Next Article in Journal
(Z)-2-{[(4-Chloro-5H-1,2,3-dithiazol-5-ylidene)amino](methylthio)methylene}malononitrile
Previous Article in Journal
In Silico Evaluation of a Promising Key Intermediate Thieno [2,3-d] Pyrimidine Derivative with Expected JAK2 Kinase Inhibitory Activity
Communication

Design, Synthesis and 5-HT1A Binding Affinity of N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine and N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine

1
Department of Pharmacy, Division of Pharmaceutical Chemistry, School of Health Sciences, National and Kapodistrian University of Athens, Panepistimiopolis Zografou, 15771 Athens, Greece
2
BioFarma Research Group, Centro Singular de Investigación en Medicina Molecular y Enfermedades Crónicas (CIMUS), Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain
3
Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari Aldo Moro, Via E. Orabona 4, 70125 Bari, Italy
*
Author to whom correspondence should be addressed.
Academic Editor: Hideto Miyabe
Molbank 2022, 2022(1), M1353; https://doi.org/10.3390/M1353
Received: 22 February 2022 / Revised: 5 March 2022 / Accepted: 7 March 2022 / Published: 10 March 2022
Based on previously highlighted structural features, the development of highly selective 5-HT1A receptor inhibitors is closely linked to the incorporation of a 4-alkyl-1-arylpiperazine scaffold on them. In this paper, we present the synthesis of two new compounds bearing the 2-MeO-Ph-piperazine moiety linked via a three carbon atom linker to the amine group of 1-adamantanamine and memantine, respectively. Both were tested for their binding affinity against 5-HT1A receptor. N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine fumarate (8) and N-(3-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine fumarate (10) proved to be highly selective ligands towards 5-HT1A receptor with a binding constant of 1.2 nM and 21.3 nM, respectively, while 5-carboxamidotriptamine (5-CT) (2) was used as an internal standard for this assay with a measured Ki = 0.5 nM. View Full-Text
Keywords: serotonin receptors; 5-HT1A receptors; arylpiperazine inhibitors; carbocyclic rings; cage-like structures; blood-brain barrier; adamantane derivatives; NMR serotonin receptors; 5-HT1A receptors; arylpiperazine inhibitors; carbocyclic rings; cage-like structures; blood-brain barrier; adamantane derivatives; NMR
Show Figures

Graphical abstract

MDPI and ACS Style

Zoidis, G.; Loza, M.I.; Catto, M. Design, Synthesis and 5-HT1A Binding Affinity of N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine and N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine. Molbank 2022, 2022, M1353. https://doi.org/10.3390/M1353

AMA Style

Zoidis G, Loza MI, Catto M. Design, Synthesis and 5-HT1A Binding Affinity of N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine and N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine. Molbank. 2022; 2022(1):M1353. https://doi.org/10.3390/M1353

Chicago/Turabian Style

Zoidis, Grigoris, María I. Loza, and Marco Catto. 2022. "Design, Synthesis and 5-HT1A Binding Affinity of N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)tricyclo[3.3.1.13,7]decan-1-amine and N-(3-(4-(2-Methoxyphenyl)piperazin-1-yl)propyl)-3,5-dimethyl-tricylo[3.3.1.13,7]decan-1-amine" Molbank 2022, no. 1: M1353. https://doi.org/10.3390/M1353

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop