3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-car bonitriles for SERT imaging: chemical synthesis, evaluation in vitro and radiofluorination.

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Funke U, Fischer S, Hiller A, Scheunemann M, Deuther-Conrad W, Brust P, Steinbach J

3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-car bonitriles for SERT imaging: chemical synthesis, evaluation in vitro and radiofluorination.

Bioorg Med Chem Lett. 2008 Aug 15;18(16):4727-30. doi: 10.1016/j.bmcl.2008.06.077. Epub 2008 Jun 28.

PubMed ID

18644726 [ View in PubMed

]

Abstract

Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as (18)F-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful (18)F-fluoroalkylation of one pair of compounds are described herein.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Citalopram	Sodium-dependent serotonin transporter	Ki (nM)	4.38	N/A	N/A	Details
Citalopram	Sodium-dependent serotonin transporter	Ki (nM)	32.8	N/A	N/A	Details
Paroxetine	Sodium-dependent serotonin transporter	Ki (nM)	0.42	N/A	N/A	Details
Paroxetine	Sodium-dependent serotonin transporter	Ki (nM)	0.38	N/A	N/A	Details