- 3-Alkenyl-2-oxindoles: Synthesis, antiproliferative and antiviral properties against SARS-CoV-2
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Sets of 3-alkenyl-2-oxindoles (6,10,13) were synthesized in a facile synthetic pathway through acid dehydration (EtOH/HCl) of the corresponding 3-hydroxy-2-oxoindolines (5,9,12). Single crystal (10a,c) and powder (12a,26f) X-ray studies supported the stru
- Girgis, Adel S.,Panda, Siva S.,Srour, Aladdin M.,Abdelnaser, Anwar,Nasr, Soad,Moatasim, Yassmin,Kutkat, Omnia,El Taweel, Ahmed,Kandeil, Ahmed,Mostafa, Ahmed,Ali, Mohamed A.,Fawzy, Nehmedo G.,Bekheit, Mohamed S.,Shalaby, ElSayed M.,Gigli, Lara,Fayad, Walid,Soliman, Ahmed A.F.
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- Synthesis, biological evaluation and molecular docking of new sulfonamide-based indolinone derivatives as multitargeted kinase inhibitors against leukemia
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Series of novel sulfonamide-based 3-indolinones 3a-m and 4a-f were designed, synthesized and then their cytotoxic activity was evaluated against a panel of sixty cancer cell lines. This screening indicated that 4-(2-(5-fluoro-2-oxoindolin-3-ylidene)acetyl)phenyl benzenesulfonate (4f) possessed promising cytotoxicity against CCRF-CEM and SR leukemia cell lines with IC50 values 6.84 and 2.97 μM, respectively. Further investigation of the leukemic cytotoxicity of compound 4f was carried out by performing PDGFRα, VEGFR2, Aurora A/B and FLT3 enzyme assays and CCRF-CEM and SR cell cycle analysis. These investigations showed that compound 4f exhibited pronounced dual inhibition of both kinases PDGFRα and Aurora A with potency of 24.15 and 11.83 nM, respectively. The in vitro results were supported by molecular docking studies in order to explore its binding affinity and its key amino acids interactions. This work represents compound 4f as a promising anticancer agent against leukemia.
- El-Hussieny, Marwa,El-Sayed, Naglaa F.,Fouad, Marwa A.,Ewies, Ewies F.
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- Phosphorylation of Alkenyl and Aryl C-O Bonds via Photoredox/Nickel Dual Catalysis
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A phosphorylation of alkenyl and aryl C-O bonds at room temperature via photoredox/nickel dual catalysis is reported. By starting from easily available and inexpensive sulfonates, a variety of important alkenyl phosphonates and aryl phosphine oxides are g
- Liao, Li-Li,Gui, Yong-Yuan,Zhang, Xiao-Bo,Shen, Guo,Liu, Hui-Dong,Zhou, Wen-Jun,Li, Jing,Yu, Da-Gang
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supporting information
p. 3735 - 3738
(2017/07/26)
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- Comparative Study of the Limitations and Challenges in Atom-Transfer C-H Oxidations
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A comparative study is disclosed that seeks to highlight the current limitations and challenges that exist in the field of atom-transfer C-H oxidations. State-of-the-art methods are benchmarked in order to showcase clear differences and similarities. A novel Mn-mediated method for C-H oxidation is disclosed that serves as a rapid and simple method for aliphatic C-H hydroxylation. Finally, two methods that allow for C-H oxidation in the presence of pyridine-containing substrates are studied, something that is rare in the field but of great interest to the chemical community.
- Adams, Ashley M.,Du Bois,Malik, Hasnain A.
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supporting information
p. 6066 - 6069
(2016/01/09)
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- Chromatography-Free and Eco-Friendly Synthesis of Aryl Tosylates and Mesylates
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Two chromatography-free and eco-friendly protocols have been developed to synthesize aryl tosylates and mesylates by the tosylation and mesylation of the corresponding hydroxyarenes, respectively. These protocols are superior to other known ones regarding
- Lei, Xiangyang,Jalla, Anusha,Abou Shama, Mhd A.,Stafford, Jamie M.,Cao, Billy
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supporting information
p. 2578 - 2585
(2015/09/01)
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- UREA COMPOUNDS AND THEIR USE AS FAAH ENZYME INHIBITORS
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There is provided a compound having Formula I:(I) wherein: R1 is aryl which is optionally substituted with one or more groups selected from hydroxyl, halogen and C1-4 alkoxy, or R1 is aryl which is substituted with a second aryl group or an aryloxy group, wherein the second aryl group or the aryloxy group is optionally substituted with one or more groups selected from hydroxyl, halogen and C1-4 alkoxy; R2 is C1-4 alkyl; R3 is selected from hydroxyl and OSO2CH3; R4 and R5 are independently selected from hydrogen, hydroxyl and halogen; and n is 0 or 1; or a pharmaceutically acceptable salt thereof; wherein when R3 is hydroxyl and R4 and R5 are not hydroxyl, the optionally substituted aryl group, second aryl group or aryloxy group of R1 is substituted with one or more hydroxyl groups or C1-4 alkoxy groups, or wherein when R3 is hydroxyl, one of R4 and R5 is hydroxyl, provided that the compound is not N-(1-benzylpiperidin-4-yl)-4-(3,4-dihydroxyphenyl)-N-methyl-1H-imidazole-1-carboxamide hydrobromide. The compound may be used as an inhibitor of fatty acid amide hydrolase.
