- Annulations via dianions: Formation of five-, six- and seven-membered rings
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Phosphonium salts bearing an electron-withdrawing group at the γ-position form dianions that react with bis-electrophiles to generate five-, six-, and seven- membered rings.
- Kraus, George A.,Kesavan, Sarathy
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Read Online
- Phosphatidylcholine bearing 6,6-dideuterated oleic acid: A useful solid-state 2H NMR probe for investigating membrane properties
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Lipid organization has been at the center of research on lipid rafts. Dioleoylphosphatidylcholine (DOPC) is a typical unsaturated lipid. Very few studies have reported its thermodynamics in raft-like membranes. Herein, we have developed a highly efficient
- Cui, Jin,Lethu, Sébastien,Yasuda, Tomokazu,Matsuoka, Shigeru,Matsumori, Nobuaki,Sato, Fuminori,Murata, Michio
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Read Online
- Sulfonamide hapten, sulfonamide artificial antigen and their preparation methods and application
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The invention relates to a sulfonamide hapten, a sulfonamide artificial antigen and their preparation methods and application. The sulfonamide hapten has a structure shown as formula (1) which is shown in the description, wherein n is an integer equal to 0, or greater than and equal to 1. The sulfonamide artificial antigen is made by coupling the hapten of the formula (1) and a carrier protein. Byimmunizing animals with the sulfonamide artificial antigen, specific antibodies with high efficacy and high sensitivity can be attained. The sulfonamide hapten and antibodies prepared with the same help provide a new means to establish a method to detect sulfonamides under high speed, good simplicity, low cost, good sensitivity and good specificity.
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Paragraph 0071; 0072
(2019/06/30)
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- Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization
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Asymmetric Prins cyclization of in situ generated quinone methides and o-aminobenzaldehyde has been developed with chiral phosphoric acid as an efficient catalyst. This unconventional method provides a facile access to diverse functionalized trans-fused pyrano-/furo-tetrahydroquinoline derivatives in excellent yield and with excellent diastereo- and enantioselectivities (up to 99% yield and 99% ee). Mechanistic studies suggested that the three adjacent tertiary stereocenters were constructed through the sequential formation of C-O, C-C, and C-N bonds.
- Sun, Huai-Ri,Zhao, Qingyang,Yang, Hui,Yang, Sen,Gou, Bo-Bo,Chen, Jie,Zhou, Ling
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supporting information
p. 7143 - 7148
(2019/09/07)
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- Synthesis of 1-Acyl-2-vinylcyclopropanes: Utilizing Copper-Carbenoid versus Sulfur Ylide Methodology
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The synthesis of a range of racemic 1-acyl-2-vinylcyclopropanes by using two different methodologies is studied. We have developed a copper-catalyzed process for converting diazoketones into 1-acyl-2-vinylcyclopropanes and a sulfur-ylide-mediated procedur
- Zens, Anna,Seubert, Philipp,Kolb, Benedikt,Wurster, Marius,Holzwarth, Marcel,Mannchen, Fabian,Forschner, Robert,Claasen, Birgit,Kunz, Doris,Laschat, Sabine
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p. 2367 - 2384
(2018/04/05)
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- Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers
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Alkene hydroarylation forms carbon-carbon bonds between two foundational building blocks of organic chemistry: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel-Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings.
- Green, Samantha A.,Vásquez-Céspedes, Suhelen,Shenvi, Ryan A.
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supporting information
p. 11317 - 11324
(2018/09/18)
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- Dirhodium(II)-Mediated Alkene Epoxidation with Iodine(III) Oxidants
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Dirhodium(II) complexes and iodine(III) oxidants have found useful applications in synthetic nitrene chemistry. In this study, the combination of the dirhodium(II) complex Rh2(tpa)4 (tpa = triphenylacetate) with the iodine(III) oxidant PhI(OPiv)2 is shown to promote the epoxidation of alkenes in the presence of 2 equivalents of water. The reaction can be applied to diversely substituted alkenes and the corresponding epoxides are isolated with yields of up to 90 %. A possible mechanism involves the dirhodium(II) complex as a Lewis acid species that would tune the oxidizing character of the iodine(III) reagent.
