Synthesis and absolute configuration of cyclic synthetic cathinones derived from α-tetralone

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F24%3A43929123" target="_blank" >RIV/60461373:22310/24:43929123 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60461373:22330/24:43929123 RIV/60461373:22340/24:43929123 RIV/00023752:_____/24:43921324

Výsledek na webu

<a href="https://onlinelibrary.wiley.com/doi/full/10.1002/chir.23646" target="_blank" >https://onlinelibrary.wiley.com/doi/full/10.1002/chir.23646</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/chir.23646" target="_blank" >10.1002/chir.23646</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and absolute configuration of cyclic synthetic cathinones derived from α-tetralone

Popis výsledku v původním jazyce

The emergence of new synthetic cathinones continues to be a matter of public health concern. In fact, already known products (drugs) are being rapidly replaced by new structurally related alternatives, whereby modifications in the basic cathinone structure are used by manufacturers to circumvent the legislation. On the other hand, some derivatives of synthetic cathinones represent important pharmaceuticals with antidepressant properties. In the search for pharmaceutically relevant analogs, the main goal of the present study was to design and characterize novel cyclic α-tetralone-based derivatives of synthetic cathinones. We synthesized a series of derivatives and verified their chemical structure. Subsequently, chiral separation has been accomplished by high-performance liquid chromatography (HPLC) equipped with a circular dichroism (CD) detector, which directly provided CD spectra of the enantiomers of the analyzed substances at 252 nm. Using density functional theory calculations, we have obtained stable conformers of selected enantiomers in solution and their relative abundances, which we used to simulate their spectra. The experimental and calculated data have been used to assign the absolute configuration of six as-yet unknown synthetic cathinones. © 2024 The Authors. Chirality published by Wiley Periodicals LLC.

Název v anglickém jazyce

Synthesis and absolute configuration of cyclic synthetic cathinones derived from α-tetralone

Popis výsledku anglicky

The emergence of new synthetic cathinones continues to be a matter of public health concern. In fact, already known products (drugs) are being rapidly replaced by new structurally related alternatives, whereby modifications in the basic cathinone structure are used by manufacturers to circumvent the legislation. On the other hand, some derivatives of synthetic cathinones represent important pharmaceuticals with antidepressant properties. In the search for pharmaceutically relevant analogs, the main goal of the present study was to design and characterize novel cyclic α-tetralone-based derivatives of synthetic cathinones. We synthesized a series of derivatives and verified their chemical structure. Subsequently, chiral separation has been accomplished by high-performance liquid chromatography (HPLC) equipped with a circular dichroism (CD) detector, which directly provided CD spectra of the enantiomers of the analyzed substances at 252 nm. Using density functional theory calculations, we have obtained stable conformers of selected enantiomers in solution and their relative abundances, which we used to simulate their spectra. The experimental and calculated data have been used to assign the absolute configuration of six as-yet unknown synthetic cathinones. © 2024 The Authors. Chirality published by Wiley Periodicals LLC.

Druh

J_SC - Článek v periodiku v databázi SCOPUS

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2024

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

CHIRALITY

ISSN

0899-0042

e-ISSN

—

Svazek periodika

36

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

ZA - Jihoafrická republika

Počet stran výsledku

11

Strana od-do

"e23646"

Kód UT WoS článku

—

EID výsledku v databázi Scopus

2-s2.0-85185097393