Eine zweistufige Synthese von cytostatisch wirksamen Benzo[c]phenanthridin-Derivaten

Abstract

Große Mengen zugänglich: Beschrieben wird eine kurze Synthese von Benzo[c]phenanthridin‐Derivaten durch Umsetzung von Aldehyden und 2‐Methylbenzonitril in Gegenwart von Kalium‐tert‐butanolat und anschließende Dehydrierung (siehe Schema). Die Verbindungen zeigen zum Teil ausgezeichnete cytostatische Aktivitäten, und es besteht die Möglichkeit, Substituenten direkt in das Grundgerüst einzuführen.

Palladium‐Catalyzed Synthesis of Phenanthridine/Benzoxazine‐Fused Quinazolinones by Intramolecular CH Bond Activation

“…[15] Phenanthridine structural motifs representa nother class of biologically relevantc ompounds with extensive pharmacological activities and applications. [16] Important compounds in this class include ethidium salts as DNA intercalators, [17] fagaronine, [18] and trispheridine, which display excellent antiproliferative effects on both human and mousec ell lines (Figure1). [19] Phenanthridine derivatives have also shown promise as radiotracers for imaging of brain 5-HT 4 receptors by single photon emission computedtomography.…”

“…Therefore, different bases including K 2 CO 3 ,C s 2 CO 3 ,K OAc, NaOAc, CsOAc, NaHCO 3 ,K 3 PO 4 ,a nd Et 3 N were examined (Table 1, entries 9-16) and, of these, Na 2 CO 3 was found to be the most effective. Having optimised the base and the catalyst, our next focus was the selectiono fa na ppropriate solvent, whereupon DMF emerged as the optimal choice, after having also performed the reactioninDMSO, toluene, acetonitrile, and water (Table1,e ntries [17][18][19][20]. Another significant observation of the reaction wasadecrease in the yield of the product either with an increasei nt emperature from 100 8Cto1 20 8Coradecrease in temperature to 80 8C.…”