129708-07-2Relevant academic research and scientific papers
Indol-2-yl ethanones as novel indoleamine 2,3-dioxygenase (IDO) inhibitors
Dolusic, Eduard,Larrieu, Pierre,Blanc, Sebastien,Sapunaric, Frederic,Norberg, Bernadette,Moineaux, Laurence,Colette, Delphine,Stroobant, Vincent,Pilotte, Luc,Colau, Didier,Ferain, Thierry,Fraser, Graeme,Galeni, Moreno,Frre, Jean-Marie,Masereel, Bernard,Van Den Eynde, Benoit,Wouters, Johan,Frederick, Raphael
experimental part, p. 1550 - 1561 (2011/03/22)
Indoleamine 2,3-dioxygenase (IDO) is a heme dioxygenase which has been shown to be involved in the pathological immune escape of diseases such as cancer. The synthesis and structure-activity relationships (SAR) of a novel series of IDO inhibitors based on the indol-2-yl ethanone scaffold is described. In vitro and in vivo biological activities have been evaluated, leading to compounds with IC50 values in the micromolar range in both tests. Introduction of small substituents in the 5- and 6-positions of the indole ring, indole N-methylation and variations of the aromatic side chain are all well tolerated. An iron coordinating group on the linker is a prerequisite for biological activity, thus corroborating the virtual screening results.
The synthesis of azaisomers of the triester of PQQ: 3H-pyrrolo[3,2-f]-, 1H-pyrrolo[3,2-h]-, and 7H-pyrrolo[2,3-h]quinolinequinone derivatives
Martin,Winkler
, p. 111 - 120 (2007/10/02)
We describe here the synthesis of the title compounds 3-5, starting from highly substituted aminoindoles. The annelated pyridine rings were built up in each case with dimethyl 4-oxoglutaconate according to Corey's procedure. All three o-quinone derivatives 3-5 are stable compounds, comparable to PQQ-triester. The azaisomers vary in biological activity from practically inactive to strong inhibition of the α-amidating enzyme or the ornithin decarboxylase.
Synthesis of Isoquinoline Derivatives by a Tandem Aza-Wittig/Electrocyclization Strategy and Preparation of the Unknown 1,9-Diazaphenalene Ring by a Consecutive Electrocyclic Ring Closure/Claisen Rearrangement/Intramolecular Amination Process
Molina, Pedro,Alajarin, Mateo,Vidal, Angel
, p. 6140 - 6147 (2007/10/02)
Treatment of iminophosphorane 3, derived from ethyl α-azido-2-(allyloxy)cinnamate, with aromatic isocyanates in toluene at 150 deg C leads to the corresponding isoquinoline derivatives 5 by a tandem electrocyclic ring closure/Claisen rearrangement of the intermediate carbodiimide.Fremy's salt promoted oxidation of compounds 5 yields the 5,8-isoquinolinequinone allides 6, which by heating undergo cyclization to 2H-pyranoisoquinolines 7.Iminophosphorane 14, derived from ethyl α-azido-2-(allyloxy)-3-methoxycinnamate, reacts with aromatic isocyanates to give thecorresponding carbodiimides, which by thermal treatment at 150 deg C undergo a consecutive electrocyclic ring closure/Claisen rearrangement/intramolecular amination process to give 1,9-diazaphenalene derivatives 18 in moderate yields.
