Molecules 2013, 18(3), 2518-2527; doi:10.3390/molecules18032518
Article

A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin

Received: 21 January 2013; in revised form: 31 January 2013 / Accepted: 7 February 2013 / Published: 26 February 2013
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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 12ae and 1,2-diaza-1,3-diene (DD) 13. Derivatives 10a,ce, 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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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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