6533b832fe1ef96bd129a5b6
RESEARCH PRODUCT
A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin
Gianfranco FaviVirginia SpanòCristina CianciminoBarbara ParrinoAnna CarboneOrazio A. Attanasisubject
IndolesStereochemistryPharmaceutical ScienceAntineoplastic AgentsModerate activityArticleAnalytical Chemistrylcsh:QD241-441Alkaloidslcsh:Organic chemistrytopsentin; bis-indole alkaloids; antitumor activity; ethyl 1-[(<i>tert</i>-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1<i>H</i>-indol-3-yl)-4-[(1-methyl-1<i>H</i>-indol-3-yl)-carbonyl]-1<i>H</i>-pyrrole-3-carboxylatesCell Line Tumortopsentin; bis-indole alkaloids; antitumor activity; ethyl 1-[(tertbutoxycarbonyl) amino]-2-methyl-5-(1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl)- carbonyl]-1H-pyrrole-3-carboxylatesDrug DiscoverymedicineHumansantitumor activityethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl)-carbonyl]-1H-pyrrole-3-carboxylatesPhysical and Theoretical ChemistryAntitumor activityethyl 1-[(tertbutoxycarbonyl) amino]-2-methyl-5-(1-methyl-1H-indol-3-yl)-4-[(1-methyl-1H-indol-3-yl)- carbonyl]-1H-pyrrole-3-carboxylatesChemistryAlkaloidOrganic ChemistryImidazolesCancermedicine.diseaseSettore CHIM/08 - Chimica FarmaceuticaIn vitroHuman tumorbis-indole alkaloidsChemistry (miscellaneous)Cell culturebis-indole alkaloidMolecular MedicineNon small cellDrug Screening Assays Antitumortopsentindescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2013-02-26 | Molecules; Volume 18; Issue 3; Pages: 2518-2527 |