Synthesis of novel (benzimidazolyl)isoquinolinols and evaluation as adenosine A1 receptor tools

Abstract

Mild, metal free aromatization of tetrahydroisoquinolinols. Synthesis of (benzimidazolyl)isoquinolinols.

Mild Synthesis of Fluorosolvatochromic and Acidochromic 3-Hydroxy-4-pyridylisoquinoline Derivatives from Easily Available Substrates

“…5 If necessary, the initially formed tetrahydroisoquinolinol has to be subsequently oxidized. 6 More recently, it has been demonstrated that 3-hydroxyisoquinolines are available with significantly milder methods, for example, from B(C 6 F 5 )-/Co-catalyzed C−H bond activation reactions of imines with diazo compounds 7 or by a sequence of Ugi reaction and Pd-mediated Heck cyclization. 8 Herein, we present a novel synthetic route to 3-hydroxyisoquinoline derivatives that we incidentally discovered in failed attempts to functionalize halogenated benzo [b]quinolizinium derivatives 1b−e by nucleophilic substitution.…”

“…Thus, 3-hydroxyisoquinoline derivatives are available by the traditional cyclization methodsusually under harsh conditionswith the formation of the N-heterocyclic ring as the key step . If necessary, the initially formed tetrahydroisoquinolinol has to be subsequently oxidized . More recently, it has been demonstrated that 3-hydroxyisoquinolines are available with significantly milder methods, for example, from B­(C 6 F 5 )-/Co-catalyzed C–H bond activation reactions of imines with diazo compounds or by a sequence of Ugi reaction and Pd-mediated Heck cyclization .…”

Development and Application of Subtype-Selective Fluorescent Antagonists for the Study of the Human Adenosine A1 Receptor in Living Cells

“…binding affinity to the A 1 AR. 54 Therefore, there still remains a need for fluorescent probes with marked subtype selectivity for the A 1 AR.…”

“…For example, Singh et al designed fluorescent ligands based on a (benzimidazolyl)­isoquinolinol scaffold. However, these probes did not show measurable binding affinity to the A 1 AR . Therefore, there still remains a need for fluorescent probes with marked subtype selectivity for the A 1 AR.…”