ArticleBioorganic & medicinal chemistry2016
Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity.
Article in Bioorganic & medicinal chemistry, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 20 citations in OpenAlex.
- A Copper-Catalyzed Decarboxylative Olefination Cascade Enables Access to Protoberberine Alkaloid Frameworks.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Novel Halolactones Derived from Vanillin: Design, Synthesis, Structural Characterization, and Evaluation of Antiproliferative and Hemolytic Activities.Molecules (Basel, Switzerland) · 2025Article
- Natural Product-Inspired Dopamine Receptor Ligands.Journal of medicinal chemistry · 2024Review
- Fluoroalkoxylated C-3 and C-9 (S)-12-bromostepholidine analogues with D1R antagonist activity.Bioorganic chemistry · 2023Article
- First synthesis of thiazepino[3,4-a]isoquinolines, a facile new synthetic route to diazepino[3,4-a]isoquinolines and assessment of their dopamine and σ receptor affinities.Journal of heterocyclic chemistry · 2020Article
- Deep Learning in Drug Discovery and Medicine; Scratching the Surface.Molecules (Basel, Switzerland) · 2018Review
- Synthesis and evaluation of C9 alkoxy analogues of (-)-stepholidine as dopamine receptor ligands.European journal of medicinal chemistry · 2017Article
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Authors and funding
8 authors at 4 institutions in 1 country.
Funding
Abstract
Two series of analogues of the tetrahydroprotoberberine (THPB) alkaloid (±)-stepholidine that (a) contain various alkoxy substituents at the C10 position and, (b) were de-rigidified with respect to (±)-stepholidine, were synthesized and evaluated for affinity at dopamine and σ receptors in order to evaluate effects on D3 and σ2 receptor affinity and selectivity. Small n-alkoxy groups are best tolerated by D3 and σ2 receptors. Among all compounds tested, C10 methoxy and ethoxy analogues (10 and 11 respectively) displayed the highest affinity for σ2 receptors as well as σ2 versus σ1 selectivity and also showed the highest D3 receptor affinity. De-rigidification of stepholidine resulted in decreased affinity at all receptors evaluated; thus the tetracyclic THPB framework is advantageous for affinity at dopamine and σ receptors. Docking of the C10 analogues at the D3 receptor, suggest that an ionic interaction between the protonated nitrogen atom and Asp110, a H-bond interaction between the C2 phenol and Ser192, a H-bond interaction between the C10 phenol and Cys181 as well as hydrophobic interactions of the aryl rings to Phe106 and Phe345, are critical for high affinity of the compounds.
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Registered trials
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