109130-61-2Relevant academic research and scientific papers
Synthesis and biological evaluation of analogues of cryptolepine, an alkaloid isolated from the suriname rainforest
Yang, Shu-Wei,Abdel-Kader, Maged,Malone, Stan,Werkhoven, Marga C. M.,Wisse, Jan H.,Bursuker, Isia,Neddermann, Kim,Fairchild, Craig,Raventos-Suarez, Carmen,Menendez, Ana T.,Lane, Kate,Kingston, David G. I.
, p. 976 - 983 (1999)
Bioassay-guided fractionation of an extract of a mixture of Microphilis guyanensis and Genipa americana collected in the rainforest of Suriname yielded the known alkaloid cryptolepine (2) as the major active compound in a yeast bioassay for potential DNA-damaging agents; the same compound was later reisolated from M. guyanensis. The structure of cryptolepine was identified unambiguously by spectral data and by its total synthesis. Several cryptolepine derivatives (3-29, 32-41) were synthesized based on modifications of the C-2, N-5, N-10, and C-11 positions. Two cryptolepine dimers (30, 31) were also prepared. The structure modifications did not result in compounds with a higher potency than the parent compound cryptolepine in the yeast assay system, although some derivatives did show significant activity. Selected compounds (6, 7, 17, 22, 23, 26, and 27) were also tested for cytotoxicity in mammalian cell culture, and two compounds showed significant cytotoxic activity.
Convenient synthesis of 10H-indolo[3,2-b]quinolines and 6H-indolo[2,3-b]quinolines by sequential chemoselective Suzuki reaction followed by double C-N coupling
Salman, Ghazwan Ali,Janke, Sophie,Pham, Ngo Nghia,Ehlers, Peter,Langer, Peter
, p. 1024 - 1032 (2018)
A convenient and regioselective synthesis of two series of indolo[2,3-b]quinolines, namely 10H-indolo[3,2-b]quinolines and 6H-indolo[2,3-b]quinolines, has been developed. The synthesis, proceeds in moderate to high yields, involving chemoselective palladium catalyzed Suzuki reaction of 2,3-dihaloquinolines with 2-bromophenylboronic acid, followed by a double Buchwald-Hartwig C-N coupling.
First synthesis of benzopyridoiodolium salts and twofold Buchwald-Hartwig amination for the total synthesis of quindoline
Letessier, Julien,Detert, Heiner
, p. 290 - 296 (2012/04/17)
The first synthesis of cyclic benzopyridoiodolium salts is described. These hypervalent iodine intermediates are used in an efficient strategy for the construction of the -carboline core. This novel approach involves a twofold palladium-catalyzed Buchwald
An Alternative Synthesis of 10H-Indolo[3,2-b]quinoline and its Selective N- Alkylation
Fan, Pingchen,Ablordeppey, Seth Y.
, p. 1789 - 1794 (2007/10/03)
A new and a more efficient synthesis of 10H-Indolo[3,2-b]quinoline (quindo line) is reported. The synthesis involved N-arylation of 3-aminoquinoline with triphenylbismuth diacet ate followed by oxidative cyclization using palladium (II) acetate. A selecti
ALKYLATION OF QUINDOLINE-11-CARBOXYLIC ACID
Degutis, Yu. A.,Ezyarskaite, A. B.
, p. 1114 - 1117 (2007/10/02)
The reaction between quindoline-11-carboxylic acid and alcohols in acid media gives the quindoline-11-carboxylate esters, but quindoline-11-carboxylic acid or its hydrochloride react with haloalkanes in the presence of basic catalysts and water binders to give 10-alkylquindoline-11-carboxylate esters. 10-Alkylquindolines were obtained similarly.Alkylation of 1-alkylquindoline-11-carboxylate esters in neutral media affords the quaternary salts.
