- Direct preparation of polyfunctional amino-substituted arylmagnesium reagents via an iodine-magnesium exchange reaction
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The successive addition of PhMgCl and i-PrMgCl to functionalised iodoanilines allows their conversion to the corresponding amino-functionalised Grignard reagents, which react smoothly with a range of electrophiles in high yield.
- Varchi, Greta,Kofink, Christiane,Lindsay, David M.,Ricci, Alfredo,Knochel, Paul
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Read Online
- Amidino substituted 2-aminophenols: biologically important building blocks for the amidino-functionalization of 2-substituted benzoxazoles
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Unlike the closely related and widely investigated amidino-substituted benzimidazoles and benzothiazoles with a range of demonstrated biological activities, the matching benzoxazole analogues still remain a largely understudied and not systematically evaluated class of compounds. To address this challenge, we utilized the Pinner reaction to convert isomeric cyano-substituted 2-aminophenols into their amidine derivatives, which were isolated as hydrochlorides and/or zwitterions, and whose structure was confirmed by single crystal X-ray diffraction. The key step during the Pinner synthesis of the crucial carboximidate intermediates was characterized through mechanistic DFT calculations, with the obtained kinetic and thermodynamic parameters indicating full agreement with the experimental observations. The obtained amidines were subjected to a condensation reaction with aryl carboxylic acids that allowed the synthesis of a new library of 5- and 6-amidino substituted 2-arylbenzoxazoles. Their antiproliferative features against four human tumour cell lines (SW620, HepG2, CFPAC-1, HeLa) revealed sub-micromolar activities on SW620 for several cyclic amidino 2-naphthyl benzoxazoles, thus demonstrating the usefulness of the proposed synthetic strategy and promoting amidino substituted 2-aminophenols as important building blocks towards biologically active systems.
- Pti?ek, Lucija,Hok, Lucija,Grb?i?, Petra,Topi?, Filip,Cetina, Mario,Rissanen, Kari,Paveli?, Sandra Kraljevi?,Vianello, Robert,Racané, Livio
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supporting information
p. 2784 - 2793
(2021/04/07)
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- High-Density and Thermally Stable Palladium Single-Atom Catalysts for Chemoselective Hydrogenations
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Single-atom catalysts (SACs) have shown superior activity and/or selectivity for many energy- and environment-related reactions, but their stability at high site density and under reducing atmosphere remains unresolved. Herein, we elucidate the intrinsic driving force of a Pd single atom with high site density (up to 5 wt %) under reducing atmosphere, and its unique catalytic performance for hydrogenation reactions. In situ experiments and calculations reveal that Pd atoms tend to migrate into the surface vacancy-enriched MoC surface during the carburization process by transferring oxide crystals to carbide crystals, leading to the surface enrichment of atomic Pd instead of formation of particles. The Pd1/α-MoC catalyst exhibits high activity and excellent selectivity for liquid-phase hydrogenation of substituted nitroaromatics (>99 %) and gas-phase hydrogenation of CO2 to CO (>98 %). The Pd1/α-MoC catalyst could endure up to 400 °C without any observable aggregation of single atoms.
- Baaziz, Walid,Chu, Wei,Ersen, Ovidiu,Greiner, Mark,Liu, Wei,Liu, Yuefeng,Ma, Ying,Pham-Huu, Cuong,Ren, Yujing,Wang, Aiqin,Zhang, Tao,Zhou, Yanan
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supporting information
p. 21613 - 21619
(2020/09/21)
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- ANTIBIOTIC COMPOUNDS
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The present invention relates to antibiotic compounds of formula (I), to compositions containing these compounds and to methods of treating bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Gram-positive and/or Gram-negative bacteria, and in particular in the treatment of infection with, and diseases caused by, Neisseria gonorrhoeae.
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Page/Page column 77; 78
(2018/03/25)
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- CONDENSED HETEROCYCLIC COMPOUND
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A compound represented by the general formula (I) [R1 represents a C1-6 alkyl group, a halogen atom, or the like; A represents a phenylene group, or the like; X represents —CH(R3)—, —O—, —NH—, or the like; Y represents —O—, —NH—, —N═, or —S—; . . . represents a single bond or double bond; n represents 1 to 3; R2 represents a C1-6 alkyl group, a C1-6 alkoxy group, or the like; and R3 represents hydrogen atom, a C1-6 alkyl group, or the like], or a salt thereof which has a blood LDL cholesterol-reducing action, and is useful as an active ingredient of medicaments.
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Paragraph 0307; 0310; 0311
(2017/11/08)
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- Diastereo- and enantioselective Pd(II)-catalyzed additions of 2-alkylazaarenes to N -boc imines and nitroalkenes
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A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.
