166338-06-3Relevant articles and documents
Copper-Catalyzed Aminoarylation of Alkenes via Aminyl Radical Addition and Aryl Migration
Wang, Jin-Lin,Liu, Mei-Ling,Zou, Jian-Yu,Sun, Wen-Hui,Liu, Xue-Yuan
supporting information, p. 309 - 313 (2022/01/04)
We describe a new strategy for aminoarylation of alkenes by copper-catalyzed smiles rearrangement using O-benzoylhydroxylamines as the amine reagent. This method affords various β-amino amide derivatives possessing a quaternary carbon center with wide functional group tolerance and high regioselectivity. The mechanistic studies indicate that the transformation can involve aminyl radical intermediates under acid-free condition.
Rational Design, Optimization, and Biological Evaluation of Novel MEK4 Inhibitors against Pancreatic Adenocarcinoma
Kwong, Ada J.,Munshi, Hidayatullah G.,Oelschlager, Hannah E.,Pham, Thao N. D.,Scheidt, Karl A.
supporting information, p. 1559 - 1567 (2021/10/04)
Growth, division, and development of healthy cells relies on efficient response to environmental survival cues. The conserved mitogen-activated protein kinase (MAPK) family of pathways interface extracellular stimuli to intracellular processes for this purpose. Within these pathways, the MEK family has been identified as a target of interest due to its clinical relevance. Particularly, MEK4 has drawn recent attention for its indications in pancreatic and prostate cancers. Here, we report two potent MEK4 inhibitors demonstrating significant reduction of phospho-JNK and antiproliferative properties against pancreatic cancer cell lines. Furthermore, molecular inhibition of MEK4 pathway activates the MEK1/2 pathway, with the combination of MEK1/2 and MEK4 inhibitors demonstrating synergistic effects against pancreatic cancer cells. Our inhibitors provided insight into the crosstalk between MAPK pathways and new tools for elucidating the roles of MEK4 in disease states, findings which will pave the way for better understanding of the MAPK pathways and development of additional probes.
COMPOUNDS AND METHODS FOR TREATING CANCER
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Paragraph 0190; 0233-0235, (2020/12/19)
Substituted cinnamamide compounds and analogs, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or ameliorate cancer are provided.
3-cyclopropyl-N-phenylbenzenesulfonamide and preparation method thereof
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Paragraph 0005; 0010-0013; 0018-0021, (2020/04/29)
The invention discloses 3-cyclopropyl-N-phenylbenzenesulfonamide and a preparation method thereof. The preparation method comprises the following steps: dissolving 3-bromobenzenesulfonic acid and aniline in pyridine, then adding a condensing agent EDC-HCl, and carrying out a reaction for 2 to 3 h at a temperature of 50 to 80 DEG C so as to obtain 3-bromo-N-phenylbenzenesulfonamide; dissolving 3-bromo-N-phenylbenzenesulfonamide into a dioxane solution; adding cyclopropylboronic acid, sodium carbonate, an aqueous solution and Pd (dppf) Cl2, reacting a mixed system at 110 DEG C for 8-10 hours ina nitrogen atmosphere, and carrying out aftertreatment to obtain 3-cyclopropyl-N-phenylbenzenesulfonamide. The preparation method has the advantages of relatively mild conditions, easy product treatment and purification and suitability for batch preparation. The preparation method provided by the invention is easy to operate in reaction, high in product yield and suitable for batch preparation, sothat the preparation method of 3-cyclopropyl-N-phenylbenzenesulfonamide has an important application value.
Synthesis of: N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium
Jiang, Jun,Zeng, Sheng,Chen, De,Cheng, Chaozhihui,Deng, Wei,Xiang, Jiannan
supporting information, p. 5016 - 5020 (2018/07/25)
A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust serves as the sole reductant in the transformation and it can be easily performed on a large scale.
COMPOUNDS AND METHODS
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Page/Page column 29, (2013/05/22)
Disclosed are compounds having the formula (I), wherein Ar, X, and R are as defined herein, and methods of making and using the same.
Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids
Debergh, J. Robb,Niljianskul, Nootaree,Buchwald, Stephen L.
supporting information, p. 10638 - 10641 (2013/08/23)
A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions.
Discovery of a novel series of potent and orally bioavailable phosphoinositide 3-kinase γ inhibitors
Leahy, James W.,Buhr, Chris A.,Johnson, Henry W. B.,Kim, Byung Gyu,Baik, Taegon,Cannoy, Jonah,Forsyth, Timothy P.,Jeong, Joon Won,Lee, Matthew S.,Ma, Sunghoon,Noson, Kevin,Wang, Longcheng,Williams, Matthew,Nuss, John M.,Brooks, Eric,Foster, Paul,Goon, Leanne,Heald, Nathan,Holst, Charles,Jaeger, Christopher,Lam, Scott,Lougheed, Julie,Nguyen, Lam,Plonowski, Arthur,Song, Joanne,Stout, Thomas,Wu, Xiang,Yakes, Michael F.,Yu, Peiwen,Zhang, Wentao,Lamb, Peter,Raeber, Olivia
experimental part, p. 5467 - 5482 (2012/09/25)
The phosphoinositide 3-kinases (PI3Ks) have been linked to an extraordinarily diversified group of cellular functions making these enzymes compelling targets for the treatment of disease. A large body of evidence has linked PI3Kγ to the modulation of autoimmune and inflammatory processes making it an intriguing target for drug discovery. Our high-throughput screening (HTS) campaign revealed two hits that were nominated for further optimization studies. The in vitro activity of the first HTS hit, designated as the sulfonylpiperazine scaffold, was optimized utilizing structure-based design. However, nonoptimal pharmacokinetic properties precluded this series from further studies. An overlay of the X-ray structures of the sulfonylpiperazine scaffold and the second HTS hit within their complexes with PI3Kγ revealed a high degree of overlap. This feature was utilized to design a series of hybrid analogues including advanced leads such as 31 with desirable potency, selectivity, and oral bioavailability.
METHODS OF SYNTHESIS OF CERTAIN HYDROXAMIC ACID COMPOUNDS
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Page/Page column 51-52, (2009/05/29)
The present invention pertains to the general field of chemical synthesis, and more particularly to methods for the synthesis of certain hydroxamic acid compounds, and in particular, (E)-N-hydroxy-3-(3-phenylsulfamoyl-phenyl)-acrylamide, also known as PXD
CARBOXYLIC DERIVATIVES FOR USE IN THE TREATMENT OF CANCER
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Page/Page column 61, (2009/07/25)
The invention provides novel compounds of formula (I), wherein: R1 is a radical derived from one of the known ring systems; R2 is a phenyl radical optionally substituted; Xn represents a birradical selected from the group consisting of: -(CH2)1-4-, (C2-C4)-alkenyl, (C2-C4)alkynyl, -S-(CH2)1-3-#, and -(CH2)1-3-O-#; wherein the symbol # indicates the position at which Xn is attached to R1; Yn is a birradical selected from the group consisting of: -(CH2)2-4-, -S-(CH2)1-3#, and -O-(CH2)1-3-#,; where in the symbol # indicates the position at which Yn is attached to R2; and R3 is a radical selected from the group consisting of: -OR4. The compounds of formula (I) are useful in the treatment of cancer
