193882-73-4

Upstream product

• 119-30-2 2-hydroxy-5-iodobenzoic acid 
• 4068-75-1 methyl 5-iodosalicylate 
• 824430-95-7 2-(2-fluoro-ethoxy)-5-iodo-benzoic acid 2-fluoro-ethyl ester 
• 193882-74-5 methyl 2-(2-fluoroethoxy)-5-iodobenzoate 

Downstream Products

• 1269797-39-8 2-(2-fluoroethoxy)-5-iodo-N-(4-(4-(2-methoxyphenyl)piperazin-1-yl)-trans-butyl-2-enyl)benzamide 
• 1609428-83-2 N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-5-(4-((dimethylamino)methyl)-1H-1,2,3-triazol-1-yl)-2-(2-fluoroethoxy)benzamide 
• 1609429-18-6 5-azido-N-(4-(6,7-dimethoxy-3,4-dihydroisoquinolin-2(1H)-yl)butyl)-2-(2-fluoroethoxy)benzamide 

Relevant academic research and scientific papers

Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands

Two novel classes of compounds targeting the sigma-2 (σ2) receptor were synthesized, and their bioactivities to binding σ1 and σ2 receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the σ2 receptor. These data suggest 11C-labeled versions of these compounds may be potential σ2-selective radiotracers for imaging the proliferative status of solid tumors.

Synthesis and pharmacological evaluation of fluorine-containing D 3 dopamine receptor ligands

A series of fluorine-containing N-(2-methoxyphenyl)piperazine and N-(2-fluoroethoxy)piperazine analogues were synthesized, and their affinities for human dopamine D2, D3, and D4 receptors were determined. Radioligand binding studies identified five compounds, 18a, 20a, 20c, 20e, and 21e, which bind with high affinity at D3 (K i = 0.17-5 nM) and moderate to high selectivity for D3 vs D2 receptors (ranging from ～25- to 163-fold). These compounds were also evaluated for intrinsic activity at D2 and D3 receptors using a forskolin-dependent adenylyl cyclase assay. This panel of compounds exhibits varying receptor subtype binding selectivity and intrinsic activity at D2 vs D3 receptors. These compounds may be useful for behavioral pharmacology studies on the role of D2-like dopamine receptors in neuropsychiatric and neurological disorders. Furthermore, compound 20e, which has the highest binding affinity and selectivity for the D3 receptor (Ki = 0.17 nM for D3, 163-fold selectivity for D3 vs D2 receptors), represents a candidate fluorine-18 radiotracer for in vivo PET imaging studies on the regulation of D3 receptor expression.

Synthesis and 5-HT-3 receptor binding activity of 5-[125I]iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl]benzamide and its 5-halogen-2-alkoxyl homologues

(S)-5-Iodo-2,3-dimethoxy-N-(1-azabicyclo[2.2.2]oct-3-yl)benzamide (MIZAC) was prepared from 5-iodo-2,3-dimethoxybenzoyl chloride and (S)-3-aminoquinuclidine. [125I]Iodode-stannylation of its corresponding 5-tri-n-butyltin derivative gave [125I]-MIZAC at 1800 Ci/mmol. Binding of [125I]-MIZAC in rat entorhinal cortex revealed a K(D) of 1.37 ± 0.21 nM. A series of racemic 2-O-alkyl derivatives of MIZAC were prepared and 5-HT-3 receptor affinities were determined by inhibition of [125I]-MIZAC binding. Optimal affinity for the receptor was obtained with small, electron-withdrawing substituents in the aromatic 5-position and with bulky substituents in the 3-position. [125I]-MIZAC is a selective radioligand useful for in vitro identification of the 5-HT-3 receptor.