0000000000805176
AUTHOR
Chyng-yann Shiue
Radiosynthesis of 1-(4-(2-[18F]fluoroethoxy)benzenesulfonyl)-3-butyl urea: a potentialβ-cell imaging agent
Summary Tolbutamide (1) is a sulfonurea agent used to stimulate insulin secretion in type 2 diabetic patients. Its analogue 1-(4-(2-[ 18 F]fluoroethoxy)benzenesulfonyl)-3butyl urea (3) was synthesized in overall radiochemical yields of 45% as a potential b-cell imaging agent. Compound 3 was synthesized by 18 F-fluoroalkylation of the corresponding hydroxy precursor (2 )w ith 2-[ 18 F]fluoroethyltosylate in DMF at 1208C for 10 min followed by purification with HPLC in a synthesis time of 50 min. Insulin secretion experiments of the authentic 19 F-standard compound on rat islets showed that the compound has a similar stimulating effect on insulin secretion as that of tolbutamide (1). The part…
Synthesis of fluorine-18 labeled sulfonureas as ?-cell imaging agents
Tolbutamide (1) and glyburide (7) are hypoglycemic drugs used to stimulate insulin secretion in type 2 diabetic patients. We have synthesized their fluorine-18 labeled analogs, 1-[(4-[ 18 F]fluorobenzenesulfonyl)]-3-butyl]urea (p-[ 18 F]fluorotolbutamide, 3a) and N-{4-[β-(2-[ 18 F]fluoroethoxybenzene carboxamido)ethyl]benzenesulfonyl)-N'-cyclohexylurea (2-[ 18 F]fluoroethoxyglyburide, 6a) as β-cell imaging agents. Compound 3a was synthesized via two approaches: One-step synthesis via nucleophilic substitution of p-nitrotolbutamide (2) with K[ 18 F]/Kryptofix 2.2.2 in either CH 3 CN or DMSO gave a complicated mixture; a two-step synthesis via preparation and reaction of 4-[ 18 F]fluorobenzen…