dc.creator | Saiz, Cecilia | |
dc.creator | Villamil, Valentina | |
dc.creator | Gonzalez, Mariano Martin | |
dc.creator | Rossi, María Agustina | |
dc.creator | Martínez, Lorena | |
dc.creator | Suescun, Leopoldo | |
dc.creator | Vila, Alejandro Jose | |
dc.creator | Mahler, Graciela | |
dc.date.accessioned | 2018-06-27T18:59:45Z | |
dc.date.available | 2018-06-27T18:59:45Z | |
dc.date.created | 2018-06-27T18:59:45Z | |
dc.date.issued | 2017-01 | |
dc.identifier | Saiz, Cecilia; Villamil, Valentina; Gonzalez, Mariano Martin; Rossi, María Agustina; Martínez, Lorena; et al.; Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 28; 1; 1-2017; 110-117 | |
dc.identifier | 0957-4166 | |
dc.identifier | http://hdl.handle.net/11336/50288 | |
dc.identifier | CONICET Digital | |
dc.identifier | CONICET | |
dc.description.abstract | The synthesis of new oxazolidinylthiazolidines bicycles, oxygen analogues of bisthiazolidines, also known as metallo-β-lactamase inhibitors is described. The reaction of β-aminoalcohols and 2,5-dihydroxy-1,4-dithiane led to oxazolidinylthiazolidines and/or dithioazabicycles as the main products. The distribution pattern depends mainly on the aminoalcohol substituents. In a one-pot reaction, four new bonds are formed in good yields and with high atom efficiency. When the oxazolidinylthiazolidines are formed, two stereogenic centres are generated with high enantiospecificity. The reaction mechanism is discussed based on crystallographic data and interconversion studies. Two oxazolidinylthiazolidines were evaluated as inhibitors of the potent lactamase NDM-1 and compound 4f displayed competitive inhibition with Ki = 1.6 ± 0.6 μM. | |
dc.language | eng | |
dc.publisher | Pergamon-Elsevier Science Ltd | |
dc.relation | info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.tetasy.2016.11.002 | |
dc.relation | info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0957416616302774 | |
dc.relation | info:eu-repo/semantics/altIdentifier/url/https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5451161/ | |
dc.rights | https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ | |
dc.rights | info:eu-repo/semantics/openAccess | |
dc.subject | Synthesis | |
dc.subject | Oxazolidinylthiazolidines Bicycles | |
dc.subject | Inhibitors | |
dc.subject | Ndm-1 | |
dc.title | Enantioselective synthesis of new oxazolidinylthiazolidines as enzyme inhibitors | |
dc.type | info:eu-repo/semantics/article | |
dc.type | info:ar-repo/semantics/artículo | |
dc.type | info:eu-repo/semantics/publishedVersion | |