cas 98799-37-2, 1-(4-isopropoxy-3-methoxyphenyl)methanamine

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Synthesis and topoisomerase i inhibitory activity of a novel diazaindeno[2,1-b]phenanthrene analogue of Lamellarin D
A novel 5-oxa-6a,8-diazaindeno[2,1-b]phenanthren-7-one scaffold was designed and synthesized as an active analogue of the cytotoxic marine alkaloid Lamellarin D. The design was based on molecular modeling of the site of interaction of Lamellarin D with DNA-topoisomerase I cleavable complex, whereas the synthesis capitalized on a simple Friedel-Crafts cyclization of indole to a β-carbolinone nucleus. The product exhibited topoisomerase I poisoning activity and submicromolar cytotoxicity on human non-small cell lung cancer H460 cell line.
Cananzi, Salvatore,Merlini, Lucio,Artali, Roberto,Beretta, Giovanni Luca,Zaffaroni, Nadia,Dallavalle, Sabrina
experimental part
p. 4971 - 4984
(2011/10/05)

Direct Synthesis of Benzophenanthridines and Benzophenanthridones via SRN1 Reactions
A straightforward and high-yield route to the 11,12-dihydrobenzophenanthridine (3) and 11,12-dihydrobenzophenanthridone (14) ring systems is based upon an SRN1 reaction between 2-halobenzylamines 1 or 2-halobenzoic acids 11 and enolates derived from tetralones 2.The efficient dehydrogenation of 3 or 14 gives the benzophenthridines 4 or benzophenanthridones 15.Use of properly substituted reactants leads to nitidine, avicine, and fagaronine and to analogues of those natural products.
Beugelmans, Rene,Chastanet, Jacqueline,Ginsburg, Helene,Quintero-Cortes, Leticia,Roussi, Georges
p. 4933 - 4938
(2007/10/02)