- One-pot cyclization of 2-aminophenethyl alcohols: A novel and direct approach to the synthesis of N-acyl indolines
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(Chemical Equation Presented) A unique one-pot cyclization of 2-aminophenethyl alcohols with carboxylic acids in the presence of PPh 3, CCL4, and NEt3 furnished the formation of N-acyl indolines in good to excellent yields. This new approach provides an efficient, scalable, low-cost, and direct access to the biologically important indolines which are further oxidizable to indoles and oxindoles.
- Wang, Zengxue,Wan, Wen,Jiang, Haizhen,Hao, Jian
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Read Online
- Electrochemical approach to trifluoroacetamide synthesis from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) catalyzed by B12complex
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One-pot synthetic approach to produce trifluoroacetamide has been developed using an electrochemical method with the B12 complex as a catalyst under mild conditions, in open air at room temperature. Thirty examples of trifluoroacetamide were synthesized from 1,1,1-trichloro-2,2,2-trifluoroethane (CFC-113a) in moderate to good yields. This user-friendly strategy is compatible with a broad range of trifluoroacetamide syntheses.
- Moniruzzaman, Mohammad,Yano, Yoshio,Ono, Toshikazu,Hisaeda, Yoshio,Shimakoshi, Hisashi
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- Redox-Neutral Coupling between Two C(sp3)?H Bonds Enabled by 1,4-Palladium Shift for the Synthesis of Fused Heterocycles
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The intramolecular coupling of two C(sp3)?H bonds to forge a C(sp3)?C(sp3) bond is enabled by 1,4-Pd shift from a trisubstituted aryl bromide. Contrary to most C(sp3)?C(sp3) cross-dehydrogenative couplings, this reaction operates under redox-neutral conditions, with the C?Br bond acting as an internal oxidant. Furthermore, it allows the coupling between two moderately acidic primary or secondary C?H bonds, which are adjacent to an oxygen or nitrogen atom on one side, and benzylic or adjacent to a carbonyl group on the other side. A variety of valuable fused heterocycles were obtained from easily accessible ortho-bromophenol and aniline precursors. The second C?H bond cleavage was successfully replaced with carbonyl insertion to generate other types of C(sp3)-C(sp3) bonds.
- Rocaboy, Ronan,Anastasiou, Ioannis,Baudoin, Olivier
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supporting information
p. 14625 - 14628
(2019/09/16)
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- Discovery and Characterization of CD12681, a Potent RORγ Inverse Agonist, Preclinical Candidate for the Topical Treatment of Psoriasis
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With possible implications in multiple autoimmune diseases, the retinoic acid receptor-related orphan receptor RORγ has become a sought-after target in the pharmaceutical industry. Herein are described the efforts to identify a potent RORγ inverse agonist compatible with topical application for the treatment of skin diseases. These efforts culminated in the discovery of N-(2,4-dimethylphenyl)-N-isobutyl-2-oxo-1-[(tetrahydro-2H-pyran-4-yl)methyl]-2,3-dihydro-1H-benzo[d]imidazole-5-sulfonamide (CD12681), a potent inverse agonist with in vivo activity in an IL-23-induced mouse skin inflammation model.
- Ouvry, Gilles,Atrux-Tallau, Nicolas,Bihl, Franck,Bondu, Aline,Bouix-Peter, Claire,Carlavan, Isabelle,Christin, Olivier,Cuadrado, Marie-Josée,Defoin-Platel, Claire,Deret, Sophie,Duvert, Denis,Feret, Christophe,Forissier, Mathieu,Fournier, Jean-Fran?ois,Froude, David,Hacini-Rachinel, Fériel,Harris, Craig Steven,Hervouet, Catherine,Huguet, Hélène,Lafitte, Guillaume,Luzy, Anne-Pascale,Musicki, Branislav,Orfila, Danielle,Ozello, Benjamin,Pascau, Coralie,Pascau, Jonathan,Parnet, Véronique,Peluchon, Guillaume,Pierre, Romain,Piwnica, David,Raffin, Catherine,Rossio, Patricia,Spiesse, Delphine,Taquet, Nathalie,Thoreau, Etienne,Vatinel, Rodolphe,Vial, Emmanuel,Hennequin, Laurent Fran?ois
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supporting information
p. 321 - 337
(2018/02/12)
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- MULTIVALENT RAS BINDING COMPOUNDS
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Described herein are compounds that modulate Ras signaling, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in the treatment of conditions, diseases, or disorders associated with altered Ras signaling. Further described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds and methods of using such compounds in the treatment of cell proliferative disorders, including cancer.
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Paragraph 00852
(2017/07/23)
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- A class of sulfonamide carbonic anhydrase inhibitors with neuropathic pain modulating effects
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A series of benzene sulfonamide carbonic anhydrase (CA, EC 4.2.1.1) inhibitors which incorporate lipophilic 4-alkoxy- and 4-aryloxy moieties, together with several derivatives of ethoxzolamide and sulfanilamide are reported. These derivatives were investi
- Carta, Fabrizio,Di Cesare Mannelli, Lorenzo,Pinard, Melissa,Ghelardini, Carla,Scozzafava, Andrea,McKenna, Robert,Supuran, Claudiu T.
