- Synthesis of trifluoromethylaryl diazirine and benzophenone derivatives of etomidate that are potent general anesthetics and effective photolabels for probing sites on ligand-gated ion channels
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To locate the binding sites of general anesthetics on ligand-gated ion channels, two derivatives of the intravenous general anesthetic etomidate (2-ethyl 1-(phenylethyl)-1H-imidazole-5-carboxylate), in which the 2-ethyl group has been replaced by photoact
- Husain, S. Shaukat,Nirthanan, Selvanayagam,Ruesch, Dirk,Solt, Ken,Cheng, Qi,Li, Guo-Dong,Arevalo, Enrique,Olsen, Richard W.,Raines, Douglas E.,Forman, Stuart A.,Cohen, Jonathan B.,Miller, Keith W.
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Read Online
- Imidazopyridine-fused [1,3]diazepinones: modulations of positions 2 to 4 and their impacts on the anti-melanoma activity
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A series of 19 novel pyrido-imidazodiazepinones, with modulations of positions 2, 3 and 4 of the diazepine ring were synthesised and screened for their in vitro cytotoxic activities against two melanoma cell lines (A375 and MDA-MB-435) and for their poten
- Ali, Lamiaa M. A.,Baccon-Sollier, Paul Le,Cuq, Pierre,Lichon, Laure,Malki, Yohan,Masurier, Nicolas,Maye, Morgane,Vincent, Laure-Ana?s
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p. 935 - 949
(2020/04/17)
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- Chemoselective reduction of aldehydes: Via a combination of NaBH4 and acetylacetone
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A bench-stable combination of NaBH4-acetylacetone was developed for the efficient chemoselective reduction of aldehydes in the presence of ketones. This method offers a useful synthetic protocol for distinguishing carbonyl reaction sites, and its synthetic utility is reflected by its moisture tolerance and high efficiency in a variety of complex settings.
- Sui, Guoqing,Lv, Qingyun,Song, Xiaoqing,Guo, Huihui,Dai, Jiatong,Ren, Li,Lee, Chi-Sing,Zhou, Wenming,Hao, Hong-Dong
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p. 15793 - 15796
(2019/10/19)
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- An unusual chemoselective oxidation strategy by an unprecedented exploration of an electrophilic center of DMSO: A new facet to classical DMSO oxidation
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A conceptually new dimethyl sulfoxide (DMSO) based oxidation process without the use of any activator has been demonstrated for the oxidation of active methylenes and benzhydrols. The developed protocol utilizes the electrophilic center of DMSO for oxidation, which was unexplored before. Mechanistic investigation has confirmed that the source of oxygen is DMSO.
- Chebolu, Rajesh,Bahuguna, Ashish,Sharma, Reena,Mishra, Vivek Kumar,Ravikumar
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supporting information
p. 15438 - 15441
(2015/10/20)
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- Transition-metal-free, ambient-pressure carbonylative cross-coupling reactions of aryl halides with potassium aryltrifluoroborates
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We disclose an unprecedented transition-metal-free carbonylative cross coupling of aryl halides with potassium aryl trifluoroborates even at atmospheric pressure of carbon monoxide. This protocol is efficient, operationally simple, and shows wide scope with regard to both aryl halides and potassium aryl trifluoroborates containing a series of active functional groups.
- Jin, Fengli,Han, Wei
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supporting information
p. 9133 - 9136
(2015/06/08)
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- Palladium-catalyzed hydroxymethylation of aryl-and heteroarylboronic acids using aqueous formaldehyde
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Cyclometallated NHC palladium complexes prepared from palladium(II) acetate [Pd(OAc)2] and unsymmetrical 1,3-diarylimidazolinium salts catalyzed the hydroxymethylation of (hetero)arylboronic acids using an excess amount of formalin to afford (hetero)arylm
- Yamamoto, Tetsuya,Zhumagazin, Azamat,Furusawa, Takuma,Tanaka, Ryoji,Yamakawa, Tetsu,Oe, Yohei,Ohtab, Tetsuo
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supporting information
p. 3525 - 3529
(2015/01/09)
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- Palladium-catalyzed arylation of aldehydes with bromo-substituted 1,3-diaryl-imidazoline carbene ligand
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The combination of 0 valent palladium precursor and bromo-substituted 1,3-diaryl-imidazoline carbene ligand precursor such as 1-(2-bromophenyl)-3-(2,6-diisopropylphenyl)-imidazolinium chloride 1a exhibited high catalytic activity for the 1,2-addition of arylboronic acids to aldehydes including aqueous formaldehyde.
- Yamamoto, Tetsuya,Furusawa, Takuma,Zhumagazin, Azamat,Yamakawa, Tetsu,Oe, Yohei,Ohta, Tetsuo
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- CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS
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Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.
