23876-39-3Relevant articles and documents
Synthesis and antiprotozoal evaluation of benzothiazolopyrroloquinoxalinones, analogues of kuanoniamine A
Tapia, Ricardo A.,Prieto, Yolanda,Pautet, Felix,Walchshofer, Nadia,Fillion, Houda,Fenet, Bernard,Sarciron, Marie-Elizabeth
, p. 3407 - 3412 (2003)
Boc-aminoethylindoloquinone 8, a key intermediate for the building of pentacyclic quinoneimines, analogues of kuanoniamine A, was synthesized by alkylation of 4,7-dimethoxyindole 3 with 1,2-dibromoethane followed by transformation into azide, reduction of the latter with trimethylphosphine in the presence of 2-(tert-butoxycarbonyloximino)-2-phenylacetonitrile and oxydative demethylation of the Boc-amine 6 with silver(II) oxide. Quinone 8 was then treated in situ with the thiazole o-quinodimethane 10 to afford a regioisomeric mixture of the tetracyclic quinones 11. Treatment of the mixture with trifluoroacetic acid and molecular sieves 4-A provided the corresponding quinoneimines 12. Separation of the regioisomers was performed by preparative thin-layer chromatography on silica gel. The structural assignment was made by 2D 1H-13C HMBC correlations performed on the less polar regioisomer 12b. In vitro anti-leishmanial assays showed that the tested compounds possess a good potency towards two Leishmania sp. as well as against a virulent strain of Toxoplasma gondii and without any cytotoxicity against THP-1 cells.
Synthesis and cytotoxic activity of 2-acyl-1H-indole-4,7-diones on human cancer cell lines
Mahboobi, Siavosh,Sellmer, Andreas,Eichhorn, Emerich,Beckers, Thomas,Fiebig, Heinz-Herbert,Kelter, Gerhard
, p. 85 - 92 (2007/10/03)
Synthesis and cytotoxic activity of a series of 2-acyl-1H-indole-4,7-diones on human cancer cell lines are described. Due to close structural relationship to 2-acylindoles, potent inhibitors of tubulin polymerization, the mode of action of these novel com
Synthesis of novel pentacyclic pyrrolothiazolobenzoquinolinones, analogs of natural marine alkaloids
Bénéteau, Valérie,Besson, Thierry
, p. 2673 - 2676 (2007/10/03)
Multistep synthesis (12 steps) of new pentacyclic compounds, which are structurally very close to natural marine alkaloids, was performed via a Diels-Alder reaction between 4-methylene-5-(bromomethylene)-4,5-dihydrothiazole and a protected dioxotryptamine