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A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin
Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy
Dipartimento di Scienze Biomolecolari, Università degli Studi di Urbino "Carlo Bo", Via I Maggetti 24, 61029 Urbino, Italy
* Authors to whom correspondence should be addressed.
Received: 21 January 2013; in revised form: 31 January 2013 / Accepted: 7 February 2013 / Published: 26 February 2013
Abstract: A series of substituted ethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5- (1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl)carbonyl]-1H-pyrrole-3-carboxylates were prepared in excellent yields (82-98%) by one-pot reactions between β-dicarbonyl compounds 12a–e and 1,2-diaza-1,3-diene (DD) 13. Derivatives 10a,c–e, deazaanalogues of the bis-indole alkaloid topsentin, screened by the National Cancer Institute (Bethesda, MD, USA) in the in vitro one dose primary anticancer assay against a panel of about 60 human tumor cell lines, showed no significant activity, with the exception of compound 9e, which showed moderate activity against the HOP-92 cell line of the non small cell lung cancer sub-panel and the SNB-75 cell line of the CNS sub-panel.
Keywords: topsentin; bis-indole alkaloids; antitumor activity; ethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl)-carbonyl]-1H-pyrrole-3-carboxylates
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Carbone, A.; Spanò, V.; Parrino, B.; Ciancimino, C.; Attanasi, O.A.; Favi, G. A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin. Molecules 2013, 18, 2518-2527.
Carbone A, Spanò V, Parrino B, Ciancimino C, Attanasi OA, Favi G. A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin. Molecules. 2013; 18(3):2518-2527.
Carbone, Anna; Spanò, Virginia; Parrino, Barbara; Ciancimino, Cristina; Attanasi, Orazio A.; Favi, Gianfranco. 2013. "A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin." Molecules 18, no. 3: 2518-2527.