Corypalline and O-methylcorypalline, two alkaloids from Papaver bracteatum

Theuns, Hubert G.; Vlietstra, Edward J.; Salemink, C. A.

doi:10.1016/s0031-9422(00)80099-0

Cited by 18 publications

(12 citation statements)

References 15 publications

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“…The mass spectrometrical fragmen-*Part 6 in the Series; for part 5 see ref. [7]. tations of these two compounds showed strong resemblances to those reported for the naturally occurring Menispermaceae dibenz[d, flazonine alkaloids laurifonine (3), laurifinine (4)and laurifine (5) [8,9].…”

Section: Resultssupporting

confidence: 55%

Neodihydrothebaine and bractazonine, two dibenz[d,f]azonine alkaloids of Papaver bracteatum

et al. 1984

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Section: Resultssupporting

confidence: 55%

Neodihydrothebaine and bractazonine, two dibenz[d,f]azonine alkaloids of Papaver bracteatum

et al. 1984

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“…The nicotinic acetylcholine receptors (nAChRs), a heterogeneous family of ligand-gated ion channels widely distributed throughout the peripheral and central nervous systems, are involved in a broad range of psychiatric and neurodegenerative disorders such as schizophrenia, attention deficit hyperactivity disorder, depression, Alzheimer’s and Parkinson’s diseases, pain, and substance abuse. − Considerable efforts have been put into the design of agonists (based on scaffolds such as nicotine, varenicline, cytisine, and epibatidine) as well as positive allosteric modulators targeting the neuronal nAChRs. − In comparison, antagonists are far less studied despite their substantial therapeutic potential. − Most of the available nAChR antagonists are natural products such as methyllycaconitine (MLA), α-bungarotoxin, ibogaine, d -tubocurarine, α-conotoxins, and dihydro-β-erythroidine (DHβE), the latter being a widely used selective antagonist of β2-containing heteromeric nAChRs and a semisynthetic member of the Erythrina alkaloid family. , We recently reported the design, synthesis, and pharmacological evaluation of 21 analogues of aromatic Erythrina alkaloids as nAChR antagonists and found that the structurally simple tetrahydroisoquinoline 1 (also known as O -methylcorypalline) , displayed submicromolar binding affinity at the α4β2 nAChR and more than 300-fold binding selectivity over the α4β4, α3β4, and α7 subtypes (see Figure A) …”

Section: Introductionmentioning

confidence: 99%

“…10−20 Most of the available nAChR antagonists are natural products such as methyllycaconitine (MLA), α-bungarotoxin, ibogaine, D-tubocurarine, α-conotoxins, and dihydro-β-erythroidine (DHβE), the latter being a widely used selective antagonist of β2containing heteromeric nAChRs and a semisynthetic member of the Erythrina alkaloid family. 21,22 We recently reported the design, synthesis, and pharmacological evaluation of 21 analogues of aromatic Erythrina alkaloids as nAChR antagonists and found that the structurally simple tetrahydroisoquinoline 1 (also known as O-methylcorypalline) 23,24 displayed submicromolar binding affinity at the α4β2 nAChR and more than 300fold binding selectivity over the α4β4, α3β4, and α7 subtypes (see Figure 1A). 25 Ligands containing quaternary nitrogens have previously been shown to possess high activity at the nAChR.…”

Section: ■ Introductionmentioning

confidence: 99%

Dual Nicotinic Acetylcholine Receptor α4β2 Antagonists/α7 Agonists: Synthesis, Docking Studies, and Pharmacological Evaluation of Tetrahydroisoquinolines and Tetrahydroisoquinolinium Salts

et al. 2018

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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 K and functional IC 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 DHβΕ. 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.

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“…236°( Et0H/Et20) (11), 233-234° (13) UV: (HC1) (EtOH) 220sh (3.81), 226 (3.85), (3.23), 285 (3.20) (9) IR: (HC1) (KBr) (12,20) 247-248.5°(MeOH) (9) UV: (iPrOH) 274 (3.26), 280 (3.26) (12) (0. IN KOH) 241 (3.94), 388 UV: (EtOH) 227 , 286 (3.44) (26,25) (EtOH/NaOH) 247 (3.69), 301 (3.55) (26) NMR: 90 MHz (DMSO-4) (23) 100 MHz (acetone-a^(24) MS: 194 (6), 193 (43), 192 (69), 177 (20), 164 (5), 151(13), 150 (100), 148 (6), 135 (21), 107 06) (23,25) Sources:…”

mentioning

confidence: 99%

“…Berberidaceae: Berberís oblonga (25) Fumariaceae: Corydalis stricta ( 27) Synthetic (17,22,23) 11. CORYP ALUNE CnH15N02 193.1099 MP: 168°( MeOH/Et20) (29,30) 6.44…”

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