110216-87-0Relevant articles and documents
Synthesis of aryl-heteroaryl ureas (AHUs) based on 4-aminoquinoline and their evaluation against the insulin-like growth factor receptor (IGF-1R)
Engen, William,O'Brien, Terrence E.,Kelly, Brendan,Do, Jacinda,Rillera, Liezel,Stapleton, Lance K.,Youngren, Jack F.,Anderson, Marc O.
experimental part, p. 5995 - 6005 (2010/09/30)
The insulin-like growth factor receptor (IGF-1R) is a receptor tyrosine kinase (RTK) involved in all stages of the development and propagation of breast and other cancers. The inhibition of IGF-1R by small molecules remains a promising strategy to treat cancer. Herein, we explore SAR around previously characterized lead compound (1), which is an aryl-heteroaryl urea (AHU) consisting of 4-aminoquinaldine and a substituted aromatic ring system. A library of novel AHU compounds was prepared based on derivatives of the 4-aminoquinoline heterocycle (including various 2-substituted derivatives, and naphthyridines). The compounds were screened for in vitro inhibitory activity against IGF-1R, and several compounds with improved activity (3-5 μM) were identified. Furthermore, a computational docking study was performed, which identifies a fairly consistent lowest energy mode of binding for the more-active set of inhibitors in this series, while the less-active inhibitors do not adopt a consistent mode of binding.
MODULATION OF CHEMOSENSORY RECEPTORS AND LIGANDS ASSOCIATED THEREWITH
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Page/Page column 71, (2009/01/20)
The present invention provides screening methods for identifying modifiers of chemosensory receptors and their ligands, e.g., by determining whether a test entity is suitable to interact with one or more interacting sites within the Venus flytrap domains of the chemosensory receptors as well as modifiers capable of modulating chemosensory receptors and their ligands.
4-Hydroxy-2-quinolones. 93. Synthesis and biological properties of 2-hydroxy-4-imino-1,4-dihydroquinoline-3-carboxylic acid N-R-amides
Ukrainets,Sidorenko,Gorokhova,Jaradat
, p. 475 - 487 (2008/02/02)
Various methods of synthesizing amides of 2-hydroxy-4-imino-1,4- dihydroquinoline-3-carboxylic acids have been studied. Results of investigations on the antitubercular and antiinflammatory activity of the obtained compounds are discussed. 2006 Springer Sc
A new application of diphenylphosphorylazide (DPPA) reagent: Convenient transformations of quinolin-4-one, pyridin-4-one and quinazolin-4-one derivatives into the 4-azido and 4-amino counterparts
Aizikovich, Alexander,Kuznetsov, Vladimir,Gorohovsky, Sofia,Levy, Amalia,Meir, Simha,Byk, Gerardo,Gellerman, Garry
, p. 4241 - 4243 (2007/10/03)
Herein, we describe a transformation of the oxo-function of a series of quinolin/pyridin/quinazolin-4-ones into 4-azido and thence into 4-amino derivatives in moderate yields by a very short and convenient new procedure using DPPA (diphenylphosphoryl azide) as reagent. A mechanism for this interesting new application of DPPA is suggested based on the identification of some of the intermediates.
Regioselective Azidation of 2,4-Dichloroquinolines
Steinschifter, Waltraud,Stadlbauer, Wolfgang
, p. 311 - 318 (2007/10/02)
Reactions of 2,4-dichloroquinolines (2a-f) with sodium azide in DMF lead either regioselectively to 4-azido-2-chloroquinolines (3a-f) or with excess of sodium azide and catalysts to 5-azido-tetrazoloquinolines (4a-f). 2,4-Dichloroquinolines (2g-i) having electron donating substituents in 3-position react with sodium azide in DMF to a mixture of 4-azido-2-chloroquinolines (3g-i) and 5-chlorotetrazoloquinolines (5g-i).When the reaction of the 2,4-dichloroquinolines (2a-i) with sodium azide is carried out in ethanol with addition of methanesulfonic acid, regioselectively 5-chloro-tetrazoloquinolines (5a-i) are obtained.Structural assignments of 3 and 5 have been carried out by 13C-NMR spectra, IR spectra and degradation reactions of the azido- and tetrazolo group to aminoquinolines (7 and 10) via iminophosphoranes (8 and 9).It could be shown that in 2-azido/tetrazolo-quinolines (4 and 5) the tetrazole ring structure is the dominant species.
Methods for the Synthesis of 4-Azido-2(1H)-quinolones
Stadlbauer, Wolfgang
, p. 1305 - 1324 (2007/10/02)
4-Hydroxy-2-quinolones 1 are generally found to be converted to the 4-azidocompounds 3 via the 4-chloroquinolones 2, the 4-tosyloxyquinolones 6, or the 4-aminoquinolones 4, respectively.Choice of the reaction conditions and yields depend on the substituen