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?-Amino- and Alkoxy-Substituted Disilanides.

ABSTRACT: Our recent study on formal halide adducts of disilenes led to the investigation of the synthesis and properties of ?-fluoro- and chlorodisilanides. The reaction of the functionalized neopentasilanes (Me3Si)3SiSiPh2NEt2 and (Me3Si)3SiSiMe2OMe with KOtBu in the presence of 18-crown-6 provided access to structurally related ?-alkoxy- and amino-substituted disilanides. The obtained Et2NPh2Si(Me3Si)2SiK·18-crown-6 was converted to a magnesium silanide and further on to Et2NPh2Si(Me3Si)2Si-substituted ziroconocene and hafnocene chlorides. In addition, an example of a silanide containing both Et2NPh2Si and FPh2Si groups was prepared with moderate selectivity. Also, the analogous germanide Et2NPh2Si(Me3Si)2GeK·18-crown-6 could be obtained.

SUBMITTER: Balatoni I

PROVIDER: S-EPMC6864825 | biostudies-literature | 2019 Oct

REPOSITORIES: biostudies-literature

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β-Amino- and Alkoxy-Substituted Disilanides.

Balatoni Istvan I Hlina Johann J Zitz Rainer R Pöcheim Alexander A Baumgartner Judith J Marschner Christoph C

Molecules (Basel, Switzerland) 20191023 21

Our recent study on formal halide adducts of disilenes led to the investigation of the synthesis and properties of β-fluoro- and chlorodisilanides. The reaction of the functionalized neopentasilanes (Me3Si)3SiSiPh2NEt2 and (Me3Si)3SiSiMe2OMe with KOtBu in the presence of 18-crown-6 provided access to structurally related β-alkoxy- and amino-substituted disilanides. The obtained Et2NPh2< ...[more]

PMID: 31652810

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Project description:Background: 2,4,5-Trimethoxyamphetamine (TMA-2) is a potent psychedelic compound. Structurally related 4-alkyloxy-substituted 2,5-dimethoxyamphetamines and phenethylamine congeners (2C-O derivatives) have been described but their pharmacology is mostly undefined. Therefore, we examined receptor binding and activation profiles of these derivatives at monoamine receptors and transporters. Methods: Receptor binding affinities were determined at the serotonergic 5-HT1A, 5-HT2A, and 5-HT2C receptors, trace amine-associated receptor 1 (TAAR1), adrenergic ?1 and ?2 receptors, dopaminergic D2 receptor, and at monoamine transporters, using target-transfected cells. Additionally, activation of 5-HT2A and 5-HT2B receptors and TAAR1 was determined. Furthermore, we assessed monoamine transporter inhibition. Results: Both the phenethylamine and amphetamine derivatives (K i = 8-1700 nM and 61-4400 nM, respectively) bound with moderate to high affinities to the 5-HT2A receptor with preference over the 5-HT1A and 5-HT2C receptors (5-HT2A/5-HT1A = 1.4-333 and 5-HT2A/5-HT2C = 2.1-14, respectively). Extending the 4-alkoxy-group generally increased binding affinities at 5-HT2A and 5-HT2C receptors but showed mixed effects in terms of activation potency and efficacy at these receptors. Introduction of a terminal fluorine atom into the 4-ethoxy substituent by trend decreased, and with progressive fluorination increased affinities at the 5-HT2A and 5-HT2C receptors. Little or no effect was observed at the 5-HT1A receptor for any of the substances tested (K i ? 2700 nM). Phenethylamines bound more strongly to the TAAR1 (K i = 21-3300 nM) compared with their amphetamine analogs (K i = 630-3100 nM). Conclusion: As seen with earlier series investigated, the 4-alkyloxy-substituted 2,5-dimethoxyamphetamines and phenethylamines share some trends with the many other phenethylamine pharmacophore containing compounds, such as when increasing the size of the 4-substituent and increasing the lipophilicity, the affinities at the 5-HT2A/C subtype also increase, and only weak 5-HT2A/C subtype selectivities were achieved. At least from the binding data available (i.e., high affinity binding at the 5-HT2A receptor) one may predict mainly psychedelic-like effects in humans, at least for some of the compound investigated herein.

Dataset Information

?-Amino- and Alkoxy-Substituted Disilanides.

Publications

β-Amino- and Alkoxy-Substituted Disilanides.

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