- Best, Daniel,Kujawa, Szymon,Lam, Hon Wai
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supporting information
p. 18193 - 18196
(2013/01/15)
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- Evaluation of Potent and Selective Small-Molecule Antagonists for the CXCR2 Chemokine Receptor
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N,N′-Diarylureas were prepared, and the structure-activity relationship relative to the CXCR2 receptor was examined. This led to the identification of a potent and highly selective CXCR2 antagonist, which in addition was shown to be functionally active bo
- Widdowson, Katherine L.,Elliott, John D.,Veber, Daniel F.,Nie, Hong,Rutledge, Melvin C.,McCleland, Brent W.,Xiang, Jia-Ning,Jurewicz, Anthony J.,Hertzberg, Robert P.,Foley, James J.,Griswold, Don E.,Martin, Lenox,Lee, Judithann M.,White, John R.,Sarau, Henry M.
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p. 1319 - 1321
(2007/10/03)
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- IL-8 receptor antagonists
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The invention relates to the use of guanidine compounds in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).
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- Amidino benzimidazole inhibitors of bacterial two-component systems
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Amidino benzimidazoles have been identified as inhibitors of the bacterial KinA/Spo0F two-component system (TCS). Many of these inhibitors exhibit good in vitro antibacterial activity against a variety of susceptible and resistant Gram-positive organisms.
- Weidner-Wells, Michele A.,Ohemeng, Kwasi A.,Nguyen, Van N.,Fraga-Spano, Stephanie,Macielag, Mark J.,Werblood, Harvey M.,Foleno, Barbara D.,Webb, Glenda C.,Barrett, John F.,Hlasta, Dennis J.
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p. 1545 - 1548
(2007/10/03)
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- IL-8 RECEPTOR ANTAGONISTS
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Novel IL-8 receptor antagonists and methods of using them are provided.
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- IL-8 RECEPTOR ANTAGONISTS
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The present invention relates to novel compounds and a novel use of phenyl ureas in the treatment of disease states mediated by the chemokine Interleukin-8 (IL-8).
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- A new intramolecular migration of the imino group of O-arylketoximes to the aryl group under the Beckmann condition
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ZrCl4-mediated decomposition of O-arylketoximes in benzene leads to regioselective intramolecular migration of the imino group from the oxygen to the ortho position of the aryl group via electron-deficient nitrogen intermediates.
- Kikugawa, Yasuo,Tsuji, Chiho,Miyazawa, Etsuko,Sakamoto, Takeshi
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p. 2337 - 2339
(2007/10/03)
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- IL-8 RECEPTOR ANTAGONISTS
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This invention relates to the novel use of phenyl ureas in the treatment of disease states mediated by the chemokine, Interleukin-8 (IL-8).
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- Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones
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The compound of the formula: STR1 wherein R1 is straight chain alkyl, branched chain alkyl, cycloalkyl, hydroxyalkyl, fluoroalkyl, or polyfluoroalkyl; and one of R2, R3 and R4 is hydroxyl and the other two are,
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- IL-8 RECEPTOR ANTAGONISTS
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This invention relates to novel compounds and a novel use of phenyl ureas in the treatment of disease scates mediated by the chemokine, Interleukin-8 (IL-8). In particular, this invention relates to the novel compounds of Formula (Ia) and their use in treating chemokine mediated diseases wherein the chemokine binds to an IL-8 a or b receptor. Compounds of Formula (Ia) are represented by the structure: STR1 wherein interalia, X is oxygen or sulfur;Rb is NR 6 R. sub.7, alkcyl, aryl, arylC 1-4 alkyl, aryl C 2-4 alkenyl, heteroaryl, heteroarylC 1-4 alkyl, heteroarylC 2-4 alkenyl, heterocyclic or heterocyclic C 1-4 alkyl, or a heterocyclic C 2-4 alkenyl moiety, camphor, all of which may be optionally substituted; R 1 is independently selected from hydrogen; halogen; nitro; cyano; C 1-10 alkyl; halosubstituted C 1-10 alkyl; C 2-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR. sub.8 R 8)q S(O) t R 4 ; hydroxy; hydroxy substituted C 1-4 alkyl; aryl; aryl C 1-4 alkyl; aryl C 2-10 alkenyl; aryloxy; aryl C 1-4 alkyloxy; heteroaryl; heteroarylalkyl; heteroaryl C 2-10 alkenyl; heteroaryl C 1-4 alkyloxy; heterocyclic; heterocyclic C 1-4 alkyl; heterocyclicC 1-4 alkyloxy; heterocyclic C 2-10 alkenyl; q is 0 or an integer having a value of 1 to 10; n is an integer having a value of 1 to 3;m is an integer having a value of 1 to 3; Y is hydrogen; halogen; nitro; cyano; halosubstituted C 1-10 alkyl; C 1-10 alkyl; C 2-10 alkenyl C. sub.1-10 alkoxy; halosubstituted C 1-10 alkoxy; azide; (CR 8 R. sub.8)qS(O) t R 4, (CR 8 R 8)qOR 4 ; hydorxy; hydroxy substituted C. sub.1-4 alkyl; aryl; aryl C 1-4 alkyl; aryloxy; arylC. sub.1-4 alkyloxy; aryl C 2-10 alkenyl; heteroaryl; heteroarylalkyl; heteroaryl C 1-4 alkyloxy; heteroaryl C 2-10 alkenyl; heterocyclic, heterocyclic C 1-4 alkyl; heterocyclicC 2-10 alkenyl;or a pharmaceutically acceptable salt thereof.
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