Year: 2013
Type: article
Abstract: Oxazolidinones are known as a new class of antibacterial agents.In our group, the 4,5-disubstituted oxazolidinones have been previously identified to exhibit high affinity for the T box antiterminator transcription system.Among those compounds, ANB-22 and ANB-40 emerged to be the lead compounds showing good RNA-binding activity with high affinity and specificity.In medicinal chemistry, conformationally constraining molecules is a useful approach to optimize the biological activities of drug candidates.This dissertation is devoted to the design and synthesis of the fused tricyclic piperazine analogues and tricyclic triazole analogues of ANB-22 and ANB-40.By employing the aziridine-ring-opening and the Mitsunobu reaction, a series of fused bicyclic and tricyclic oxazolidinone-piperazine derivatives have been prepared.Using similar synthetic strategy and subsequent structural modification, the fused tricyclic piperazine analogues of ANB-22/40 have been successfully obtained as well.The application of the intramolecular azide-alkyne cycloaddition leads to the tricyclic fused oxazolidinone-piperazine-triazole compounds.After appropriate structural modification, the triazole analogues of ANB-22/40 have been prepared.By hydrolyzing the oxazolidinone ring of these tricyclic compounds, a series of amino alcohol derivatives with a piperazine-triazole framework have been generated.In addition, the use of copper
Author: Fang Fang
Institution: Ohio University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W2519341891