ChemInform Abstract: New Synthetic Approach to Arcyriaflavin‐A and Unsymmetrical Analogues.

Adeva, Marta; Buono, Frédéric G.; Caballero, Esther; Medarde, Manuel; Tomé, Fernando

doi:10.1002/chin.200041179

Cited by 6 publications

(10 citation statements)

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“…The construction of the indolo[2,3-a]pyrrolo[3,4-c]carbazole framework was achieved by successive Diels-Alder cycloaddi- . 842 This method was also applied to the synthesis of 3-methoxy-6phenylarcyriaflavin A. 842…”

Section: Total Synthesis Of Arcyriaflavin a By Fischer Indolizationmentioning

confidence: 99%

Isolation and Synthesis of Biologically Active Carbazole Alkaloids

2002

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Section: Total Synthesis Of Arcyriaflavin a By Fischer Indolizationmentioning

confidence: 99%

Isolation and Synthesis of Biologically Active Carbazole Alkaloids

2002

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“…32 Generation of the second indoyl moiety via nitrene insertion, use of 2,2′-bisindole as diene for a (4 + 2) Diels Alder cycloaddition with dimethyl acetylene dicarboxylate or N-phenylmaleimide have also been described. [33][34][35][36][37] An alternative and more common synthesis consisted of the selective 3-alkylation of indole with a dibromomaleimide using Grignard reagents to produce bisindoylmaleimides. This procedure often requires an oxidative photochemical benzannulation, carried out by irradiation in a low concen-trated solution, which limits the amount of formed product.…”

Section: Chemistrymentioning

confidence: 99%

“…Direct formation of the maleimide framework through reaction of indole-3-acetamidate or by an oxidative coupling of indolyl acetate dianion have been reported . Generation of the second indoyl moiety via nitrene insertion, use of 2,2‘-bisindole as diene for a (4 + 2) Diels Alder cycloaddition with dimethyl acetylene dicarboxylate or N- phenylmaleimide have also been described. − An alternative and more common synthesis consisted of the selective 3-alkylation of indole with a dibromomaleimide using Grignard reagents to produce bisindoylmaleimides. This procedure often requires an oxidative photochemical benzannulation, carried out by irradiation in a low concentrated solution, which limits the amount of formed product. − Palladium-catalyzed reactions or Wacker type reactions represent interesting alternatives to the photochemical step.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and Biological Evaluation of Novel Naphthocarbazoles as Potential Anticancer Agents

et al. 2005

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We report the efficient synthesis involving palladium-catalyzed reactions and biological evaluation of new naphthocarbazoles designed as potential anticancer agents. The use of 5- and 6-benzyloxyindoles generated three substitution sites which were successively exploited to introduce several hydrophilic side chains. The cytotoxicity of the newly designed compounds was evaluated on three cell lines. Several compounds showed a marked cytotoxicity with IC(50) values in the sub-micromolar range. This is the case for the 3-hydroxy-naphthopyrrolocarbazoledione 37, bearing a dimethylaminoethyl side chain, which is extremely cytotoxic to L1210 and DU145 cells (IC(50): 36 nM, 108 nM) and induces an accumulation of L1210 cells in the G2+M phases of the cell cycle. Some of the most cytotoxic compounds were tested for inhibition of CDK-5, GSK-3 and topoisomerase I, and their interaction with DNA was also evaluated. Interaction with DNA was detected, suggesting that nucleic acids represent a privileged target for these molecules.

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“…128 In 2000, Tomé and co-workers reported a hybrid approach to arcyriaavin A (45), wherein classical Fischer synthesis and Cadogan nitrene insertion were applied to indole ring constructions (Scheme 27). 129 From commercial 2-nitrobenzaldehyde (162), Wittig olenation gave ketone 163, which was converted to the diene 164 upon treatment with TBSOTf/ NEt 3 . Diels-Alder cycloaddition reaction with maleimides 165a or 165b gave the endo-cycloadducts 166a/b, which were deprotected to give ketones 167a/b.…”

Section: Scheme 18mentioning

confidence: 99%