Synthesis and in vitro evaluation of tetrahydroisoquinolinyl benzamides as ligands for σ receptors was written by Xu, Rong;Lever, John R.;Lever, Susan Z.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Category: tetrahydroisoquinoline This article mentions the following:
5-Bromo-N-[4-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-butyl]-2,3-dimethoxy-benzamide (I) is one of the most potent and selective σ 2 receptor ligands reported to date. Previous structure-activity relationship studies of such tetrahydroisoquinolinyl benzamides have focused on the linker that connects the ring systems and the effects of benzamide ring substituents. The present study explores the effects of fusing methylene-, ethylene-, and propylenedioxy rings onto the tetrahydroisoquinoline in place of the two methoxy groups. These modifications decreased σ2 affinity by 8- to 12-fold, with no major differences noted with ring size. By contrast, the methylenedioxy analog showed a 10-fold greater σ1 affinity than I, and progressively lower σ1 affinities were then noted with increasing ring size. The tetrahydroisoquinoline ring of I was opened to study the effects of greater conformational fluidity on σ receptor binding. The σ2 affinity of the open-ring compound decreased by 1700-fold, while σ1 affinity was not changed. Thus, a constrained tetrahydroisoquinoline ring system is key to the exceptional σ2 receptor binding affinity and selectivity of this active series. In the experiment, the researchers used many compounds, for example, 6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3Category: tetrahydroisoquinoline).
6,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (cas: 2328-12-3) belongs to tetrahydroisoquinoline derivatives. The tetrahydroisoquinoline skeleton is encountered in a number of bioactive compounds and drugs. Because of the high biological relevance of compounds possessing the 1,2,3,4-tetrahydroisoquinoline framework, a large number of synthetic approaches towards the creation of an isoquinoline or 1,2,3,4-tetrahydroisoquinoline core are presently known. However, synthetic routes to tetrahydroisoquinoline derivatives containing fluorine atom(s) in their structure are not particularly abundant.Category: tetrahydroisoquinoline
Referemce:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem