Ultrasound assisted one-pot synthesis and preliminary in vitro studies of salicylamide arylpiperazines as dual 5-HT1A/5-HT7 ligands
Authors:
- Jolanta Jaśkowska,
- Anna Karolina Drabczyk,
- Paweł Śliwa,
- Przemysław Jodłowski,
- Edyta Pindelska,
- Damian Kułaga,
- Przemysław Zaręba,
- Zbigniew Majka,
- Agata Siwek,
- Małgorzata Wolak,
- Marcin Kołaczkowski
Abstract
In our research to find new dual 5-HT1A/5-HT7 ligands from the long-chain arylpiperazine (LCAP) family, we applied a new synthesis method with the support of ultrasound. The first tests related to the synthesis were carried out on the preparation of approved drugs with arylpiperazine structures such as aripiprazole, trazodone and flibanserin . The results were very satisfactory. In the next stage of the research, we obtained the compounds from the LCAPs group using the sonochemical method, with salicylamide in the structure, a flexible / stiffened linker and a fragment of o-methoxyarylpiperazine / m-chloroarylpiperazine. Among the compounds obtained, two selective 5-HT1A / 5-HT7 ligands were selected, i.e. 2-((4-((4-(2-methoxyphenyl)piperazin-1- yl)methyl)benzyl)oxy)benzamide (18) (5-HT1A Ki = 12.6 nM, 5-HT7 Ki = 6.8 nM) and 2-((4-((4-(3-chlorophenyl)piperazin-1-yl)methyl)benzyl)oxy)benzamide (23) (5-HT1A Ki = 11.6 nM, 5-HT7 Ki = 5.5 nM).
- Record ID
- CUT12329f52f57148f58575e8868de3d094
- Publication categories
- ;
- Author
- Journal series
- Journal of Molecular Structure, ISSN 0022-2860, e-ISSN 1872-8014
- Issue year
- 2023
- Vol
- 1275
- Pages
- [1-12]
- Article number
- 134585
- Other elements of collation
- schem.; tab.; Bibliografia (na s.) - 11-12; Bibliografia (liczba pozycji) - 36; Oznaczenie streszczenia - Abstr.; Data udostępnienia on-line - 2022-11-20; Numeracja w czasopiśmie - Vol. 1275
- Keywords in English
- ultrasound-assisted synthesis, PTC, 5-HT, trazodone, aripiprazole, flibanserin, serotonin receptor ligands, dual 5-HT1A/5-HT7 ligands, in vitro study, molecular modeling
- ASJC Classification
- ; ; ;
- DOI
- DOI:10.1016/j.molstruc.2022.134585 Opening in a new tab
- URL
- https://www.sciencedirect.com/science/article/pii/S002228602202230X Opening in a new tab
- Language
- eng (en) English
- Score (nominal)
- 70
- Score source
- journalList
- Score
- Publication indicators
- Additional fields
- Indeksowana w: Web of Science, Scopus
- Uniform Resource Identifier
- https://cris.pk.edu.pl/info/article/CUT12329f52f57148f58575e8868de3d094/
- URN
urn:pkr-prod:CUT12329f52f57148f58575e8868de3d094
* presented citation count is obtained through Internet information analysis, and it is close to the number calculated by the Publish or PerishOpening in a new tab system.