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Page/Page column 32-33
(2015/02/25)
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- Cyanation of unactivated aryl chlorides and aryl mesylates catalyzed by palladium and hemilabile MOP-type ligands
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Palladium-catalyzed cyanation of aryl halides and pseudo halides with potassium hexacyanoferrate is described employing the hemilabile, bulky, and electron-rich MOP-type ligands. When the mixture of t-BuOH and H2O was used as the solvent and K2CO3 as the base, the MOP-type ligands showed high efficiency for the palladium-catalyzed cyanation. The effect of ligand structure was studied in detail, and 2-di-tert-butylphosphino-2′-isopropoxy-1,1′-binaphthyl was the more effective for the cyanation. The catalyst system allows the cyanation of unactivated aryl chlorides, and even aryl mesylates to occur in good yields. Furthermore, the reactivity of different arylated reagents in the catalytic system was found to be: ArBr > ArCl >> ArOMs > ArOSO2Im > ArOSO2NMe2.
- Tu, Yahui,Zhang, Yi,Xu, Sheng,Zhang, Zhaoguo,Xie, Xiaomin
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supporting information
p. 2938 - 2942
(2015/01/16)
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- A general palladium catalyst system for suzuki-miyaura coupling of potassium aryltrifluoroborates and aryl mesylates
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(Figure presented) The first general examples of palladium-catalyzed Suzuki-type cross-coupling of aryl and heteroaryl mesylates with potassium aryl and heteroaryltrifluoroborates are presented. In addition to biaryl couplings, the cross-coupling reactions of aryl mesylates with alkyl and vinyltrifluoroborate salts have also been successfully accomplished.
- Chow, Wing Kin,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 5109 - 5112
(2010/09/05)
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- A mild and efficient palladium-catalyzed cyanation of aryl mesylates in water or tBuOH/water
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Cool and compatible: Aryl mesylates and tosylates underwent palladium-catalyzed cyanation under mild, aqueous conditions at 65-80°C (see scheme). In many cases, water could be used as the reaction medium without a cosolvent, and a variety of substituents R, such as keto, aldehyde, ester, free amine, and nitrile groups, remained intact during the transformation. Cy=cyclohexyl, Ms=methanesulfonyl, Ts=p-toluenesulfonyl.
- Yeung, Pui Yee,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 8918 - 8922
(2011/02/24)
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- Pitfalls in assessing the α-effect: Reactions of substituted phenyl methanesulfonates with HOO-, OH-, and substituted phenoxides in H2O
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Toward resolving the current controversy regarding the validity of the α-effect, we have examined the reactions of Y-substituted phenyl methanesulfonates 1a-1l with HOO-, OH-, and Z-substituted phenoxides in the gas phase versus solu
- Um, Ik-Hwan,Im, Li-Ra,Buncel, Erwin
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body text
p. 8571 - 8577
(2011/03/20)
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- N-heterocyclic carbene derived Nickel-Pincer complexes: Efficient and applicable catalysts for Suzuki-Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates
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Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to- sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates).
- Kuroda, Jun-Ichi,Inamoto, Kiyofumi,Hiroya, Kou,Doi, Takayuki
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experimental part
p. 2251 - 2261
(2009/08/09)
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- Palladium-indolylphosphine-catalyzed hiyama cross-coupling of aryl mesylates
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(Chemical Equation Presented) Aryl mesylates are found to be applicable as electrophiles in organosilicon-mediated coupling reactions. The catalyst system comprising 2 mol % of Pd(OAc)2 and CM-phos supporting ligand is highly effective in catalyzing Hiyama cross-coupling of various aryl and heteroaryl mesylates. Interesting acid additive effects show that the presence of 0.25-0.50 equiv of acetic acid efficiently suppresses the mesylate decomposition and generally promotes the coupling product yields.
- So, Chau Ming,Lee, Hang Wai,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 317 - 320
(2009/07/04)
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- A general palladium-catalyzed Suzuki-Miyaura coupling of aryl mesylates
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(Chemical Equation Presented) Catalyze this! The first palladium-catalyzed Suzuki-Miyaura coupling of unactivated aryl mesylates is reported, with not only arylboronic acids, but also other organoboron nucleophiles (see picture; Z=B(OH)2, BF3K, BPin). The reaction conditions are compatible with various common functional groups (R1=alkyl, OMe, CHO, CO, CN, CO2R′, heteroaryl).
