4462-17-3Relevant academic research and scientific papers
Substituted pteridinones as p90 ribosomal S6 protein kinase (RSK) inhibitors: A structure-activity study
Backos, Donald S.,Casalvieri, Kimberly A.,Matheson, Christopher J.,Reigan, Philip
, (2020/01/28)
The activity of p90 ribosomal S6 kinase 2 (RSK2) has emerged as an attractive target for cancer therapy due to its role in the regulation of diverse cellular processes, such as cell transformation and proliferation. Several pan-RSK inhibitors have been identified with BI-D1870 and the pseudo-analogs LJH685 and LJI308 being the most selective, potent, and frequently used small molecule inhibitors. We designed and synthesized a series of pteridinones and pyrimidines to evaluate the structural features of BI-D1870 that are required for RSK2 inhibition. We have identified inhibitors of RSK2 activity, evaluated their target engagement in cells, and measured their effect on cell viability and cytotoxicity in the MOLM-13 acute myeloid leukemia (AML) cell line. The results of our studies support that RSK2 inhibition can be achieved in MOLM-13 cells without potent cytotoxicity. The structure-activity data from this study will be used as a platform to develop novel RSK2 inhibitors.
Divergent Coupling of Alcohols and Amines Catalyzed by Isoelectronic Hydride MnIand FeIIPNP Pincer Complexes
Mastalir, Matthias,Glatz, Mathias,Gorgas, Nikolaus,St?ger, Berthold,Pittenauer, Ernst,Allmaier, Günter,Veiros, Luis F.,Kirchner, Karl
supporting information, p. 12316 - 12320 (2016/08/24)
Herein, we describe an efficient coupling of alcohols and amines catalyzed by well-defined isoelectronic hydride MnIand FeIIcomplexes, which are stabilized by a PNP ligand based on the 2,6-diaminopyridine scaffold. This reaction is an environmentally benign process implementing inexpensive, earth-abundant non-precious metal catalysts, and is based on the acceptorless alcohol dehydrogenation concept. A range of alcohols and amines including both aromatic and aliphatic substrates were efficiently converted in good to excellent isolated yields. Although in the case of Mn selectively imines were obtained, with Fe—exclusively monoalkylated amines were formed. These reactions proceed under base-free conditions and required the addition of molecular sieves.
Ruthenium-catalyzed N-alkylation of amines with alcohols under mild conditions using the borrowing hydrogen methodology
Enyong, Arrey B.,Moasser, Bahram
, p. 7553 - 7563 (2014/09/17)
Using a simple amino amide ligand, ruthenium-catalyzed one-pot alkylation of primary and secondary amines with simple alcohols was carried out under a wide range of conditions. Using the alcohol as solvent, alkylation was achieved under mild conditions, even as low as room temperature. Reactions occurred with high conversion and selectivity in many cases. Reactions can also be carried out at high temperatures in organic solvent with high selectivity using stoichiometric amounts of the alcohol.
Structure-activity relationships of small molecule inhibitors of RAGE-Aβ binding
Ross, Nathan T.,Deane, Rashid,Perry, Sheldon,Miller, Benjamin L.
, p. 7653 - 7658 (2013/08/23)
The Receptor for Advanced Glycation Endproducts ('RAGE') mediates transport of amyloid-β peptide (Aβ) into the brain, and is therefore an important target for the development of therapeutic agents for Alzheimer's disease. We describe structure-activity relationships for inhibition of RAGE-Aβ binding, derived from the analysis of a library of tertiary amides.
α,β-Unsaturated imines via Ru-catalyzed coupling of allylic alcohols and amines
Rigoli, Jared W.,Moyer, Sara A.,Pearce, Simon D.,Schomaker, Jennifer M.
, p. 1746 - 1749 (2012/04/23)
A convenient synthesis of α,β-unsaturated imines requiring only an allylic alcohol, an amine and a Ru catalyst has been developed. The use of large excesses of oxidant and the purification of sensitive intermediates can be avoided.
Microwave-assisted solventless reaction of iridium-catalyzed alkylation of amines with alcohols in the absence of base
Zhang, Weixing,Dong, Xiaochun,Zhao, Weili
supporting information; experimental part, p. 5386 - 5389 (2011/11/29)
Microwave-assisted iridium catalyzed alkylation of amines with alcohols was undertaken under solvent-free and base-free conditions. Such alkylation reactions are green, atom-economic, and effective for mono-, di-, and triaklyation of amines. Good isolated yields were obtained for mono- and dialkylated amines using stoichiometric amounts of amines and alcohols, in the presence of 1 mol % [Cp*IrCl2]2. Reasonable yields of trialkylated products were obtained using 4 equiv of alcohols.
Osmium and ruthenium catalysts for dehydrogenation of alcohols
Bertoli, Marcello,Choualeb, Aldjia,Lough, Alan J.,Moore, Brandon,Spasyuk, Denis,Gusev, Dmitry G.
scheme or table, p. 3479 - 3482 (2011/09/20)
A series of pincer-type complexes of Os and Ru have been synthesized and investigated in catalytic alcohol dehydrogenation. The hydrides OsHCl(CO)[HN(C2H4PiPr2)2] and OsH2(CO)[HN(C2H4PiPr2)2] possess good air, moisture, and thermal stability and are outstanding versatile dehydrogenation catalysts for primary alcohols for reactions of transfer hydrogenation, dehydrogenative coupling, and amine alkylation.
Synthesis and properties of pentane amino derivatives
Talybov,Mamedbeili,Abbasov,Kochetkov
experimental part, p. 2455 - 2459 (2011/04/16)
Synthesis of pentane amino derivatives by the reaction of the corresponding amines with 1-bromopentanes of n-and iso-structure by environmentally safe methods in water medium was carried out. The structure of the compounds obtained was confirmed by elemental analysis, IR, 1H and 13C NMR spectroscopy. The products synthesized were tested as reagents for the suppression of growth of the sulfate-reducing bacteria and as the anticorrosive substances. It was found that they are effective bactericides for the sulfate-reducing bacteria and exhibit high anticorrosive properties. Pleiades Publishing, Ltd., 2010.
Hydroamination of carbonyl compounds with oximes
Tarasevich,Kozlov
, p. 379 - 383 (2007/10/03)
N-alkyl(cycloalkyl)benzylamines, p-fluorobenzylamines, (1-phenylethyl) amines, [1-(p-fluorophenyl)ethyl]amines were synthesized by hydroamination of aldehydes and ketones with oximes.
Indirect monoalkylation of primary and secondary amines by reductive decyanation of α-aminonitriles with sodium cyanoborohydride-mercury bis(trifluoroacetate)
Sassaman, Mark B.
, p. 10835 - 10840 (2007/10/03)
Secondary and tertiary amines are prepared from α-aminonitriles by selective reductive cleavage of the cyanide moiety. The α-aminonitriles in this case, function as 'masked' imine or iminium ions and are 'unmasked' by mercury(II) in the presence of sodium cyanoborohydride to obtain the reduced product. Secondary amines may be prepared indirectly from primary amines in good yield without danger of over alkylation.