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- Selective aldehyde reduction in ketoaldehydes with NaBH4-Na 2CO3-H2O at room temperatures
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A variety of aliphatic and aromatic ketoaldehydes were reduced to the corresponding ketoalcohols with a mixture of sodium borohydride (1.2 equivalents) and sodium carbonate (sixfold molar excess) in water. Reactions were performed at room temperatures(typically) 2 h, and yields of isolated products generally ranged from 70% to 85%. A bis-carbonate-borane complex, [(BH3)2CO2]2- 2Na+, possibly formed from the reagent mixture, is likely the active reductant. The moderated reactivity of this acylborane species would explain the chemoselectivity observed in the reactions. The readily available reagents and the mild aqueous conditions make for ease of operation and environmental compatibility, and make a useful addition to available methodology. Copyright
- Chandrasekhar, Sosale,Shrinidhi, Annadka
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p. 2051 - 2056
(2014/07/07)
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- Palladium-catalyzed direct hydroxymethylation of aryl halides and triflates with potassium acetoxymethyltrifluoroborate
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Suzuki-Miyaura cross-coupling reactions of aryl halides and triflates with potassium acetoxymethyltrifluoroborate afforded the corresponding aryl and heteroaryl methanol products in moderate to excellent yields.
- Murai, Norio,Yonaga, Masahiro,Tanaka, Keigo
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supporting information; experimental part
p. 1278 - 1281
(2012/04/23)
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- TAILORED CONTROL OF SURFACE PROPERTIES BY CHEMICAL MODIFICATION
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A process for producing a substrate having an adhesive surface, which process comprises: (a) contacting the substrate with a carbene precursor, which carbene precursor is a compound of the following formula (1): whose substituent groups are SP defined herein, provided that when R is aryl or heteroaryl, said aryl or heteroaryl may be substituted by one, two, three, four or five groups, which groups are independently selected from various groups including -LB-WB; and (b) either: (i) when WA or WB comprises an adhesive functional group, generating a carbene reactive intermediate from the carbene precursor so that it reacts with the substrate to functionalise the surface, thereby yielding said substrate having an adhesive surface; or (ii) when WA or WB comprises a group which is a precursor of an adhesive functional group, generating a carbene reactive intermediate from the carbene precursor so that it reacts with the substrate to functionalise the surface, and (c) converting said group which is a precursor into an adhesive functional group thereby yielding said substrate having an adhesive surface. The invention further relates to carbene precursor compounds for use in the process, substrates produced by the process and to processes for preparing certain precursor compounds.
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Page/Page column 26-27
(2010/04/23)
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- Efficient routes toward 4-[(2-aminoethoxy)methyl]benzophenone
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The novel benzophenone derivative 4-[(2-aminoethoxy)methyl]benzophenone (4) was synthesized via two pathways, commencing from 4-(bromomethyl)-benzophenone (1) and methyl 4-(bromomethyl)benzoate (7) respectively. All new compounds were characterized by su
- Tang, Rui-Ren,Zhu, Jin-Juan,Luo, Yi-Ming
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p. 421 - 427
(2007/10/03)
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- Formal intramolecular photoredox chemistry of meta-substituted benzophenones
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(Chemical Equation Presented) Photolysis of 3-(hydroxymethyl)benzophenone (1) in aqueous solution (pH -4 M) conditions. Evidence suggests that the highly efficient (Φ ~ 0.6) reaction involves a unimolecular mechanism and an overall formal intramolecular photoredox process, which requires electronic communication between the 1,3-positions of the benzene ring, an unprecedented example of the photochemical meta effect. The photoredox reaction was not observed in organic solvents, where only photoreduction of the benzophenone moiety was observed.
- Mitchell, Devin,Lukeman, Matthew,Lehnherr, Dan,Wan, Peter
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p. 3387 - 3389
(2007/10/03)
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- Oxidation of alcohols with nitroxyl radical under polymer-supported two-phase conditions
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The oxidation of alcohols to carbonyl compounds was studied using potassium hexacyanoferrate(III) mediated by nitroxyl radical as the catalyst under polymer-supported organic-aqueous two-phase conditions. Primary alcohols are readily oxidized to the corresponding aldehydes in excellent yield with no over-oxidation to carboxylic acids. Secondary alcohols are converted to the corresponding ketones with a much lower efficiency. The oxidation reactions of primary alcohols in the presence of secondary alcohols is strongly favored. Primary-secondary diols are selectively transformed into hydroxy aldehydes with small amounts of ketoaldehydes, the amount of isomeric keto alcohols remaining is less than 1%.