- So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 8059 - 8063
(2009/04/13)
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- 2,2′-bipyridine: An efficient ligand in the cobalt-catalyzed synthesis of organozinc reagents from aryl chlorides and sulfonates
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The synthesis of functionalized arylzinc reagents from aromatic chlorides, triflates, or mesylates, via cobalt catalysis, is reported using 2,2′-bipyridine as a ligand in a mixture of acetonitrile and pyridine. This procedure allows the synthesis of a variety of functionalized arylzinc species in good to excellent yields. Some of these arylzinc compounds have been coupled with aromatic bromides under palladium catalysis. Georg Thieme Verlag Stuttgart.
- Kazmierski, Igor,Gosmini, Corinne,Paris, Jean-Marc,Périchon, Jacques
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p. 881 - 884
(2007/10/03)
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- NiCl2(dppe)-Catalyzed Cross-Coupling of Aryl Mesylates, Arenesulfonates, and Halides with Arylboronic Acids
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An investigation of the NiCl2(dppe)-, NiCl2(dppb)-, NiCl2(dppf)-, NiCl2(PCy3)2-, and NiCl2(PPh3)2- catalyzed cross-coupling of the previously unreported aryl mesylates, and of aryl arenesulfonates, chlorides, bromides, and iodides containing electron-withdrawing and electron-donating substituents with aryl boronic acids, in the absence of a reducing agent, is reported. NiCl2(dppe) was the only catalyst that exhibited high and solvent-independent activity in the two solvents investigated, toluene and dioxane. NiCl2(dppe) with an excess of dppe, NiCl 2(dppe)/dppe, was reactive in the cross-coupling of electron-poor aryl mesylates, tosylates, chlorides, bromides, and iodides. This catalyst was also efficient in the cross-coupling of aryl bromides and iodides containing electron-donating substituents. Most surprisingly, the replacement of the excess dppe from NiCl2(dppe)/dppe with excess PPh3 generated NiCl2(dppe)/PPh3, which was found to be reactive for the cross-coupling of both electron-rich and electron-poor aryl mesylates and chlorides. Therefore, the solvent-independent reactivity of NiCl2(dppe) provides an inexpensive and general nickel catalyst for the cross-coupling of aryl mesylates, tosylates, chlorides, bromides, and iodides with aryl boronic acids.
- Percec, Virgil,Golding, Geoffrey M.,Smidrkal, Jan,Weichold, Oliver
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p. 3447 - 3452
(2007/10/03)
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- Scope and limitation of the nickel-catalyzed coupling reaction between lithium borates and mesylates
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Coupling reaction of aryl borates and mesylates derived from phenols and enols was studied. Mesylates with an electron-with-drawing group or ring were highly reactive at room temperature in the presence of NiCl2(PPh3)2 to furnish the coupling products in good yields.
- Kobayashi, Yuichi,William, Anthony D.,Mizojiri, Ryo
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- Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates
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Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ.This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls.The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated.In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.
- Percec, Virgil,Bae, Jin-Young,Zhao, Mingyang,Hill, Dale H.
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p. 176 - 185
(2007/10/02)
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- Acid-Catalyzed Thermal Decomposition of 1-Aryl-3,3-dialkyltriazenes in the Presence of Nucleophiles
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The acid-catalyzed thermal decompositions of a number of 1-aryl-3,3-dialkyltriazenes (1) in the presence of nucleophiles have been conducted with a view to understanding the underlying mechanisms of these reactions.These reactions parallel the corresponding diazonium ion reactions in that a heterolytic dediazoniation path competes with a homolytic route.The relative proportion of the products arising due to these two competing mechanisms depends upon (a) the electron-transfer efficiency of the nucleophile, (b) the redox potential of the aryl diazonium substrate, and (c) the reaction solvent.
- Satyamurthy, N.,Barrio, Jorge R.,Schmidt, Derrick G.,Kammerer, Craig,Bida, Gerald T.,Phelps, Michael E.
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p. 4560 - 4564
(2007/10/02)
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- ALKANESULFONYLATION REACTIONS IX. CATALYTIC EFFECT OF PYRIDINES ON THE MESYLATION OF PHENOLS
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The kinetics of the mesylation of seven substituted phenols in the presence of 13 derivatives of pyridine in benzene at 50 deg C were investigated.It was shown that in this case, in contrast to catalysis by trialkylamines, the elimination-addition (sulfen
- Skrypnik, Yu. G.,Bezrodnyi, V. P.
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p. 2056 - 2063
(2007/10/02)
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