Synthesis of a [18F]labeled chelidonine derivative as a possible antitumor agent.
[(+/-)-[5bRS-(5b alpha, 6beta, 12b alpha)]-5b,6,7,12b,13,14-hexahydro-13-methyl[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-1] phenanthridin-6-yl]-4-[18F]fluorobenzoate (6b) an aromatic ester of chelidonine was prepared as a possible PET radiotracer. Compound (6b) was prepared in no-carrier-added (n.c.a) form from the 4-N,N,N-trimethylanilinium triflate derivative (5) in one step. The best results were obtained using Kryptofix(2.2.2)/[18F] and DMSO as the solvent at 90 degrees C. Column chromatography afforded the desired compound in overall radiochemical yield of 65-70% (EOS) with a specific activity of about 3000 Ci/mmole and radiochemical purity greater than 95% in 15 min.
Jalilian
A R
AR
Department of Cyclotron, Nuclear Research Center for Agriculture and Medicine, Atomic Energy Organization of Iran, Karaj. ajalilian@pharmacy.ualberta.ca
Seyfi
P
P
Afarideh
H
H
Shafiee
A
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D053119:Benzophenanthridines; D001600:Berberine Alkaloids; D005462:Fluorine Radioisotopes; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008870:Microtubules / Q000187:drug effects; D010617:Phenanthridines; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D000970:Antineoplastic Agents; D053119:Benzophenanthridines; D001600:Berberine Alkaloids; D005462:Fluorine Radioisotopes; D010617:Phenanthridines; D019275:Radiopharmaceuticals; C062047:chelidonine