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.

Carbone, A., Spanò, V., Parrino, B., Ciancimino, C., Attanasi, O.A., Favi, G. (2013). A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin. MOLECULES, 18, 2518-2527 [doi:10.3390/molecules18032518].

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

CARBONE, Anna;SPANO', Virginia;PARRINO, Barbara;CIANCIMINO, Cristina;
2013-01-01

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.
Settore CHIM/08 - Chimica Farmaceutica
Carbone, A., Spanò, V., Parrino, B., Ciancimino, C., Attanasi, O.A., Favi, G. (2013). A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin. MOLECULES, 18, 2518-2527 [doi:10.3390/molecules18032518].
File in questo prodotto:
File Dimensione Formato  
molecules 2013.pdf

Solo gestori archvio

Descrizione: main article
Dimensione 212.41 kB
Formato Adobe PDF
212.41 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/72203
Citazioni
  • ???jsp.display-item.citation.pmc??? 2
  • Scopus 15
  • ???jsp.display-item.citation.isi??? 16
social impact