188637-63-0Relevant articles and documents
General C-H Arylation Strategy for the Synthesis of Tunable Visible Light-Emitting Benzo[a]imidazo[2,1,5-c,d]indolizine Fluorophores
Lévesque, éric,Bechara, William S.,Constantineau-Forget, Léa,Pelletier, Guillaume,Rachel, Natalie M.,Pelletier, Joelle N.,Charette, André B.
, p. 5046 - 5067 (2017/05/24)
Herein we report the discovery of the benzo[a]imidazo[2,1,5-c,d]indolizine motif displaying tunable emission covering most of the visible spectrum. The polycyclic core is obtained from readily available amides via a chemoselective process involving Tf2O-mediated amide cyclodehydration, followed by intramolecular C-H arylation. Additionally, these fluorescent heterocycles are easily functionalized using electrophilic reagents, enabling divergent access to varied substitution. The effects of said substitution on the compounds' photophysical properties were rationalized by density functional theory calculations. For some compounds, emission wavelengths are directly correlated to the substituent's Hammett constants. Easily introduced nonconjugated reactive functional groups allow the labeling of biomolecules without modification of emissive properties. This work provides a straightforward platform for the synthesis of new moderately bright fluorescent dyes remarkable for their chemical stability, predictability, and unusually high excitation-emission differential.
Novel tricyclic inhibitors of IKK2: Discovery and SAR leading to the identification of 2-methoxy-N-((6-(1-methyl-4-(methylamino)-1,6- dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-7-yl)pyridin-2-yl)methyl)acetamide (BMS-066)
Watterson, Scott H.,Langevine, Charles M.,Van Kirk, Katy,Kempson, James,Guo, Junquing,Spergel, Steven H.,Das, Jagabandhu,Moquin, Robert V.,Dyckman, Alaric J.,Nirschl, David,Gregor, Kurt,Pattoli, Mark A.,Yang, Xiaoxia,McIntyre, Kim W.,Yang, Guchen,Galella, Michael A.,Booth-Lute, Hollie,Chen, Laishun,Yang, Zheng,Wang-Iverson, David,McKinnon, Murray,Dodd, John H.,Barrish, Joel C.,Burke, James R.,Pitts, William J.
, p. 7006 - 7012 (2012/01/13)
The synthesis, structure-activity relationships (SAR), and biological results of pyridyl-substituted azaindole based tricyclic inhibitors of IKK2 are described. Compound 4m demonstrated potent in vitro potency, acceptable pharmacokinetic and physicochemical properties, and efficacy when dosed orally in a mouse model of inflammatory bowel disease.
A convenient one-pot preparation and applications of high loading benzhydrylamine solid phase linkers
Torr, Jane E.,Large, Jonathan M.,McDonald, Edward
, p. 1951 - 1954 (2007/10/03)
A rapid and convenient one-pot route to solid supported benzhydrylamine linkers with high chemical loading is described. Such linkers possess differing levels of acid lability, which could be exploited in solid phase synthesis applications. They have also been utilised to prepare novel and potentially useful N-methylated derivatives. We also report an effective on-resin purification strategy for reductive amination, which is facilitated by the varying acid lability of resin-linked secondary amines or tertiary amine by-products.