title: Synthesis of N-diisopropyl phosphoryl benzyltetrahydroisoquinoline, a new class of mitochondrial complexes I and III inhibitors.
abstract: The synthesis of N-(O,O-diisopropylphosphoryl)-benzyltetrahydroisoquinoline (3) has been achieved in a 'one pot' procedure from imine (2) and diisopropyl-phosphorochloridate (1) generated in situ (POCl3 + iPrOH). Compound 3 is the first benzyltetrahydroisoquinoline derivative found to be a potent inhibitor of mitochondrial complexes I and III, and therefore it opens a new perspective with this series of compounds as they can be considered as new class of antitumor agents.
authors.affiliation: Departamento de Farmacología, Farmacognosia y Farmacodinamia, Universidad de Valencia, Burjassot, Spain.
authors.forename: I
authors.initials: I
authors.lastname: Andreu
authors.forename: N
authors.initials: N
authors.lastname: Cabedo
authors.forename: J R
authors.initials: JR
authors.lastname: Tormo
authors.forename: A
authors.initials: A
authors.lastname: Bermejo
authors.forename: R
authors.initials: R
authors.lastname: Mello
authors.forename: D
authors.initials: D
authors.lastname: Cortes
mesh_terms: D000818:Animals; D002417:Cattle; D004579:Electron Transport / Q000187:drug effects; D042967:Electron Transport Complex I; D014450:Electron Transport Complex III / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D008928:Mitochondria / Q000201:enzymology / Q000378:metabolism*; D009247:NADH, NADPH Oxidoreductases / Q000037:antagonists & inhibitors*; D010084:Oxidation-Reduction
chemical_list: D004791:Enzyme Inhibitors; D007546:Isoquinolines; D009247:NADH, NADPH Oxidoreductases; D042967:Electron Transport Complex I; D014450:Electron Transport Complex III