Fused Ring Molecular Scaffold with 3D Architecture for Constrained Peptidomimetics: Polymer-Supported Stereoselective Synthesis of Tetrahydrobenzo[e]pyrazino[2,1-c][1,2,4]thiadiazinone 6,6-dioxide via N-Acyl Iminiums.
3,4,4a,5-Tetrahydrobenzo[e]pyrazino[2,1-c][1,2,4]thiadiazin-1(2H)-one 6,6-dioxides, molecular scaffolds with 3D architecture, were synthesized on solid supports via tandem N-acyl iminium ion cyclization followed by nucleophilic addition. The modular synthesis proceeded under mild conditions using commercially available building blocks and provided crude products with respectable purity. The synthesized compounds are applicable as fused nitrogenous heterocyclic compounds in drug discovery and as constrained peptidomimetics incorporated into a peptide backbone.
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
Eva
E
Schütznerová
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
Pedro
P
Verdía
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.|Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame , Notre Dame, Indiana 46556, United States.
Viktor
V
Krchňák
D003499:Cyclic S-Oxides / Q000138:chemical synthesis*; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007097:Imines / Q000138:chemical synthesis*; D010455:Peptides / Q000737:chemistry; D057786:Peptidomimetics / Q000138:chemical synthesis*; D011108:Polymers / Q000737:chemistry*; D013237:Stereoisomerism
D003499:Cyclic S-Oxides; D006575:Heterocyclic Compounds, 3-Ring; D007097:Imines; D010455:Peptides; D057786:Peptidomimetics; D011108:Polymers
3D architecture; drug discovery; modular synthesis; molecular scaffolds; peptidomimetics; solid supports