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Chain Extension of Piperazine in Ethanol: Synthesis of 2-(4-(2-(Phenylthio)ethyl)piperazinyl)acetonitriles and ACAT-1 Inhibitors

Authors :
Ying Huang
Tingyu Zhu
Yinghua Li
Deguang Huang
Source :
Molecules, Vol 29, Iss 16, p 3723 (2024)
Publication Year :
2024
Publisher :
MDPI AG, 2024.

Abstract

A base-induced synthesis of 2-(4-(2-(phenylthio)ethyl)piperazinyl) acetonitriles by reaction of disulfides, 1-(chloromethyl)-4-aza-1-azonia bicyclo[2.2.2]octane chloride and trimethylsilyl cyanide is reported. The scope of the method is demonstrated with 30 examples. The reaction mechanism research indicates that the three-component reaction would be a SN2 reaction. The products exhibit good activities towards advanced synthesis of aqueous soluble acyl-CoA: cholesterol O-acyltransferase-1 (ACAT-1) inhibitors. Our work is superior as it uses less-odor disulfides as carbon sources and EtOH as solvent in a water and dioxygen insensitive reaction system, followed by a simple purification process.

Details

Language :
English
ISSN :
14203049
Volume :
29
Issue :
16
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.0e08e3da2646492b936403a61195fd97
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules29163723