An enantioselective synthesis and biobehavioral evaluation of 7-fluoro-3-(p-fluorophenyl)-2-propyltropanes

Synthesis of 2β-Acyl-3β-(substituted naphthyl)-8-azabicyclo[3.2.1]octanes and Their Binding Affinities at Dopamine and Serotonin Transport Sites

“…3β (47), 278 (100), 250 (6), 193 (11), 178 (23), 165 (34), 153 (26) (10 mL) at 0 °C under Ar was added solid NO2BF4 (10.2 mg, 0.076 mmol) in one portion. The reaction mixture was stirred at 0 °C for 4 h, cooled to -10 °C and then ice (0.1 g) was added.…”

“…46 Consequently, there has been considerable recent interest in developing new methods for the construction of tropanes that would broaden the range of derivatives that would be available. 24,29,[47][48][49][50][51] We devised a general route for the synthesis of tropanes based on the reaction of vinylcarbenoids with pyrroles as illustrated in Scheme 1. 52,53 A design feature of this approach was the use of a ketone functionality at the C2-position instead of an ester.…”

Synthetic Approaches to Enantiomerically Pure 8-Azabicyclo[3.2.1]octane Derivatives

“…The likewise prepared and isolated exo diastereomer 115 was transformed into 2-propyl-3- p-F -phenyl-7- p -tolyl sulfoxide tropane derivative 116 (Scheme 29) . In this case, chemical modification of the p -tolyl sulfoxide moiety other than reduction was effected.…”

Synthesis and Biological Evaluation of 2-Substituted 3β-Tolyltropane Derivatives at Dopamine, Serotonin, and Norepinephrine Transporters

“…This broad class of compounds has provided tremendous insight into the nature of the dopamine transporter pharmacophore. The structural criteria for the 2-substituted 3-aryltropanes as high-affinity dopamine transporter ligands have been established for these positions, as well as for positions 6−8 of the tropane ring system. − From these studies it has been noted generally that a 4-substituted aryl group (e.g., tolyl) or a 3,4-disubstituted aryl group (e.g., 3,4-dichlorophenyl) at the 3β-position of the tropane ring affords compounds that exhibit high-affinity binding at dopamine transporters. The effects of substituents at the 2-position have also been extensively studied in terms of dopamine transporter affinity and selectivity.…”