- Concise Total Syntheses of Paullone and Kenpaullone via Cyanide-Catalyzed Intramolecular Imino-Stetter Reaction
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Highly concise total syntheses of paullone and kenpaullone were developed. Cyanide-catalyzed intramolecular imino-Stetter reaction of aldimines derived from methyl 2-aminocinnamate derivatives and 2-nitrobenzaldehyde provided 2-(2′-nitrophenyl)indole-3-acetic acid derivatives. Subsequent reduction of the nitro group with zinc under acidic conditions to an amino group followed by spontaneous lactam formation allowed for the total syntheses of paullone and kenpaullone to be completed in two steps starting from commercially available materials. The direct use of a nitro group as the precursor of an amino group present in the phenyl ring at the 2-position in the indole ring significantly streamlined the total syntheses of these target molecules..
- Lee, Sang Eun,Lee, Seong Jong,Cheon, Cheol-Hong
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p. 4247 - 4253
(2017/09/12)
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- New synthetic approach to paullones and characterization of their SIRT1 inhibitory activity
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A series of 7,12-dihydroindolo[3,2-d][1]benzazepine-6(5H)-ones (paullones) substituted at C9/C10 (Br) and C2 (Me, CF3, CO2Me) have been synthesized by a one-pot Suzuki-Miyaura cross-coupling of an o-aminoarylboronic acid and methyl 2-iodoindoleacetate followed by intramolecular amide formation. Other approaches to the paullone scaffold based on Pd-catalyzed C-H activation were unsuccessful. In vitro enzymatic assay with recombinant human SIRT-1 indicated a strong inhibitory profile for the series, in particular the analogue with a methoxycarbonyl group at C2 and a bromine at C9. These compounds are, in general, inducers of granulocyte differentiation of the U937 acute leukemia cell line and cause a marked increase in pre-G1 of the cell cycle.
- Soto, Sara,Vaz, Esther,Dell'Aversana, Carmela,Alvarez, Rosana,Altucci, Lucia,De Lera, Angel R.
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p. 2101 - 2112
(2012/04/23)
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- Synthesis of paullone and kenpaullone derivatives by photocyclization of 2-(2-chloro-1H-indol-3-yl)-N-arylacetamides
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An efficient synthesis of paullone and kenpaullone derivatives in moderate to high yields has been achieved through photocyclizations of (2-chloro-1H-indole-3-yl)-N-arylacetamides in acetone at room temperature. Paullone and kenpaullone have been obtained
- Li, Zhanshan,Lu, Nianhong,Wang, Lihong,Zhang, Wei
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p. 1019 - 1024
(2012/03/27)
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- Development of 5-benzylpaullones and paullone-9-carboxylic acid alkyl esters as selective inhibitors of mitochondrial malate dehydrogenase (mMDH)
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A collection of paullones was tested for inhibitory activity against mitochondrial malate dehydrogenase (mMDH) as a biological target for antiproliferative activity. Based on the results of this screening, 5-benzylpaullones and paullone-9-carboxylic acid alkyl esters were developed as selective mMDH inhibitors. The new derivatives did not show noteworthy antiproliferative activity when tested on a panel of cancer cell lines, suggesting that mMDH inhibition is of minor relevance for the growth inhibition caused by paullones.
- Becker, Anja,Kohfeld, Simone,Lader, Annette,Preu, Lutz,Pies, Tanja,Wieking, Karen,Ferandin, Yoan,Knockaert, Marie,Meijer, Laurent,Kunick, Conrad
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experimental part
p. 335 - 342
(2010/03/25)
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- Tumor-inhibiting anellated azepinone derivatives
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This invention relates to anellated azepinone derivatives, a method of their production, metal complexes of the anellated azepinone derivatives as well as their use in the treatment of tumor diseases.
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Page/Page column 6
(2010/02/15)
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- PLANT GROWTH REGULATION
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The present invention relates to a new class of plant growth regulators. In particular, the invention relates to fused azepinone derivative of general formula (I) or an agriculturally acceptable salt thereof wherein X is CO2R2 or H;
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Page/Page column 21
(2008/06/13)
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- TUMOUR-INHIBITING ANNELLATED AZEPINONE DERIVATIVES
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The invention relates to annellated azepinone derivatives, to a method for the production thereof, to metal complexes of the annellated azepinone derivatives, and to the use of the same for treating tumour diseases.
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Page/Page column 18
(2010/02/07)
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- Synthesis of 7,12-Dihydro-indolo[3,2-d][1]benzazepin-6-(5H)-ones and 6,11-Dihydro-thieno-[3',2':2,3]azepino[4,5-b]indol-5(4H)-one
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The title compounds 4 and 6 were prepared by Fischer indole synthesis. 4a is substituted in 10-position by reaction with bromine in glacial acetic acid. A fast ring inversion is observed for the azepine ring in 4 and 6.
- Kunick
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p. 297 - 299
(2007/10/02)
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