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p. 1828 - 1840
(2015/03/14)
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- BORON-CONTAINING SMALL MOLECULES
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This invention relates to 6-substituted benzoxaborole compounds of the following formula and their use for treating bacterial infections.
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Page/Page column 129
(2011/06/16)
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- INDOLINE SCAFFOLD SHP-2 INHIBITORS AND CANCER TREATMENT METHOD
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The subject invention concerns methods and compounds for inhibiting Shp2. In one embodiment, a compound of the invention has a chemical structure as shown in formula I or II: wherein X, Y, and Z are independently N or S; R1 is cycloalkyl, heter
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Page/Page column 55-56
(2010/04/03)
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- PYRIMIDINE SULFONAMIDE ANALOGS AND THEIR USE AS AGONISTS OF THE WNT-BETA-CATENIN CELLULAR MESSAGING SYSTEM
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The present invention relates to pyrimidine sulfonamide analogs, methods of making pyrimidine sulfonamide analogs, compositions comprising a pyrimidine sulfonamide analog, and methods for treating canonical Wnt-β-catenin cellular messaging system-related disorders comprising administering to a subject in need thereof an effective amount of a pyrimidine sulfonamide analog.
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Page/Page column 17
(2009/03/07)
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- Pd(II)-catalyzed amination of C-H bonds using single-electron or two-electron oxidants
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(Chemical Equation Presented) Pd(II)-catalyzed intramolecular amination of arenes is developed using either a one- or two-electron oxidant. The reaction protocol tolerates a wide range of deactivating groups including acetyl, cyano, and nitro groups. This catalytic reaction allows expedient syntheses of broadly useful substituted indolines or indoles.
- Mei, Tian-Sheng,Wang, Xisheng,Yu, Jin-Quan
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supporting information; experimental part
p. 10806 - 10807
(2009/12/04)
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- MACROLONE COMPOUNDS
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A compound of formula (I) compositions comprising same, processes for their preparation and use of said compounds, particularly in the treatment of microbial infections.
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Page/Page column 44-45
(2008/06/13)
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- Optimization of the indolyl quinolinone class of KDR (VEGFR-2) kinase inhibitors: Effects of 5-amido- and 5-sulphonamido-indolyl groups on pharmacokinetics and hERG binding
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Modifications to the basic side-chain of early lead structures of the indolyl quinolinone class of KDR kinase inhibitors resulted in improved pharmacokinetic and ancillary profiles. Specifically, compounds bearing 5-amido- and 5-sulphonamido-indolyl substituents exhibited lower plasma clearance and weaker binding affinity for the IKr potassium channel hERG. 2003 Elsevier Science Ltd. All rights reserved.
- Fraley, Mark E.,Arrington, Kenneth L.,Buser, Carolyn A.,Ciecko, Patrice A.,Coll, Kathleen E.,Fernandes, Christine,Hartman, George D.,Hoffman, William F.,Lynch, Joseph J.,McFall, Rosemary C.,Rickert, Keith,Singh, Romi,Smith, Sheri,Thomas, Kenneth A.,Wong, Bradley K.
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p. 351 - 355
(2007/10/03)
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- Novel diarylsulfonylurea derivatives as potent antimitotic agents
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Novel diarylsulfonylurea derivatives have been synthesized and identified as potent inhibitors of tubulin polymerization and cancer cell proliferation. Furthermore, these compounds were also efficacious against multidrug-resistant cancer cells. A novel series of diarylsulfonylurea derivatives were synthesized and evaluated for interaction with tubulin and for cytotoxicity against human cancer cell lines. These derivatives demonstrated good inhibitory activity against tubulin polymerization, which was well correlated with promising antiproliferative activity as well as G2/M phase cell cycle arrest. Furthermore, several compounds were also efficacious against multidrug-resistant cancer cells, which are resistant to many other known microtubule inhibitors.
- Kim, Semi,Park, Ji Hyun,Koo, Sun-Young,Kim, Jung In,Kim, Min-Hyeung,Kim, Ji Eun,Jo, Kiwon,Geun Choi, Hwan,Lee, Sung Bae,Jung, Sang-Hun
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p. 6075 - 6078
(2007/10/03)
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- ON THE REACTION OF INDOLE WITH SODIUM BOROHYDRIDE IN TRIFLUOROACETIC ACID
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The reaction of indole (1) with sodium borohydride in trifluoroacetic acid gives, successively, indoline (3), N-(2,2,2-trifluoroethyl)indoline (4), and 1,1,1-trifluoro-2,2-bisethane (5), whose structure is established by chemical and spectral means.Similar reactions are observed with N-methylaniline (8) and anisole, but not with dibenzazepines 13 and 15, which give only N-trifluoroethylation.
- Gribble, Gordon W.,Nutaitis, Charles F.,Leese, Robert M.
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p. 379 - 386
(2007/10/02)
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