2026-05-30T20:27:35Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/45432022-12-19T11:19:05Zcom_10259_3924com_10259_5086com_10259_2604com_10259_4354col_10259_3925col_10259_4355

Reversal of diastereoselectivity in the synthesis of Peptidomimetic 3‑Carboxamide-1,4-benzodiazepin-5-ones Pertejo Fernández, Pablo Corres, Nazaret Torroba Pérez, Tomás García Valverde, María Chemistry, Organic Química orgánica Enantiopure 3-carboxamide-1,4-benzodiazepin-5-ones were synthesized via the Ugi reaction followed by the Staudinger/aza-Wittig or reduction reactions in only two steps. A complete reversal of diastereoselectivity was achieved depending on the cyclization methodology employed. The different orientation of the C3 substituent in our 3-substituted 1,4-benzodiazepin-5-ones with respect to the most studied 1,4-benzodiazepin-2-ones makes them complementary in the development of new drugs because the primary source of binding selectivity of 1,4-benzodiazepines is the selective recognition of ligand conformations by the receptor. Ministerio de Economía y Competitividad, Spain (Project CTQ2012-31611), Junta de Castilla y León, Consejería de Educación y Cultura y Fondo Social Europeo (Project BU246A12-1) and the European Commission, Seventh Framework Programme (Project SNIFFER FP7-SEC-2012-312411). 2017-07-27T11:07:43Z 2017-07-27T11:07:43Z 2015-02-06 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1523-7060 http://hdl.handle.net/10259/4543 10.1021/ol503628r eng Organic Letters. 2015, V. 17, n. 3, p. 612–615 http://dx.doi.org/10.1021/ol503628r info:eu-repo/grantAgreement/EC/FP7/312411 info:eu-repo/semantics/openAccess application/pdf American Chemical Society