[Pyrano[3,4-c]quinolines from 1-desaza--oxa-nifedipine].
Pyrano[3,4-c]quinolines from 1-desaza-1-oxa-nifedipine The reaction of the 1,5-diketone 1 with acetic anhydride/acetic acid in the presence of zinc chloride yields the 1-desaza-1-oxa-nifedipine 2 and the annulated lactone 3 as a by-product. The structures of 2 and 3 are confirmed by X-ray structure analysis. The pH-dependent reduction of the nitro group from 2 leads to the pyrano[3,4-c]quinolines 4Aa, b by ring closure. The cyclic hydroxamic acid 4Aa represents a weak, non-selective inhibitor of 5-, 12- and 15-lipoxygenase of human full-blood.
Görlitzer
K
K
Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Trittmacher
J
J
Jones
P G
PG
Frohberg
P
P
Drutkowski
G
G
D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D006801:Humans; D066298:In Vitro Techniques; D007202:Indicators and Reagents; D007975:Leukotriene B4 / Q000096:biosynthesis; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D008958:Models, Molecular; D008968:Molecular Conformation; D009543:Nifedipine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet
D007202:Indicators and Reagents; D016859:Lipoxygenase Inhibitors; D007975:Leukotriene B4; D009543:Nifedipine
Pyrano[3,4-c]chinoline aus 1-Desaza-1-oxa-nifedipin.