39883-47-1Relevant academic research and scientific papers
Design, synthesis and biological evaluation of arylpyridin-2-yl guanidine derivatives and cyclic mimetics as novel msk1 inhibitors. An application in an asthma model
Bihel, Frédéric,Bollenbach, Maud,Bourguignon, Jean-Jacques,Camelin, Guillaume,Daubeuf, Fran?ois,Frossard, Nelly,Nemska, Simona,Obrecht, Adeline,Rognan, Didier,Schmitt, Martine,Villa, Pascal,Wagner, Patrick
, (2021/06/21)
Mitogen-and Stress-Activated Kinase 1 (MSK1) is a nuclear kinase, taking part in the activation pathway of the pro-inflammatory transcription factor NF-kB and is demonstrating a therapeutic target potential in inflammatory diseases such as asthma, psoriasis and atherosclerosis. To date, few MSK1 inhibitors were reported. In order to identify new MSK1 inhibitors, a screening of a library of low molecular weight compounds was performed, and the results highlighted the 6-phenylpyridin-2-yl guanidine (compound 1a, IC50~18 μM) as a starting hit for structure-activity relationship study. Derivatives, homologues and rigid mimetics of 1a were designed, and all synthesized compounds were evaluated for their inhibitory activity towards MSK1. Among them, the non-cytotoxic 2-aminobenzimidazole 49d was the most potent at inhibiting significantly: (i) MSK1 activity, (ii) the release of IL-6 in inflammatory conditions in vitro (IC50~2 μM) and (iii) the inflammatory cell recruitment to the airways in a mouse model of asthma.
DERIVATIVES OF 2-AMINOPYRIDINE AS ADENOSINE A2B RECEPTOR ANTAGONISTS AND LIGANDS OF THE MELATONIN MT3 RECEPTORS
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Page/Page column 26-27, (2016/09/22)
The present invention relates to novel pyridine derivatives of formula (I) as A2B adenosine receptor antagonists and ligands of MT3 melatonin receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by antagonizing the adenosine A2B receptor and by inhibition of MT3 melatonin receptor, such as respiratory disease, metabolic disorders, neurological disorders and cancer.
Tetraphosphine/palladium-catalyzed Suzuki-Miyaura coupling of heteroaryl halides with 3-pyridine- and 3-thiopheneboronic acid: An efficient catalyst for the formation of biheteroaryls
Wang, Kun,Fu, Qi,Zhou, Rong,Zheng, Xueli,Fu, Haiyan,Chen, Hua,Li, Ruixiang
, p. 232 - 238 (2013/05/08)
An easily prepared tetraphosphine N,N,N′,N′- tetra(diphenylphosphinomethyl)-1,2-ethylenediamine (L1) associated with [Pd(η3-C3H5)Cl]2 affords an efficient catalyst for Suzuki-Miyaura coupling of 3-pyridineboronic acid with heteroaryl bromides. Reaction could be performed with as little as 0.02 mol% catalyst and a high turnover number of 2500 is obtained. A wide range of substrates is investigated with satisfactory yields, and good compatibility with aminogroup-substituted pyridines and unprotected indole is exhibited. This protocol can also be applied successfully to the reaction of heteroaryl bromides with 3-thiopheneboronic acid. This Pd-tetraphosphine catalyst efficiently restrains the poisoning effect from heteroaryls, and shows good stability and longevity. Copyright 2013 John Wiley & Sons, Ltd. An easily prepared tetraphosphine L1 was successfully used in Pd catalyzed Suzuki reaction of heteroaryl bromides with 3-pyridineboronic acid. A high turnover number of 2 500 was achieved and a wide range of heteroaryl halides including aminopyridines and indole was tolerated. With this protocol the coupling of 3-thiopheneboronic acid with heteroaryl bromides could also proceed in good yields. This catalyst system efficiently restrained poisoning effect from heteroaryls, and exhibited good stability and longevity. Copyright
2-Pyridyl and 3-pyridylzinc bromides: direct preparation and coupling reaction
Kim, Seung-Hoi,Rieke, Reuben D.
scheme or table, p. 3135 - 3146 (2010/06/13)
A facile synthetic approach to the direct preparation of 2-pyridyl and 3-pyridylzinc bromides has been demonstrated using Rieke zinc with 2-bromopyridine and 3-bromopyridine, respectively. A variety of different electrophiles have been coupled with the resulting organozinc reagents to give the corresponding cross-coupling products in moderate to good yields.
Transition-metal-catalyzed carbon-nitrogen and carbon-carbon bond-forming reactions
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Page/Page column 27; Sheet 4, (2008/06/13)
One aspect of the present invention relates to ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in various transition-metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition-metal-catalyzed reactions, including the range of suitable substrates, number of catalyst turnovers, reaction conditions, and efficiency. For example, improvements have been realized in transition metal-catalyzed: aryl amination reactions; aryl amidation reactions; Suzuki couplings; and Sonogashira couplings. In certain embodiments, the invention relates to catalysts and methods of using them that operate in aqueous solvent systems.
INHIBITORS OF HISTONE DEACETYLASE
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Page/Page column 55-56, (2010/02/14)
The invention relates to a series of compounds useful for inhibiting histone deacetylase (HDAC) enzymatic activity. The invention also provides a method for inhibiting histone descetylase in a cell using said compounds as well as a method for treating cell proliferative diseases and conditions using said HDAC inhibitors. Further, the invention provides pharmaceutical compositions comprising the HDAC inhibiting compounds and a pharmaceutically acceptable carrier.
General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water
Anderson, Kevin W.,Buchwald, Stephen L.
, p. 6173 - 6177 (2007/10/03)
Amphiphilic phosphine ligands (see structures; Cy = cyclohexyl) were prepared and utilized in palladium-catalyzed Suzuki-Miyaura and Sonogashira coupling reactions in water or water/organic biphasic solvents, providing excellent yields of functionalized b
