinatorial chemistry , organic chemistry , medicine , benzene
In an attempt to visualize folate receptors that over‐express on many cancers, [ 18 F]‐fluorobenzene and pyridine carbohydrazide‐folates were synthesized using two different synthetic approaches starting from nucleophilic displacement reactions on ethyl‐trimethylammonium‐benzoate and pyridine carboxylate precursors. The intermediates ethyl [ 18 F]‐fluorinated benzene and pyridine esters were reacted with hydrazine to produce the [ 18 F]‐fluorobenzene and pyridine carbohydrazides followed by coupling with NHS‐folate 11 in the first approach. Whereas hydrazide‐folate 5 was reacted with 2,5‐dioxoazolidinyl [ 18 F]‐fluorobenzenecarboxylate in the second approach. Based on starting [ 18 F]‐fluoride, radiochemical yields and synthesis times were found to be around 80% (45 min) and 35% (80 min) for the first and the second approaches, respectively. The first synthetic approach holds considerable promise as a rapid and simple method for the radiofluorination of folic acid with high radiochemical yield and short time. Copyright © 2005 John Wiley & Sons, Ltd.