- Yoshitomo, Kashiwagi,Chiba, Shinya,Anzai, Jun-ichi
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p. 1545 - 1549
(2007/10/03)
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- Synthesis and photochemistry of two cleavable heterobifunctional benzophenone protein crosslinkers
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Two new heterobifunctional protein crosslinkers were synthesized. These reagents contain the cysteine reactive maleimido group connected via a cleavable ester linkage to the benzophenone photoactivatable group.
- Oatis Jr., John E.,Knapp, Daniel R.
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p. 1665 - 1668
(2007/10/03)
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- Efficient and highly selective oxidation of Primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts
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2,2,6,6-Tetramethyl-1-piperidinyloxy catalyzes efficient oxidation of primary alcohols to aldehydes by N-chlorosuccinimide, in a biphasic dichloromethane - aqueous pH 8.6 buffer system in the presence of tetrabutylammonium chloride. Aliphatic, benzylic, and allylic alcohols are readily oxidized with no overoxidation to carboxylic acids. Secondary alcohols are oxidized to ketones with a much lower efficiency. Very high chemoselectivities are observed when primary alcohols are oxidized in the presence of secondary ones. Primary - secondary diols are selectively transformed into hydroxy aldehydes, with, in some cases, no detectable formation of the isomeric keto alcohols.
- Einhorn, Jacques,Einhorn, Cathy,Ratajczak, Fabien,Pierre, Jean-Louis
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p. 7452 - 7454
(2007/10/03)
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- Multiple-photon chemistry in the benzophenone photoreduction during laser-jet photolysis: Effect of alcohol solvent on cross-coupling versus hydrogen abstraction of the electronically excited hydroxydiphenylmethyl radical
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The ground state of the hydroxydiphenylmethyl radical (1) leads to benzpinacol (2) through head-to-head coupling and the diols 3 as cross-coupling product. In contrast, under the high-intensity conditions of the laser-jet photolysis, the excited radical 1* couples in the para position to afford the benzophenone derivatives 4 (head-to-tail coupling) (higher spin density at the para position/AM1 calculations). The major two-photon product is benzhydrol (5). The pronounced increase in hydrogen atom abstraction from MeOH to iPrOH by 1* is explained in terms of the greater electrophilic character of the electronically excited radical 1* versus its ground state.
- Adam, Waldemar,Walther, Barbara
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p. 10399 - 10404
(2007/10/03)
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- Lanthanoids in Organic Synthesis. I. The Novel Reduction of Carboxylic Acids with Samarium Diiodide-Base System
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Aromatic and aliphatic carboxylic acids were rapidly reduced with samarium diiodide by the addition of base in the presence of protic solvent at room temperature to the corresponding alcohols.Sodium benzoate was similarly reduced with samarium diiodide in the presence of H2O in a good yield.In the similar reactions of benzoic acid derivatives bearing carboxyl, formyl, carbamoyl, methoxyl, and chloro groups, these functional groups were also reduced to the corresponding alcohol or amine derivatives.Interestingly, the carboxyl and formyl groups of benzoic acids were partly reduced into the methyl group.
- Kamochi, Yasuko,Kudo, Tadahiro
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p. 3049 - 3054
(2007/10/02)
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- A Simple Economical Procedure for Selective Reduction of Aldehydes in Presence of Ketones
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A simple, efficient, and economical method for chemoselective reduction of aldehydes in the presence of ketones using stoichiometric amounts of sodium borohydride under phase-transfer catalysis is described.Aliphatic, aromatic and unsaturated aldehydes are reduced rapidly in high yields while dialkyl, aralkyl, diaryl and cycloaliphatic ketones are practically inert under the same conditions.Some exceptions are noted.The scope of the present method is illustrated with suitable examples of selective and competitive reductions.The high reactivity of the phase-transferred borohydride species as compared to that of pre-formed quaternary ammonium borohydrides is noted.
- Rao, C. Someswara,Deshmukh, A. A.,Patel, B. J.
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p. 626 - 629
(2007/10/02)
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- CHEMOSELECTIVE REDUCTION OF ALDEHYDES WITH TETRA-n-BUTYLAMMONIUM TRIACETOXYBOROHYDRIDE
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Aldehydes, but not ketones, are smoothly reduced to alcohols by tetra-n-butylammonium triacetoxyborohydride in refluxing benzene.
- Nutaitis, Charles F.,Gribble, Gordon W.
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p. 4287 - 4290
(2007/10/02)
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- NEW OBSERVATIONS ON THE PHOTOPINACOLIZATION OF BENZOPHENONE IN ALIPHATIC ALCOHOLS
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Irradiation of benzophenone in alcohol solutions produces unsymmetrical pinacols and para-coupled products as well as benzpinacol; the product composition depends on light intensity.
- Rubin, Mordecai B.
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p. 4615 - 4618
(2007/10/02)
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