A C Chang
Research Triangle Park Laboratories, Inc., Raleigh, NC, USA

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Publications (2)7.8 Total impact

  • Article: Synthesis and transporter binding properties of (R)-2 beta, 3 beta- and (R)-2 alpha, 3 alpha-diaryltropanes.
    S Jiang, A C Chang, P Abraham, M J Kuhar, F I Carroll
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    ABSTRACT: (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.
    Bioorganic & Medicinal Chemistry Letters 01/1999; 8(24):3689-92. · 2.55 Impact Factor
  • Article: Synthesis and transporter binding properties of 2,3-diphenyltropane stereoisomers. Comparison to 3beta-phenyltropane-2beta-carboxylic acid esters.
    A C Chang, J P Burgess, S W Mascarella, P Abraham, M J Kuhar, F I Carroll
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    ABSTRACT: 2beta,3beta-Diphenyl-(5), 2alpha,3alpha-diphenyl-(6), and 2alpha,3beta-diphenyltropane (3) as well as 2,3-diphenyltrop-2-ene (4) were prepared in racemic form and assayed for inhibition of radioligand binding at the dopamine (DA), serotonin (5-HT), and norepinephrine (NE) transporters. Among all three transporters, compounds 4-6 bound the DA transporter with the highest affinity. The 2beta,3beta-diphenyltropane (5) bound the DA transporter with an IC50 value (28 nM) almost identical to that of 3beta-phenyltropane-2beta-carboxylic acid methyl ester (WIN 35,065-2) and has much greater selectivity relative to binding to the serotonin transporter. A comparison of the radioligand data from this study to radioligand data obtained on other WIN 35,065-2 analogs suggests that hydrophobicity of the C-2 substituent of some analogs of the WIN 35,065-2 class may be an important contributing factor to binding at the DA transporter.
    Journal of Medicinal Chemistry 05/1997; 40(8):1247-51. · 5.25 Impact Factor

Institutions

  • 1997
    • Research Triangle Park Laboratories, Inc.
      Raleigh, NC, USA
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