title: Aziridines from alkenyl-β-D-galactopyranoside derivatives: Stereoselective synthesis and in vitro selective anticancer activity.
abstract: A series of new aziridines β-D-galactopyranoside derivatives were synthesized from alkenyl β-D-galactopyranosides employing Sharpless conditions. The structures of the compounds were established by (1)H NMR, (13)C NMR, MS, HRMS and elemental analysis. The stereoselectivity of the reaction and the structural requirements of the alkenyl precursor for improving diastereoisomeric excesses of the direct aziridination reaction were also studied. The new compounds were subjected to a preliminary screening for cytotoxic activity against human lung cancer cells vs. human non-malignant lung cells. Terminal aziridine derivatives showed activity and, most notably, selectivity. One of the most active and selective compounds was also evaluated against breast cancer cells, melanoma cells, and non-malignant cells from the same origin. Its cytotoxic activity was similar to that of the positive controls, displaying a highly selective cytotoxic activity against both types of cancer cells.
authors.affiliation: Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad de Sevilla, 41071 Sevilla, Spain. Electronic address: vega@us.es.
authors.forename: José M
authors.initials: JM
authors.lastname: Vega-Pérez
authors.forename: Carlos
authors.initials: C
authors.lastname: Palo-Nieto
authors.forename: Margarita
authors.initials: M
authors.lastname: Vega-Holm
authors.forename: Purificación
authors.initials: P
authors.lastname: Góngora-Vargas
authors.forename: José Manuel
authors.initials: JM
authors.lastname: Calderón-Montaño
authors.forename: Estefanía
authors.initials: E
authors.lastname: Burgos-Morón
authors.forename: Miguel
authors.initials: M
authors.lastname: López-Lázaro
authors.forename: Fernando
authors.initials: F
authors.lastname: Iglesias-Guerra
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001388:Aziridines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D005690:Galactose / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D061986:MCF-7 Cells; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000970:Antineoplastic Agents; D001388:Aziridines; D005690:Galactose
keywords: Aziridine carbohydrate derivative; Cancer; Selective cytotoxic activity; Stereoselective synthesis