1-(2′-Bromobenzyl)-6,7-dihydroxy-N-methyl-tetrahydroisoquinoline and 1,2-Demethyl-nuciferine as Agonists in Human D2 Dopamine Receptors

Journal of Natural Products
2020.0

Abstract

Certain D(2)-like dopamine receptor (DR) agonists are useful therapeutically as antiparkinsonian drugs, whereas D(2)-like DR antagonists or partial agonists are proven effective as antipsychotics. Two isoquinoline derivatives, 1-(2'-bromobenzyl)-6,7-dihydroxy-N-methyl-tetrahydroisoquinoline (Br-BTHIQ, 1) and 1,2-demethyl-nuciferine (aporphine, 2), were herein synthesized, and their dopaminergic affinity in cloned human D(2)R, D(3)R, and D(4)R subtypes and their behavior as agonists/antagonists were evaluated. They showed affinity values (K(i)) for hD(2), hD(3), and hD(4) DR within the nanomolar range. The trends in affinity were hD(4)R >> hD(3)R > hD(2)R for Br-BTHIQ (1) and hD(2)R > hD(4)R > hD(3)R for 1,2-demethyl-nuciferine (2). The functional assays of cyclic adenosine monophosphate signaling at human D(2)R showed a partial agonist effect for Br-BTHIQ (1) and full agonist behavior for aporphine (2), with half maximal effective concentration values of 2.95 and 10.2 muM, respectively. Therefore, both isoquinolines 1 and 2 have emerged as lead molecules for the synthesis of new therapeutic drugs that ultimately may be useful to prevent schizophrenia and Parkinson's disease, respectively.

Knowledge Graph

Similar Paper

1-(2′-Bromobenzyl)-6,7-dihydroxy-N-methyl-tetrahydroisoquinoline and 1,2-Demethyl-nuciferine as Agonists in Human D<sub>2</sub> Dopamine Receptors
Journal of Natural Products 2020.0
3,4-Dihydroxy- and 3,4-methylenedioxy- phenanthrene-type alkaloids with high selectivity for D2 dopamine receptor
Bioorganic &amp; Medicinal Chemistry Letters 2013.0
Dopaminergic isoquinolines with hexahydrocyclopenta[ ij ]-isoquinolines as D 2 -like selective ligands
European Journal of Medicinal Chemistry 2016.0
Synthesis and pharmacological characterization of 1-phenyl-, 4-phenyl-, and 1-benzyl-1,2,3,4-tetrahydroisoquinolines as dopamine receptor ligands
Journal of Medicinal Chemistry 1988.0
Synthesis and evaluation of 1,2,3,4-tetrahydro[1]benzothieno[2,3-h]isoquinolines as dopamine antagonists
Journal of Medicinal Chemistry 1981.0
Tetrahydroisoquinolines as dopaminergic ligands: 1-Butyl-7-chloro-6-hydroxy-tetrahydroisoquinoline, a new compound with antidepressant-like activity in mice
Bioorganic &amp; Medicinal Chemistry 2009.0
Synthesis and dopaminergic activity of a series of new 1-aryl tetrahydroisoquinolines and 2-substituted 1-aryl-3-tetrahydrobenzazepines
Bioorganic Chemistry 2018.0
Aporphines. 21. Dopaminergic activity of aporphine and benzylisoquinoline derivatives. Synthesis of 8-hydroxyaporphines and 1-(hydroxybenzyl)-2-n-propyl-1,2,3,4-tetrahydroisoquinolines
Journal of Medicinal Chemistry 1977.0
Synthesis and SAR study of a novel series of dopamine receptor agonists
Bioorganic &amp; Medicinal Chemistry 2014.0
Mammalian alkaloids. 8. Synthesis and biological effects of tetrahydropapaveroline related 1-benzyltetrahydroisoquinolines
Journal of Medicinal Chemistry 1980.0