title: Double dearomatization of bis(diphenylphosphinamides) through anionic cyclization. A facile route of accessing multifunctional systems with antitumor properties.
abstract: The sequential one-pot double dearomatization of bis(N-benzyl-P,P-diphenylphosphinamides) via anionic cyclization is described for the first time. Protonation and alkylation of the dearomatized dianions provide bis(tetrahydro-2,1-benzazaphospholes) in good yield and with very high regio- and stereocontrol. Acid-catalyzed methanolysis of the bisheterocycles affords bis(methyl gamma-aminophosphinates) stereospecifically. The doubly phosphorylated systems proved to be active against a series of cancer cell lines.
authors: Area de Química Orgánica, Universidad de Almería, Carretera de Sacramento, 04120 Almería, Spain.
authors: Gloria
authors: G
authors: Ruiz-Gómez
authors: María José
authors: MJ
authors: Iglesias
authors: Manuel
authors: M
authors: Serrano-Ruiz
authors: Santiago
authors: S
authors: García-Granda
authors: Andrés
authors: A
authors: Francesch
authors: Fernando
authors: F
authors: López-Ortiz
authors: Carmen
authors: C
authors: Cuevas
mesh_terms: D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity*; D000838:Anions / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D001372:Aza Compounds / Q000737:chemistry; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003500:Cyclization; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010720:Phosphines / Q000737:chemistry*; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides; D000838:Anions; D000970:Antineoplastic Agents; D001372:Aza Compounds; D010720:Phosphines