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  • Title: Synthesis and cytotoxic activity of dimeric analogs of acronycine in the benzo[b]pyrano[3,2-h]acridin-7-one series.
    Author: Gaslonde T, Michel S, Koch M, Pfeiffer B, Léonce S, Pierré A, Tillequin F.
    Journal: Chem Pharm Bull (Tokyo); 2007 May; 55(5):734-8. PubMed ID: 17473459.
    Abstract:
    Coupling of 6-hydroxy-3,3-14-trimethyl-3,14-dihydro-7H-benzo[b]pyrano[3,2-h]acridin-7-one (6) with alpha,omega-diiodoalkanes of varying length under alkaline conditions gave dimers 7-10. Halogenated ethers 11-14, cyclization products 15-17, and compounds 18-22 were also isolated in small yield from the reaction mixtures. Compounds 7-10 were more potent than acronycine and benzo[b]acronycine in inhibiting L1210 cell proliferation. The length of the alkyl ether linkage between the two benzopyranoacridone units had a dramatic influence on the cytotoxic activity. Compound 9 (n=5) was the most active, with an IC(50) value against L1210 cells within the same range of magnitude as diacetate 5, currently under clinical development.
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