24948-17-2Relevant articles and documents
Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts
Crestey, Fran?ois,Jensen, Anders A.,Soerensen, Christian,Magnus, Charlotte Busk,Andreasen, Jesper T.,Peters, Günther H. J.,Kristensen, Jesper L.
supporting information, p. 1719 - 1729 (2018/03/05)
We describe the synthesis of tetrahydroisoquinolines and tetrahydroisoquinolinium salts together with their pharmacological properties at various nicotinic acetylcholine receptors. In general, the compounds were α4β2 nAChR antagonists, with the tetrahydroisoquinolinium salts being more potent than the parent tetrahydroisoquinoline derivatives. The most potent α4β2 antagonist, 6c, exhibited submicromolar binding Ki and functional IC50 values and high selectivity for this receptor over the α4β4 and α3β4 nAChRs. Whereas the (S)-6c enantiomer was essentially inactive at α4β2, (R)-6c was a slightly more potent α4β2 antagonist than the reference β2-nAChR antagonist DHβη. The observation that the α4β2 activity resided exclusively in the (R)-enantiomer was in full agreement with docking studies. Several of tetrahydroisoquinolinium salts also displayed agonist activity at the α7 nAChR. Preliminary in vivo evaluation revealed antidepressant-like effects of both (R)-5c and (R)-6c in the mouse forced swim test, supporting the therapeutic potential of α4β2 nAChR antagonists for this indication.
A new convenient synthesis of phenanthrene alkaloids from 1-arylmethyl-1,2,3,4-tetrahydroisoquinolines
Kini,Ramana
, p. 4171 - 4173 (2007/10/03)
Hofmann degradation of 1-arylmethyl-1,2,3,4-tetrahydro-2,2- dimethylisoquinolinium iodides with methanolic KOH gave stilbene derivatives, for example, (E)-N-2{2-[2-(phenyl)ethenyl]-4,5-dimethoxyphenyl}ethyl-N,N- dimethylamine. Photochemical electrocycliza
ALKALOIDS FROM THE ROOTS OF Papaver pseudo-orientale (FEDDE) MEDW.
Veznik, Frantisek,Taborska, Eva,Sedmera, Petr,Dolejs, Ladislav,Slavik, Jiri
, p. 1752 - 1763 (2007/10/02)
Two new alkaloids, pseudorine (Ia) (quaternary benzyltetrahydroisoquinoline type) and pseudoronine (II) (benzil type), were isolated from the roots of Papaver pseudo-orientale (FEDDE) MEDW.This is a first occurence of this type of alkaloids in Papaveraceae.The main component of the tertiary alkaloid fraction was isothebaine accompanied by smaller amounts of orientalidine, mecambridine, bracteoline, nuciferine, protopine, and allocryptopine.The presence of salutaridine and papaverrubine D was established.Traces of coptisine and palmatine were also found in some samples.Strongly polar portion of the extract was converted to iodides.N-Methylisothebainium iodide (IIIa) (major component), pseudorine iodide (Ia), and corytuberine hydriodide (IV) (significant amounts), a minor alkaloids such as alborine iodide (alkaloid PO-5), pseudoronine (II), and magnoflorine iodide (IIIb) were isolated from this source.Structure of pseudorine was determined by UV, IR, 1H, and 13C NMR spectroscopy and using the correlation with laudanosine and codamine.Proposed structure of pseudoronine is based on the mass spectra comparison.
