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Open Access Pyrano[3,4-c]chinoline aus 1-Desaza-1-oxa-nifedipin

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Die Umsetzung des 1,5-Diketons 1 mit Acetanhydrid/Eisessig in Gegenwart von Zinkchlorid liefert neben dem 1-Desaza-1-oxa-nifedipin (2) das anellierte Lacton 3. Die Struktur von 2 und 3 wird durch Röntgenkristallanalyse bewiesen. Die pH-abhängige Reduktion der Nitrogruppe von 2 führt unter Ringschluss zu den Pyrano[3,4-c]chinolinen 4Aa, b. Die cyclische Hydroxamsäure 4Aa ist ein schwacher, nicht selektiver Hemmstoff von 5-, 12- und 15-Lipoxygenasen von menschlichem Vollblut.

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.
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Document Type: Research Article

Affiliations: 1: Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Beethovenstr. 55, Braunschweig, 38106, Germany, Email: [email protected] 2: Institut für Pharmazeutische Chemie der Technischen Universität Braunschweig, Braunschweig, Germany 3: Institut für Anorganische und Analytische Chemie der Technischen Universität Braunschweig, Braunschweig, Germany 4: Institut für Pharmazeutische Chemie der Martin-Luther-Universität Halle-Wittenberg, Halle-Wittenberg, Germany

Publication date: August 1, 2003

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