Synthesis and transporter binding properties of (R)-2 beta,3 beta- and (R)-2 alpha,3 alpha-diaryltropanes
Jiang, S. C., Chang, A. C., Abraham, P., Kuhar, M. J., & Carroll, F. (1998). Synthesis and transporter binding properties of (R)-2 beta,3 beta- and (R)-2 alpha,3 alpha-diaryltropanes. Bioorganic and Medicinal Chemistry Letters, 8(24), 3689-3692.
(R)-2-Aryl-2-tropinone (9) was synthesized from (R)-2-carbomethoxy-3-tropinone (5) and was used as the key intermediate for the synthesis of (R)-2 beta,3 beta- and (R)-2 alpha,3 alpha-diaryltropanes. Inhibition of radioligand binding studies at the dopamine, serotonin, and norepinephrine transporters showed that the (R)-3 beta-(4-methylphenyl)-2 beta-phenyltropane (3b, RTI-422) possessed an IC50 value of 1.96 nM at the dopamine transporter and was highly selective for this transporter relative to the serotonin and norepinephrine transporters. (C) 1998 Elsevier Science Ltd. All rights reserved