2216-16-2Relevant academic research and scientific papers
A Phosphine-Mediated Dearomative Skeletal Rearrangement of Dianiline Squaraine Dyes
Bacher, Emily P.,Koh, Kevin J.,Lepore, Antonio J.,Oliver, Allen G.,Wiest, Olaf,Ashfeld, Brandon L.
supporting information, p. 2853 - 2857 (2021/05/05)
A phosphorus(III)-mediated dearomatization of ortho-substituted dianiline squaraine dyes results in an unusual skeletal rearrangement to provide exotic, highly conjugated benzofuranone and oxindole scaffolds bearing a C3 side chain comprised of a linear conflagration of an enol, a phosphorus ylide, and 2,4-disubstituted aniline. Employing experimental and computational analysis, a mechanistic evaluation revealed a striking dependence on the acidity of the aniline ortho substituent. Notably, the rearrangement adducts underwent rapid and complete reversion to the parent squaraine in the presence of a Br?nsted acid.
DIARYLUREAS AS CB1 ALLOSTERIC MODULATORS
-
Paragraph 71; 113; 123, (2018/12/02)
The present invention provides novel diarylurea derivatives (compounds of formula (I)) and their uses. The compounds of the present invention are demonstrated to be allosteric modulators of the CB1 receptor, and therefore useful for the treatment of diseases and conditions mediated by CB1.
Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)
Lu, Yanli,Mao, Fei,Li, Xiaokang,Zheng, Xinyu,Wang, Manjiong,Xu, Qing,Zhu, Jin,Li, Jian
supporting information, p. 5099 - 5119 (2017/06/28)
Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFRα) kinases play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFRα dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRα. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PDGFRα-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 μM concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T670I tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.
CuI/DMPAO-catalyzed N-arylation of acyclic secondary amines
Zhang, Yu,Yang, Xinye,Yao, Qizheng,Ma, Dawei
supporting information; experimental part, p. 3056 - 3059 (2012/07/28)
DMPAO has been found to be a powerful ligand to enable copper-catalyzed coupling of aryl halides with aliphatic acyclic secondary amines take place under relatively mild conditions, and coupling of aryl halides with primary amines and cyclic secondary amines proceeds at low catalyst loading.
Amination of aryl bromides catalysed by supported palladium
Djakovitch, Laurent,Wagner, Michael,Koehler, Klaus
, p. 225 - 234 (2007/10/03)
Palladium particles immobilised onto a metal oxide support or Pd(0), Pd(II) and [Pd(NH3)4]2+ in NaY zeolite have been prepared and characterised. They exhibit a good activity towards the amination of aryl bromides using secondary amines such as piperidine and diethyl amine with a good regio-selectivity for these reactions. Low Pd concentrations (1 mol%) are required to observe a reasonable regio-selectivity. The catalysts can easily be separated from the reaction mixture (filtration) and reused without loss of activity and selectivity. The electronic nature of the aryl halides plays an important role for both the reaction yields and the regio-control of the reaction. It depends on the relation of the direct amination via a benzyne intermediate versus the Pd-catalysed route.
Synthesis and NMR-spectral characterization of N,N-dialkyl-3-nitroanilines, N,N-dialkyl-1,3-benzenediamines and their acyl derivatives
Katritzky, Alan R.,Rachwal, Bogumila,Rachwal, Stanislaw
, p. 337 - 345 (2007/10/02)
A recently discovered method for the synthesis of N,N-dialkyl-1,3-benzenediamines with two different alkyl groups is shown to be general.This is demonstrated by the synthesis of N-butyl-N-phenethyl-1,3-benzenediamine by the condensation of 3-nitroaniline with phenylacetaldehyde and benzotriazole, reduction of the adduct with sodium borohydride, acylation of the resulting N-phenethyl-3-nitroaniline with butyryl chloride, catalytic reduction of the nitro group by formic acid in the presence of triethylamine and palladium and finally reduction of the butyramide carbonyl group to the butyl substituent by lithium aluminium hydride.Several other routes were less efficient or failed completely.Classical methods for the synthesis of N,N-diethyl-1,3-benzenediamine were reexamined and improved.The recommended procedure involves alkylation of 3-nitroaniline with diethyl sulfate, trapping of N-ethyl-3-nitroaniline (by-product) by benzoylation, distillation of N,N-diethyl-3-nitro-aniline under reduced pressure and reduction of the nitro group by formic acid catalyzed by palladium.
Synthesis and Spectral Characterization of Blue Dyes of the Benzene Series
Thiel, W.,Mayer, R.,Jauer, E.-A.,Modrow, H.,Dost, H.
, p. 497 - 514 (2007/10/02)
53 Donor-acceptor substituted azo dyes of the benzene series were prepared by diazonium-coupling reactions (1a-s) or halogen-cyanide exchange (->2a-x, 3a-j).Described are the preparation of the amines 4a-m and the coupling compounds 5a-t and the procedure of diazotizing and coupling.The colouristic and spectroscopic data show that compounds of the general formula 1 are excellent brilliant blue azo dyes usefull for dyeing polyester material.
