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[Pyrano[3,4-c]quinolines from 1-desaza--oxa-nifedipine]
K Görlitzer1, J Trittmacher, P G Jones
1Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Germany. k.goerlitzer@tu-bs.de
Die Pharmazie
|September 12, 2003
Abstract:
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.