543745-42-2Relevant academic research and scientific papers
Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction
Wilkie, Ross. P.,Neal, Andrew R.,Johnston, Craig A.,Voute, Nicholas,Lancefield, Christopher S.,Stell, Matthew D.,Medda, Federico,Makiyi, Edward F.,Turner, Emma M.,Stephen Ojo,Slawin, Alexandra M. Z.,Lebl, Tomas,Mullen, Peter,Harrison, David J.,Ireland, Chris M.,Westwood, Nicholas J.
supporting information, p. 10747 - 10750 (2016/09/07)
The synthesis of dehaloperophoramidine, a non-halogenated derivative of the marine natural product perophoramidine, and its biological activity towards HCT116, HT29 and LoVo colorectal carcinoma cells is reported. A [3,3]-Claisen rearrangement and an epoxide opening/allylsilylation reaction installed the contiguous all-carbon quaternary stereocentres with the required relative stereochemistry.
Synthesis and antiplasmodial activity of aminoalkylamino-substituted neocryptolepine derivatives
El Sayed, Ibrahim,Van Der Veken, Pieter,Steert, Koen,Dhooghe, Liene,Hostyn, Steven,Van Baelen, Gitte,Lemière, Guy,Maes, Bert U. W.,Cos, Paul,Maes, Louis,Joossens, Jurgen,Haemers, Achiel,Pieters, Luc,Augustyns, Koen
supporting information; experimental part, p. 2979 - 2988 (2010/01/16)
A series of chloro- and aminoalkylamino-substituted neocryptolepine (5-methyl-5H-indolo[2,3-b]quinoline) derivatives were synthesized and evaluated as antiplasmodial agents. The evaluation also included cytotoxicity (MRC5 cells), inhibition of β-hematin f
Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
Bergman, Jan,Engqvist, Robert,St?lhandske, Claes,Wallberg, Hans
, p. 1033 - 1048 (2007/10/03)
Reflux of equimolecular amounts 2-aminobenzylamine and isatins in acetic acid produced indolo[3,2-c]quinolin-6-ones in good yields. A proposed mechanism involving initial formation of a spiro compound is given. This isolable intermediate subsequently rearranges via a sequential isocyanate ring opening and a cyclisation process to a urea derivative which finally cyclized to the indolo[3,2-c]quinolin-6-ones. The urea derivative could be prepared separately and cyclized selectively to indolo[3,2-c]quinolin-6-one. Reaction of N-acetylisatin with 2-aminobenzylamine at room temperature yielded the 1,4-benzodiazepinone 3-(2-acetamidophenyl)-1,5-dihydro-1,4-benzodiazepin-2-one whereas its isomer 2(2-acetamidophenyl)-4,5-dihydro-1,4-benzodiazepin-3-one was obtained from 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide in acetic acid at room temperature. The previously unknown linear isomer of indolo[3,2-c]quinolin-6-one, i.e. indolo[2,3-b]quinolin-11-one, has been prepared by thermal (260°C) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxylate.
