{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"omics_type":["Unknown"],"volume":["9(8)"],"submitter":["Gao D"],"funding":["Deutsche Forschungsgemeinschaft"],"pubmed_abstract":["The activity of pharmacologically active compounds can be increased by presenting a drug in a defined conformation, which fits exactly into the binding pocket of its target. Herein, the piperazine scaffold was conformationally restricted by substituted C<sub>2</sub>- or C<sub>3</sub>-bridges across the 2- and 6-position. At first, a three-step, one-pot procedure was developed to obtain reproducibly piperazine-2,6-diones with various substituents at the N-atoms in high yields. Three strategies for bridging of piperazine-2,6-diones were pursued: 1. The bicyclic mixed ketals 8-benzyl-6-ethoxy-3-(4-methoxybenzyl)-6-(trimethylsilyloxy)-3,8-diazabicyclo[3.2.1]octane-2,4-diones were prepared by Dieckmann analogous cyclization of 2-(3,5-dioxopiperazin-2-yl)acetates. 2. Stepwise allylation, hydrobo"],"journal":["ChemistryOpen"],"pagination":["874-889"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC7450790"],"repository":["biostudies-literature"],"pubmed_title":["Rigid Scaffolds: Synthesis of 2,6-Bridged Piperazines with Functional Groups in all three Bridges."],"pmcid":["PMC7450790"],"pubmed_authors":["Penno C","Wunsch B","Gao D"],"additional_accession":[]},"is_claimable":false,"name":"Rigid Scaffolds: Synthesis of 2,6-Bridged Piperazines with Functional Groups in all three Bridges.","description":"The activity of pharmacologically active compounds can be increased by presenting a drug in a defined conformation, which fits exactly into the binding pocket of its target. Herein, the piperazine scaffold was conformationally restricted by substituted C<sub>2</sub>- or C<sub>3</sub>-bridges across the 2- and 6-position. At first, a three-step, one-pot procedure was developed to obtain reproducibly piperazine-2,6-diones with various substituents at the N-atoms in high yields. Three strategies for bridging of piperazine-2,6-diones were pursued: 1. The bicyclic mixed ketals 8-benzyl-6-ethoxy-3-(4-methoxybenzyl)-6-(trimethylsilyloxy)-3,8-diazabicyclo[3.2.1]octane-2,4-diones were prepared by Dieckmann analogous cyclization of 2-(3,5-dioxopiperazin-2-yl)acetates. 2. Stepwise allylation, hydrobo","dates":{"release":"2020-01-01T00:00:00Z","publication":"2020 Aug","modification":"2026-07-15T20:40:44.104Z","creation":"2025-05-29T21:27:31.479Z"},"accession":"S-EPMC7450790","cross_references":{"pubmed":["32884883"],"doi":["10.1002/open.202000188"]}}