- Nasrallah, Ali,Grelier, Gwendal,Lapuh, Maria Ivana,Duran, Fernando J.,Darses, Benjamin,Dauban, Philippe
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supporting information
p. 5836 - 5842
(2018/11/24)
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- trans-Cyclooctenes as Halolactonization Catalysts
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The strained olefins in trans-cyclooctenes serve as efficient catalysts for halolactonizations, including bromolactonizations and iodolactonizations. The trans-cyclooctene framework is essential for excellent catalytic performance, and the substituents also play important roles in determining efficiency. These results are the first demonstration of catalysis by a trans-cyclooctene.
- Einaru, Shunsuke,Shitamichi, Kenta,Nagano, Tagui,Matsumoto, Akira,Asano, Keisuke,Matsubara, Seijiro
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supporting information
p. 13863 - 13867
(2018/09/27)
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- The compound, composition, and display device
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PROBLEM TO BE SOLVED: To provide a compound capable of elevating an upper limit temperature where a SmC (smectic-C) phase of a liquid crystal can exist, broadening a temperature width of the SmC phase or enlarging a tilt angle of the SmC phase, and to provide a liquid crystal composition comprising the compound and a display element including the liquid crystal composition.SOLUTION: [1] The compound is expressed by general formula (i) shown below. In general formula (i), R and R' each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 9 carbon atoms; A1, A2 and A3 each independently represent a 1,4-phenylene group or a 2,3-difluoro-1,4-phenylene group; m represents an integer of 1 to 10; and Y represents a cyclohexylene group, a phenylene group, a bicyclooctylene group or a dialkylsilylene group.
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Paragraph 0198-0200
(2017/07/26)
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- NOVEL CYCLOSPORIN DERIVATIVES AND USES THEREOF
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A compound of the Formula (I) is disclosed: (I) or pharmaceutically acceptable salt thereof, wherein the symbols are as defined in the specification. Also described are a pharmaceutical composition comprising the same and a method for treating or preventing viral infections, inflammation, dry eye, central nervous disorders, cardiovascular diseases, cancer, obesity, diabetes, muscular dystrophy, lung, and liver, and kindey diseases, and hair loss using the same.
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Paragraph 0216
(2017/12/18)
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- Novel multifunctional dopamine D2/D3receptors agonists with potential neuroprotection and anti-alpha synuclein protein aggregation properties
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Our ongoing drug development endeavor to design compounds for symptomatic and neuroprotective treatment of Parkinson's disease (PD) led us to carry out a structure activity relationship study based on dopamine agonists pramipexole and 5-OHDPAT. Our goal was to incorporate structural elements in these agonists in a way to preserve their agonist activity while producing inhibitory activity against aggregation of α-synuclein protein. In our design we appended various catechol and related phenol derivatives to the parent agonists via different linker lengths. Structural optimization led to development of several potent agonists among which (?)-8a, (?)-14 and (?)-20 exhibited potent neuroprotective properties in a cellular PD model involving neurotoxin 6-OHDA. The lead compounds (?)-8a and (?)-14 were able to modulate aggregation of α-synuclein protein efficiently. Finally, in an in vivo PD animal model, compound (?)-8a exhibited efficacious anti-parkinsonian effect.
- Luo, Dan,Sharma, Horrick,Yedlapudi, Deepthi,Antonio, Tamara,Reith, Maarten E.A.,Dutta, Aloke K.
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p. 5088 - 5102
(2016/10/22)
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- Total Synthesis of Prostaglandin 15d-PGJ2 and Investigation of its Effect on the Secretion of IL-6 and IL-12
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An efficient synthesis of 15-deoxy-Δ12,14-prostaglandin J2 (15d-PGJ2, 1) is reported. The route described allows for diversification of the parent structure to prepare seven analogues of 1 in which the positioning of electrophilic sites is varied. These analogues were tested in SAR studies for their ability to reduce the secretion of proinflammatory cytokines. It was shown that the endocyclic enone is crucial for the bioactivity investigated and that the conjugated ω-side chain serves in a reinforcing manner.
