Serotonergic and dopaminergic activities of rigidified ( R )-aporphine derivatives

Linnanen, Tero; Brisander, Magnus; Mohell, Nina; Johansson, Anette M.

doi:10.1016/s0960-894x(00)00655-7

Cited by 24 publications

(27 citation statements)

References 23 publications

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“…[a] Reagents and conditions: (i) (COCl) 2 ride 5 by reaction with oxalyl chloride followed by treatment with the desired 2-phenyl ethylamine 4. These reactions occur in good yield, typically 72-99 % yield (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…[a] Reagents and conditions: (i) Method A: POCl 3 , CH 2 Cl 2 , reflux, 12 h; (ii) Method B: Polyphosphoric acid, 150°C, 12 h; (iii) NaBH 4 , MeOH, 25°C, 3 h; (iv) (ROC) 2 The amines were then protected as tert-butyl carbamates (Boc), methyl carbamates, acetates (Ac) as well as a paratoluenesulfonamides (Ts) in 54-88 % yields (Table 2).…”

Section: Resultsmentioning

confidence: 99%

“…[a] Reaction conditions: isoquinoline 9a-n, Pd(OAc) 2 the synthesis of the aporphine core (Scheme 3). In subsequent studies, we discovered that this particular catalyst system was unable to achieve completion when employing less than 3 mol-% catalyst loading with aryl bromides (Entry 2) and failed to induce arylation using aryl chlorides.…”

Section: Resultsmentioning

confidence: 99%

“…[17] The aryl chloride (0.1 g, 0.28 mmol, 1.0 equiv. ), (o-biphenyl)P(Cy) 2 (0.020 g, 0.06 mmol, 0.2 equiv. ), NaOtBu (0.038 g, 0.39 mmol, 1.4 equiv.)…”

Section: Methods Bmentioning

confidence: 99%

“…[1] They share a characteristic tetracyclic motif with different levels of oxidation on both aromatic rings (Scheme 1). A range of interesting biological activities has been documented, including serotonergic, [2] antiplatelet, [3] anticancer, [4] antimalarial [5] and vasorelaxing activity. [6] These properties have prompted intensive structure-activity relationship (SAR) studies over the past three decades.…”

Section: Introductionmentioning

confidence: 99%

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Aporphine Alkaloid Synthesis and Diversification via Direct Arylation

2007

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Palladium‐catalyzed direct arylation of aryl chlorides, bromides and iodides has been applied to the preparation of new aporphine analogues including C2‐substituted aporphines by reaction with benzodioxole, pyridine N‐oxide and pyrazine N‐oxide. Successful application of direct arylation in these diversification reactions highlights its utility not only in convergent, but also in divergent synthesis. We also describe enantioselective syntheses of (R)‐nornuciferine and (R)‐nuciferine employing a catalytic asymmetric transfer hydrogenation in high yield and excellent enantiomeric excess. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…[17] The aryl chloride (0.1 g, 0.28 mmol, 1.0 equiv. ), (o-biphenyl)P(Cy) 2 (0.020 g, 0.06 mmol, 0.2 equiv. ), NaOtBu (0.038 g, 0.39 mmol, 1.4 equiv.)…”

Section: Methods Bmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Aporphine Alkaloid Synthesis and Diversification via Direct Arylation

2007

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ChemInform Abstract: Serotonergic and Dopaminergic Activities of Rigidified (R)‐Aporphine Derivatives.

et al. 2001

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Discovery of Aporphine Analogues as Potential Antiplatelet and Antioxidant Agents: Design, Synthesis, Structure–Activity Relationships, Biological Evaluations, and in silico Molecular Docking Studies

et al. 2018

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To explore the potential of aporphine alkaloids, a novel series of functionalized aporphine analogues with alkoxy (OCH , OC H , OC H ) functional groups at C1/C2 of ring A and an acyl (COCH and COPh) or phenylsulfonyl (SO Ph and SO C H -3-CH ) functionality at the N6 position of ring B of the aporphine scaffold were synthesized and evaluated for their arachidonic acid (AA)-induced antiplatelet aggregation inhibitory activity and 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging antioxidant activity, with acetylsalicylic acid and ascorbic acid as standard references, respectively. The preliminary structure-activity relationship related to AA-induced platelet aggregation inhibitory activity results showed that the aporphine analogues 1-[1,2,9,10-tetramethoxy-6a,7-dihydro-4H-dibenzo[de,g]quinolin-6(5H)-yl]ethanone and 1-[2-(benzyloxy)-1,9,10-trimethoxy-6a,7-dihydro-4H-dibenzo[de,g]quinolin-6(5H)-yl]ethanone to be the best compounds of the series. Moreover, the DPPH free-radical-scavenging antioxidant activity results demonstrated that the aporphine analogues 1,2,9,10-tetramethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, 2-ethoxy-1,9,10-trimethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, 1-ethoxy-2,9,10-trimethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, 2,9,10-trimethoxy-6-(methylsulfonyl)-1-propoxy-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline, and 1-(benzyloxy)-2,9,10-trimethoxy-6-(methylsulfonyl)-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline were the best compounds of the series. Moreover, in silico molecular docking simulation studies of the active analogues were also performed.

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Serotonergic and dopaminergic activities of rigidified ( R )-aporphine derivatives

Cited by 24 publications

References 23 publications

Aporphine Alkaloid Synthesis and Diversification via Direct Arylation

Aporphine Alkaloid Synthesis and Diversification via Direct Arylation

ChemInform Abstract: Serotonergic and Dopaminergic Activities of Rigidified (R)‐Aporphine Derivatives.

Discovery of Aporphine Analogues as Potential Antiplatelet and Antioxidant Agents: Design, Synthesis, Structure–Activity Relationships, Biological Evaluations, and in silico Molecular Docking Studies

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