Several novel racemic aminotetralin derivatives have been prepared using a stereoselective aziridine ring opening reactions and were evaluated for their micro-opioid receptor binding affinity. Selectivity index towards other opioid receptors and antinociceptive activity in mice have been evaluated for the most potent derivatives.
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Visible Light-Mediated [4+2] Annulation of Silylimines with Olefins to 1-Aminotetralins Enabled by Diradical Hydrogen Atom Transfer of C-H Bonds.
Angew Chem Int Ed Engl
November 2024
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing, 401331, P. R. China.
A facile photochemical, one-pot synthesis of highly functionalized 1-aminotetralins derivatives (>70 examples) from readily accessible o-alkyl and o-formyl aryl silylimines with olefins is described. A diradical-mediated hydrogen atom transfer (DHAT) of primary, secondary, and tertiary C(sp)-H bonds of o-alkyl arylsilylimines and C(sp)-H bonds of o-formyl arylsilylimines enabled a [4+2] annulation with olefins in excellent diastereoselectivity. This was accomplished upon irradiation at λ = 420 nm in the presence of thioxanthen-9-one (10 mol %) as the sensitizer via energy transfer.
View Article and Find Full Text PDFDivergent Synthesis of Multi-Substituted Aminotetralins via [4+2] Annulation of Aldimines with Alkenes by Rare-Earth-Catalyzed Benzylic C(sp )-H Activation.
Angew Chem Int Ed Engl
March 2024
Advanced Catalysis Research Group, RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan.
The search for efficient and selective methods for the divergent synthesis of multi-substituted aminotetralins is of much interest and importance. We report herein for the first time the diastereoselective [4+2] annulation of 2-methyl aromatic aldimines with alkenes via benzylic C(sp )-H activation by half-sandwich rare-earth catalysts, which constitutes an efficient route for the divergent synthesis of both trans and cis diastereoisomers of multi-substituted 1-aminotetralin derivatives from readily accessible aldimines and alkenes. The use of a scandium catalyst bearing a sterically demanding cyclopentadienyl ligand such as C Me SiMe or C Me exclusively afforded the trans-selective annulation products in the reaction of aldimines with styrenes and aliphatic alkenes.
View Article and Find Full Text PDFThe evaluation of N-propargylamine-2-aminotetralin as an inhibitor of monoamine oxidase.
Bioorg Med Chem Lett
July 2022
Centre of Excellence for Pharmaceutical Sciences, North-West University, Potchefstroom 2520, South Africa; Pharmaceutical Chemistry, School of Pharmacy, North-West University, Potchefstroom 2520, South Africa. Electronic address:
Monoamine oxidase B (MAO-B) inhibitors are established therapy for Parkinson's disease and act, in part, by blocking the MAO-catalysed metabolism of dopamine in the brain. Two propargylamine-containing MAO-B inhibitors, selegiline [(R)-deprenyl] and rasagiline, are currently used in the clinic for this purpose. These compounds are mechanism-based inactivators and, after oxidative activation, form covalent adducts with the FAD co-factor.
View Article and Find Full Text PDFSynthesis of Pharmaceutically Relevant 2-Aminotetralin and 3-Aminochroman Derivatives via Enzymatic Reductive Amination.
Angew Chem Int Ed Engl
November 2021
Department of Chemistry, University of Manchester, Manchester Institute of Biotechnology, 131 Princess Street, Manchester, M1 7DN, UK.
2-Aminotetralin and 3-aminochroman derivatives are key structural motifs present in a wide range of pharmaceutically important molecules. Herein, we report an effective biocatalytic approach towards these molecules through the enantioselective reductive coupling of 2-tetralones and 3-chromanones with a diverse range of primary amine partners. Metagenomic imine reductases (IREDs) were employed as the biocatalysts, obtaining high yields and enantiocomplementary selectivity for >15 examples at preparative scale, including the precursors to Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT.
View Article and Find Full Text PDFDopamine D Receptor Agonist Binding Kinetics-Role of a Conserved Serine Residue.
Int J Mol Sci
April 2021
Department of Neuroscience, Karolinska Institutet, 171 77 Stockholm, Sweden.
The forward (k) and reverse (k) rate constants of drug-target interactions have important implications for therapeutic efficacy. Hence, time-resolved assays capable of measuring these binding rate constants may be informative to drug discovery efforts. Here, we used an ion channel activation assay to estimate the ks and ks of four dopamine D receptor (DR) agonists; dopamine (DA), p-tyramine, (R)- and (S)-5-OH-dipropylaminotetralin (DPAT).
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