- Egger, Julian,Fischer, Stefan,Bretscher, Peter,Freigang, Stefan,Kopf, Manfred,Carreira, Erick M.
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supporting information
p. 4340 - 4343
(2015/09/15)
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- NEUROPROTECTIVE AGENTS FOR TREATMENT OF NEURODEGENERATIVE DISEASES
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A compound having formula I is useful for treating a neurodegenerative disease: I, R1 is an C1-12 organyl group; is a C1-12 heterocyclic ring system containing 5 to 12 ring atoms and up to three heteroatoms individually selected from the group consisting of N, O, S, and Se; R2 are C1-12 organyl groups; R7, R8 are each independently, hydrogen (H), hydroxyl, oxo (i.e., carbonyl), C1-8 alkyl, C1-8 alkoxyl, C2-8 alkenyl, C2-10 alkynyl, C5-7 cycloalkyl, C5-7 cycloalkenyl, halo, C1-4 aldehyde, or -NR4q where R4 is H, C1-8 alkyl, C2-8 alkenyl, C4-8 cycloalkyl, C4-8 cycloalkenyl, or C6-10 aryl; o is 0, 1, 2, 3, or 4; A is a C6-12 aryl group, C5-12 heteroaryl group, or an optionally substituted 3-hydroxypyridin- 4(1H)-one; p is an integer from 1 to 6; and Zm is absent or a divalent linking moiety; and m is an integer representing the number of time Z is repeated.
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Paragraph 00091; 00092; 000108; 000109
(2014/06/23)
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- Palladium(II)-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives
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A palladium-catalyzed enantio- and diastereoselective synthesis of pyrrolidine derivatives is described. Initial intramolecular nucleopalladation of the tethered protected amine forms the pyrrolidine moiety and a quinone methide intermediate. A second nucleophile adds intermolecularly to afford diverse products in high enantio- and diastereoselectivity.
- Jana, Ranjan,Pathak, Tejas P.,Jensen, Katrina H.,Sigman, Matthew S.
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supporting information; experimental part
p. 4074 - 4077
(2012/09/22)
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- Peroxisome proliferator-activated receptor agonists with phenethylphenylphthalimide skeleton derived from thalidomide-related liver X receptor antagonists: Relationship between absolute configuration and subtype selectivity
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Introduction of an alkylcarboxylic acid unit, which is a partial structure of endogenous peroxisome proliferator-activated receptor (PPAR) ligands, into a phenethylphenylphthalimide skeleton, which possesses liver X receptor (LXR) antagonistic activity, afforded novel PPAR ligands. The results of structure-activity relationship analysis and docking studies led us to the potent PPAR agonists 13c-e. The absolute configuration of 13c-e affects the PPAR subtype selectivity.
- Motoshima, Kazunori,Ishikawa, Minoru,Hashimoto, Yuichi,Sugita, Kazuyuki
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experimental part
p. 3156 - 3172
(2011/06/26)
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- Process for the synthesis of ezetimibe and intermediates useful therefor
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The present invention discloses novel and useful intermediates for the synthesis of ezetimibe (EZT), which intermediates share a characteristic Z-isomeric structure. Based on Z-5-(4-fluorophenyl)-pent-4-enoic acid, and proceeding the synthesis through further Z-intermediates, a total synthesis is presented to obtained final ezetimibe in high yields.
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Page/Page column 10-11
(2010/03/02)
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- Palladium-catalyzed enantioselective addition of two distinct nucleophiles across alkenes capable of quinone methide formation
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(Chemical Equation Presented) A sequential intramolecular-intermolecular enantioselective alkene difunctionalization reaction has been developed which is thought to proceed through Pd-catalyzed quinone methide formation. The synthesis of new chiral heterocyclic compounds with adjacent chiral centers is achieved in enantiomeric ratios up to 99:1 and diastereomeric ratios up to 10:1.
- Jensen, Katrina H.,Pathak, Tejas P.,Zhang, Yang,Sigman, Matthew S.
