Bis-tetrahydroisoquinoline derivatives: structure analysis of the three stereoisomers of 1,1'-(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline).

  title={Bis-tetrahydroisoquinoline derivatives: structure analysis of the three stereoisomers of 1,1'-(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline).},
  author={Johan Wouters and Kossay Elasaad and Bernadette Norberg and Amaury Graulich and Jean-François Li{\'e}geois},
  journal={European journal of medicinal chemistry},
  volume={45 7},
Crystal structure of the three stereoisomers of 1,1'-(propane-1,3-diyl)-bis-(6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline) hydrochloride after resolution by semi-preparative chiral HPLC establishes the absolute configuration and conformation. 
5 Citations
Structural analysis of some bis-(8-isopropyl-isoquinolinium) derivatives reveals a preferential folded conformation leading to a stereoselective attack by sodium borohydride
Abstract Reduction of symmetrical bis-isoquinolinium derivatives with sodium borohydride generates normally a mixture of three 1,2,3,4-tetrahydroisoquinoline stereoisomers. In a series of 8-isopropyl
The stereochemistry of isoquinoline Reissert compounds: a unique platform for observation of steric and electronic interactions
Abstract Isoquinoline Reissert compounds (2-acyl-1,2-dihydroisoquinaldonitriles) with either 3-H (1) or 3-CH3 (2) substituents and various N-acyl groups have been examined in detail by 1H and 13C NMR
Electronically Rich N-Substituted Tetrahydroisoquinoline 3-Carboxylic Acid Esters: Concise Synthesis and Conformational Studies.
Three complementary, glycine donor-based strategies for high yielding synthesis of highly substituted, electronically rich THIQ3CA esters are described and fundamental studies on the synthesis and conformational properties are presented.
Stereochemistry of alkylated isoquinoline Reissert compounds
Abstract A series of alkylated isoquinoline Reissert compounds (2-acyl-1-alkyl-1,2-dihydroisoquinoline-1-nitriles) with either 3-H (3) or 3-CH3 (4) substituents was examined by 1H, 13C, and 19F NMR
Synthesis and radioligand binding studies of bis-(8-isopropyl-isoquinolinium) derivatives as ligands for apamin-sensitive sites on cloned SK2 and SK3 channels.
Molecular studies showed that the optimal conformation of compound 2d fits well with the SK pharmacophore model, with the m-xylyl derivative having the best profile in terms of affinity and selectivity for SK3/SK2 channels.


(−)-1-methylcorypalline, an isoquinoline alkaloid from Arthrocnemum glaucum
Abstract Two isoquinoline alkaloids, (±)-1,2-dimethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline [(±)-carnegine] and (−)-1,2-dimethyl-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline
Synthesis and radioligand binding studies of bis-isoquinolinium derivatives as small conductance Ca(2+)-activated K(+) channel blockers.
The original bis-isoquinolinium derivatives were synthezised and evaluated using binding studies, electrophysiology, and molecular modeling and demonstrate the blocking potential of the apamin-sensitive after-hyperpolarization.
Bis-tetrahydroisoquinoline derivatives: AG525E1, a new step in the search for non-quaternary non-peptidic small conductance Ca(2+)-activated K(+) channel blockers.
AG525E1 is the discovery of a chiral bis-tertiary amine with SK blocking properties from chemical modulation of laudanosine, which has an affinity for SK channels and can reach central SK targets.
The conformation of six-membered rings
Although an indefinite number of conformations exists for six-mem- bered rings, and although there is general consensus about the six classical forms (Bucourt and Hainaut, 1965; Cano et al., 1977;
General definition of ring puckering coordinates
A unique mean plane is defined for a general monocyclic puckered ring. The geometry of the puckering relative to this plane is described by amplitude and phase coordinates which are generalizations
On enantiomorph‐polarity estimation
The behaviour of Rogers's η parameter for enantiomorph-polarity estimation is examined theoretically and experimentally on simulated intensity data for seven well-assorted compounds. An alternative
Electrophysiological characterization of the SK channel blockers methyl‐laudanosine and methyl‐noscapine in cell lines and rat brain slices
Both methyl‐laudanosine and methyl‐noscapine are medium potency, quickly dissociating, SK channel blockers with a similar potency on the three SK subtypes and may be superior in terms of specificity for the SK channels.
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.
Small conductance calcium-activated potassium (SK) channels are found in many types of neurons as well as in some other cell types, and are heavily expressed in the basal ganglia and in the limbic system, suggesting that they may modulate motricity and emotional behaviour.
SK channels control the firing pattern of midbrain dopaminergic neurons in vivo
The first demonstration of a major role of SK channels in the control of the switch between tonic and burst firing of dopaminergic neurons in physiological conditions is provided, which suggests a new strategy to develop modulators of the dopamine (DA) system.
A short history of SHELX.
  • G. Sheldrick
  • Medicine, Chemistry
    Acta crystallographica. Section A, Foundations of crystallography
  • 2008
This paper could serve as a general literature citation when one or more of the open-source SH ELX programs (and the Bruker AXS version SHELXTL) are employed in the course of a crystal-structure determination.