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An alternative synthesis and x-ray crystallographic confirmation of (-)-stepholidine.
Tetrahedron Lett. 2016 May 11;57(19):2090-2092. doi: 10.1016/j.tetlet.2016.03.108.
2
Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity.
Bioorg Med Chem. 2016 May 1;24(9):2060-71. doi: 10.1016/j.bmc.2016.03.037. Epub 2016 Mar 21.
4
Synthesis and evaluation of C9 alkoxy analogues of (-)-stepholidine as dopamine receptor ligands.
Eur J Med Chem. 2017 Jan 5;125:255-268. doi: 10.1016/j.ejmech.2016.09.036. Epub 2016 Sep 14.
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Discovery of Selective Dopamine Receptor Ligands Derived from (-)-Stepholidine via C-3 Alkoxylation and C-3/C-9 Dialkoxylation.
J Med Chem. 2023 Jul 27;66(14):10060-10079. doi: 10.1021/acs.jmedchem.3c00976. Epub 2023 Jul 8.
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Fluoroalkoxylated C-3 and C-9 (S)-12-bromostepholidine analogues with D1R antagonist activity.
Bioorg Chem. 2023 Dec;141:106862. doi: 10.1016/j.bioorg.2023.106862. Epub 2023 Sep 12.
8
(-)-Stepholidine is a potent pan-dopamine receptor antagonist of both G protein- and β-arrestin-mediated signaling.
Psychopharmacology (Berl). 2015 Mar;232(5):917-30. doi: 10.1007/s00213-014-3726-8. Epub 2014 Sep 18.
9
Functional reversal of (-)-Stepholidine analogues by replacement of benzazepine substructure using the ring-expansion strategy.
Chem Biol Drug Des. 2016 Oct;88(4):599-607. doi: 10.1111/cbdd.12796. Epub 2016 Jun 24.
10
Enantioselective total synthesis of (-)-(S)-stepholidine.
J Org Chem. 2009 Dec 4;74(23):9225-8. doi: 10.1021/jo9020826.

引用本文的文献

1
(-)-Stepholidine blocks expression, but not development, of cocaine conditioned place preference in rats.
Neurosci Lett. 2020 Aug 24;734:135151. doi: 10.1016/j.neulet.2020.135151. Epub 2020 Jun 9.
2
Deep Learning in Drug Discovery and Medicine; Scratching the Surface.
Molecules. 2018 Sep 18;23(9):2384. doi: 10.3390/molecules23092384.
3
(-)-Stepholidine reduces cue-induced reinstatement of cocaine seeking and cocaine self-administration in rats.
Drug Alcohol Depend. 2018 Aug 1;189:49-54. doi: 10.1016/j.drugalcdep.2018.04.030. Epub 2018 May 31.

本文引用的文献

1
2,3,9- and 2,3,11-trisubstituted tetrahydroprotoberberines as D2 dopaminergic ligands.
Eur J Med Chem. 2013 Oct;68:150-66. doi: 10.1016/j.ejmech.2013.07.036. Epub 2013 Aug 11.
2
Enantioselective total synthesis of (-)-(S)-stepholidine.
J Org Chem. 2009 Dec 4;74(23):9225-8. doi: 10.1021/jo9020826.
3
An efficient formal synthesis of the human telomerase inhibitor (+/-)-gamma-rubromycin.
Angew Chem Int Ed Engl. 2009;48(43):7996-8000. doi: 10.1002/anie.200903316.
4
The neuropharmacology of (-)-stepholidine and its potential applications.
Curr Neuropharmacol. 2007 Dec;5(4):289-94. doi: 10.2174/157015907782793649.
5
The antipsychotic potential of l-stepholidine--a naturally occurring dopamine receptor D1 agonist and D2 antagonist.
Psychopharmacology (Berl). 2008 Aug;199(2):275-89. doi: 10.1007/s00213-008-1172-1. Epub 2008 Jun 3.
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Synthesis and structure activity relationships of novel non-peptidic metallo-aminopeptidase inhibitors.
Bioorg Med Chem. 2006 Nov 1;14(21):7241-57. doi: 10.1016/j.bmc.2006.06.050. Epub 2006 Jul 17.
7
The dopamine D1 receptor agonist and D2 receptor antagonist LEK-8829 attenuates reinstatement of cocaine-seeking in rats.
Naunyn Schmiedebergs Arch Pharmacol. 2004 Jun;369(6):576-82. doi: 10.1007/s00210-004-0937-2. Epub 2004 May 7.
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Convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids.
Chem Pharm Bull (Tokyo). 2000 Mar;48(3):399-404. doi: 10.1248/cpb.48.399.

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