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supporting information; experimental part
p. 17074 - 17075
(2010/03/25)
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- Enantioselective synthesis of the R-enantiomer of the feeding deterrent (S)-ypaoamide
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(Chemical Equation Presented) The enantioselective synthesis of the R-enantiomer of the marine natural product (S)-ypaoamide (5) is reported. The synthesis features both a flexible racemization-free approach to the 5-substituted 3-pyrrolin-2-one segment,
- Chen, Jie,Huang, Pei-Qiang,Queneau, Yves
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supporting information; experimental part
p. 7457 - 7463
(2010/01/06)
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- Molecular insights into azumamide E histone deacetylases inhibitory activity
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Azumamide E, a cyclotetrapeptide isolated from the sponge Mycale izuensis, is the most powerful carboxylic acid containing natural histone deacetylase (HDAC) inhibitor known to date. In this paper, we describe design and synthesis of two stereochemical va
- Maulucci, Nakia,Chini, Maria Giovanna,Di Micco, Simone,Izzo, Irene,Cafaro, Emiddio,Russo, Adele,Gallinari, Paola,Paolini, Chantal,Nardi, Maria Chiara,Casapullo, Agostino,Riccio, Raffaele,Bifulco, Giuseppe,De Riccardis, Francesco
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p. 3007 - 3012
(2008/02/03)
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- Ortho-substituted iodobenzenes as novel organocatalysts for bromination of alkenes
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Suitably ortho-substituted iodobenzenes act as organocatalysts for the transfer of electrophilic bromine from N-bromosuccinimide to alkenes via the intermediacy of bromoiodinanes. The Royal Society of Chemistry 2006.
- Braddock, D. Christopher,Cansell, Gemma,Hermitage, Stephen A.
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p. 2483 - 2485
(2008/03/28)
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- Total synthesis of azumamides A and E
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A zoom in on azumamides (2): An efficient synthetic route for two of the newly discovered marine natural products, namely azumamides A and E, has been developed (see picture). The present synthesis was followed by determination of the stereochemical structure of the azumamides. (Chemical Equation Presented)
- Izzo, Irene,Maulucci, Nakia,Bifulco, Giuseppe,De Riccardis, Francesco
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p. 7557 - 7560
(2008/01/27)
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- Enantioselective synthesis of the dioxabicyclo[3.2.1]octane core of the zaragozic acids via intramolecular Wacker-type cyclisation reactions.
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Wacker-type cyclisation reactions provide an effective entry into the dioxabicyclo[3.2.1]octane core of the zaragozic acid analogues.
- Perlmutter, Patrick,Selajerern, Walailak,Vounatsos, Filisaty
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p. 2220 - 2228
(2007/10/03)
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- Substituted imidazoles as dual histamine H1 and H3 agonists or antagonists
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The present invention discloses novel substituted imidazole compounds which have H3 receptor antagonist activity or dual histamine-H1 and H3 receptor antagonist activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such imidazoles as well as methods of using them to treat allergy, congestion, inflammatory and CNS-related diseases and others.
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- Substituted imidazoles as dual histamine H1 and H3 agonists or antagonists
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The present invention discloses novel substituted imidazole compounds which have H3 receptor antagonist or dual histamine-H1 and H3 receptor antagonist activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such imidazoles as well as methods of using them to treat allergy, nasal congestion, inflammatory and CNS-related diseases and others.
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- Predicting the diastereoselectivity of Rh-mediated intramolecular C-H insertion
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Rhodium-mediated cyclization of the α-diazo ester 1 proceeds with high diastereoselectivity, to give the trisubstituted cyclopentane 5. A computational model (ZINDO and Molecular Mechanics) based on our current mechanistic understanding of the reaction is presented. This model correctly predicts the dominant diastereomer from the cyclization of 1 and the eight (Table 2) other α-diazo esters studied thus far.
- Taber, Douglass F.,You, Kamfia K.,Rheingold, Arnold L.
