Discovery of 3-hydroxy-4-cyano-isoquinolines as novel, potent, and selective inhibitors of human 11β-hydroxydehydrogenase 1 (11β-HSD1)

Synthesis of 8-Alkoxy-5H-isochromeno[3,4-c]isoquinolines and 1-Alkoxy-4-arylisoquinolin-3-ols through Rh(III)-Catalyzed C–H Functionalization of Benzimidates with 4-Diazoisochroman-3-imines and 4-Diazoisoquinolin-3-ones

“…Using 1a and 8a as the reaction components, 9a was prepared in 75% yield. 14 Because of the structural uniqueness and importance in medicinal chemistry, 15 we further optimized the reaction conditions in detail (Table S1, see the Supporting Information). Optimal conditions were observed in the case where the reaction was performed at 100 °C in toluene using [Cp*RhCl 2 ] 2 /AgSbF 6 / AcOH as the catalyst system under an air atmosphere (Table S1, entry 16).…”

Fluorescence Properties of a Novel Isoquinoline Derivative Tested in an Invertebrate Chordate, Ciona intestinalis

“…3‐Hydroxyisoquinolines (ISOs) and their tautomeric isoquinolin‐3‐ones are rather unexplored heterocycles, even if they exhibit attractive biological activities. They have proven to strongly inhibit human 11β‐hydroxydehydrogenase 1 (11β‐HSD1), a privileged target for diabetes and/or metabolic syndrome [1] . ISO derivatives are also potent renal vasodilators [2] and inhibitors against Plasmodium falciparum cysteine protease falcipain‐2 [3] .…”

Divergent Syntheses of Isoquinolines and Indolo[1,2-a]quinazolines by Copper-Catalyzed Cascade Annulation from 2-Haloaryloxime Acetates with Active Methylene Compounds and Indoles

“…Nitrogen-containing heterocycles are an important subunit of alkaloidal compounds, which widely occur in natural products and pharmaceutical compounds . In fact, isoquinoline and its derivatives have recently been reported to be attractive azaheterocyclic skeletons, with the synthetic use for inhibitors of 11β-HSD1, anti-HIV, the precursor of dopamine agonist and antagonist, ion-channel blockers, chiral ligands, and phosphorescent emitters of OLEDs (Scheme ). The classic Bischler–Napieralski, Pomeranz–Fritsch, and Pictet–Spengler reactions opened the way to the preparation of isoquinolines .…”