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p. 547 - 556
(2007/10/03)
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- Exploration of the effects of linker chain modifications on anti-HIV activities in a series of cosaIane analogues
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The effects of linker chain modifications were investigated in a series of cosalane analogues. The modifications investigated included: (1) shortening the three-carbon linker chain between the dichlorodisalicylmethane and the cholestane moiety by one carbon atom; (2) lengthening the linker chain by one carbon; (3) hydrogenation of the double bond in the linker chain; (4) changing the point of attachment of the linker chain from C-3 to C-6; (5) insertion of a phosphate between the steroid and the linker chain. With the exception of the phosphate modification, which abolished anti-HIV activity and increased cytotoxicity, the linker chain modifications produced relatively minor changes in anti-HIV potency. The steroid and attached linker chain of cosalane therefore appear only to provide a general lipophilic appendage for the dichlorodisalicylmethane pharmacophore.
- Golebiewski, W. Marek,Keyes, Robert F.,Cushman, Mark
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p. 1637 - 1648
(2007/10/03)
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- Total synthesis of the phenalenone diterpene salvilenone
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The application of a photochemical aromatic annulation strategy in a highly efficient total synthesis of the phenalenone diterpene salvilenone is reported. The pivotal step in the synthesis involves the assembly of the key dihydrophenalene 29 in one step
- Danheiser, Rick L.,Helgason, Anna L.
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p. 9471 - 9479
(2007/10/02)
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- Studies related to fatty acid desaturation. Part I: Preparation of methyl-substituted nonanols, nonyl bromides and total synthesis of new branched oleic acids
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Convenient pathways for the synthesis of seven structurally defined isomers of methyl-nonanols and methyl-nonylbromides are described.These synthons are used to perform Wittig reactions between convenient phosphoranes and aldehydes in order to obtain seven new octadecenoic acids bearing a methyl grouping on carbons 11 to 17. branched nonan-1-ols / branched 1-nonylbromides / Wittig reactions / methyl 9-bromononanoate / methyl 8-formyloctanoate / methyl 11 or 17-methyloctadec-9-enoates
- Genard, S.,Patin, H.
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p. 397 - 406
(2007/10/02)
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- Models for bacteriorhodopsin-catalyzed dark cis-trans isomerization of bound retinal
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The syntheses of syn- and anti-2-aza-6-carboxymethylbicyclo[2.2.2]octane and syn and anti-2-aza-6-carboxypropyl[2.2.2]octane zwitterions are described. These compounds, which have secondary amines to form positively charged Schiff bases with retinal and a
- Seltzer, Stanley
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p. 4477 - 4483
(2007/10/02)
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- SYNTHESIS OF (Z)-4,5,13,14-TETRADEHYDRO-9(O)-METHANO-δ6(9&α)-PGI1
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A stereoselective synthesis of (Z)-4,5,13,14-tetradehydro-9(O)-methano-Δ6(9α)-PGI1, a potent prostacyclin analog, has been accomplished.
- Iseki, Katsuhiko,Shinoda, Masaki,Ishiyama, Chiyoko,Hayasi, Yosio,Yamada, Shun-ichi,Shibasaki, Masakatsu
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p. 559 - 562
(2007/10/02)
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- SYNTHESIS OF IRON(II) 'C2-CAPPED STRAPPED' PORPHYRIN COMPLEXES AND THEIR REACTION WITH DIOXYGEN
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The synthesis of potentially quinquedentate ligands based on a C2-capped porphyrinate ligand, the 'C2-capped strapped' ligands, is described where the 'strapping' groups contain a pyridine function.The iron(II) complexes of the ligands undergo reversible oxygenation at room temperature in toluene solution, and show good stability to autoxidation.Interestingly the products of decomposition are not μ-oxo dimers but are iron(III) species which can be directly reduced back to the active iron(II) form.The affinities of the complexes for dioxygen have been determined.The relatively low affinities of these new complexes are ascribed to inhibition of the motion of the iron(II), which must occur on the binding of O2.This is due to the locking of the complex in a 'domed' configuration, enhanced by the strapping group, and to unfavourable steric interactions of the strapping group with the parent porphyrin.
- Baldwin, Jack E.,Cameron, James H.,Crossley, Maxwell J.,Dagley, Ian J.
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p. 1739 - 1746
(2007/10/02)
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