- Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation
-
ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.
- Kim, Hun Young,Oh, Kyungsoo,Si, Tengda
-
p. 9216 - 9221
(2019/10/08)
-
- A diversity-oriented synthesis of polyheterocycles: Via the cyclocondensation of azomethine imine
-
Pd-Catalyzed sequential reactions to afford skeletally diverse molecules are described. The reaction involved azomethine imine formation and a cyclocondensation reaction as individual steps. The methodology provides excellent regio- and stereocontrol. Skeletal diversity was ensured by changing the electrophilic counterpart of azomethine imine. Due to its broader diversity and complexity, the DOS methodology is likely to benefit drug discovery and development in the future.
- Ansari, Arshad J.,Pathare, Ramdas S.,Kumawat, Anita,Maurya, Antim K.,Verma, Sarika,Agnihotri, Vijai K.,Joshi, Rahul,Metre, Ramesh K.,Sharon, Ashoke,Pardasani,Sawant, Devesh M.
-
supporting information
p. 13721 - 13724
(2019/09/16)
-
- Discovery of a PCAF Bromodomain Chemical Probe
-
The p300/CBP-associated factor (PCAF) and related GCN5 bromodomain-containing lysine acetyl transferases are members of subfamily I of the bromodomain phylogenetic tree. Iterative cycles of rational inhibitor design and biophysical characterization led to the discovery of the triazolopthalazine-based L-45 (dubbed L-Moses) as the first potent, selective, and cell-active PCAF bromodomain (Brd) inhibitor. Synthesis from readily available (1R,2S)-(?)-norephedrine furnished L-45 in enantiopure form. L-45 was shown to disrupt PCAF-Brd histone H3.3 interaction in cells using a nanoBRET assay, and a co-crystal structure of L-45 with the homologous Brd PfGCN5 from Plasmodium falciparum rationalizes the high selectivity for PCAF and GCN5 bromodomains. Compound L-45 shows no observable cytotoxicity in peripheral blood mononuclear cells (PBMC), good cell-permeability, and metabolic stability in human and mouse liver microsomes, supporting its potential for in vivo use.
- Moustakim, Moses,Clark, Peter G. K.,Trulli, Laura,Fuentes de Arriba, Angel L.,Ehebauer, Matthias T.,Chaikuad, Apirat,Murphy, Emma J.,Mendez-Johnson, Jacqui,Daniels, Danette,Hou, Chun-Feng D.,Lin, Yu-Hui,Walker, John R.,Hui, Raymond,Yang, Hongbing,Dorrell, Lucy,Rogers, Catherine M.,Monteiro, Octovia P.,Fedorov, Oleg,Huber, Kilian V. M.,Knapp, Stefan,Heer, Jag,Dixon, Darren J.,Brennan, Paul E.
-
supporting information
p. 827 - 831
(2017/01/14)
-
- METHODS AND COMPOSITIONS FOR SELECTIVE AND TARGETED CANCER THERAPY
-
Provided herein are methods and compositions for selective and targeted cancer therapy, in particular certain benzothiophenes, benzothiazoles, oxalamides, N-acyl ureas and chromones, and their use in selectively treating certain adenocarcinomas. In some embodiments, the selective toxicity of the compounds may be mediated through SCD1 and/or CYP450 such as CYP4F11.
- -
-
Page/Page column 228
(2015/03/28)
-
- Novel dihydroquinolizinones for the treatment and prophylaxis of hepatitis B virus infection
-
The invention provides novel compounds having the general formula: wherein R1, R2, R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds.
- -
-
Paragraph 1180; 1181
(2015/08/04)
-
- NOVEL DIHYDROQUINOLIZINONES FOR THE TREATMENT AND PROPHYLAXIS OF HEPATITIS B VIRUS INFECTION
-
The invention provides novel compounds having the general formula (I) wherein R1, R2 R3, R4, R5 and R6 are as described herein, compositions including the compounds and methods of using the compounds in the treatment of the hepatitis B virus.
- -
-
Page/Page column 148; 149
(2015/09/23)
-
- Iron-catalyzed tandem one-pot addition and cyclization of the blaise reaction intermediate and nitroolefins: Synthesis of substituted NH-pyrroles from nitriles
-
The iron-catalyzed addition and cyclization of the Blaise reaction intermediate and nitroolefins to synthesize highly functionalized NH-pyrroles in a tandem one-pot manner from nitriles has been developed. This reaction shows good functional group tolerance and affords a broad spectrum of substituted NH-pyrroles in good yields. Copyright
- Zhao, Mi-Na,Liang, Hao,Ren, Zhi-Hui,Guan, Zheng-Hui
-
supporting information
p. 221 - 226
(2013/03/13)
-
- Highly enantioselective reduction of α-methylated nitroalkenes
-
Highly selective: The reduction of α-methyl-substituted nitroalkenes succeeds in a highly enantioselective fashion with an ene reductase from Gluconobacter oxydans. Under optimized reaction conditions the desired nitroalkanes are formed with enantiomeric excesses of up to 95% in these biotransformations. Copyright
- Burda, Edyta,Re?, Tina,Winkler, Till,Giese, Carolin,Kostrov, Xenia,Huber, Tobias,Hummel, Werner,Gr?ger, Harald
-
supporting information
p. 9323 - 9326
(2013/09/12)
-
- Straightforward synthesis of nitroolefins by microwave- or ultrasound-assisted Henry reaction
-
β-Nitroalcohol or nitroethylene derivatives can be obtained from aryl aldehydes and nitromethane under Henry condensation conditions. We present a new modification using microwave irradiation or ultrasound as the energy source. Microwave irradiation allowed a novel one-pot synthesis of nitroolefins from aryl aldehydes using ammonium acetate as a catalyst without solvent. Different reaction conditions, such as base, solvent, and reaction time were studied. Only small amounts of β-hydroxyl nitro compounds were isolated, using microwave irradiation for less than 25 min. In contrast, the use of ultrasound increased the yield of the nitroalcohols.
- Rodríguez, Jose M.,Dolors Pujol
-
experimental part
p. 2629 - 2632
(2011/06/10)
-
- Enzymatic enantiomeric resolution of phenylethylamines structurally related to amphetamine
-
Both enantiomers of several phenylethylamines, structurally related to amphetamine, have been prepared in good yields and excellent enantiomeric purity by enzymatic kinetic resolution using CAL-B and ethyl methoxyacetate as the acyl donor. In the case of the 4-hydroxyderivative of amphetamine (compound 4i), the S enantiomer racemized possibly in a dynamic kinetic resolution (DKR) under the enzymatic conditions used. The Royal Society of Chemistry 2011.
- Munoz, Lourdes,Rodriguez, Anna M.,Rosell, Gloria,Bosch, M. Pilar,Guerrero, Angel
-
experimental part
p. 8171 - 8177
(2012/01/04)
-
- Ambiphilic dual activation role of a task-specific ionic liquid: 2-hydroxyethylammonium formate as a recyclable promoter and medium for the green synthesis of β-nitrostyrenes
-
A cost-effective task-specific ionic liquid, 2-hydroxyethylammonium formate, efficiently promotes the condensation of nitroalkanes with various aldehydes to produce β-nitrostyrenes in high to excellent yields at room temperature. This reaction does not involve any hazardous organic solvent and toxic catalyst. The ionic liquid is recovered and recycled for subsequent reactions. In addition, a novel mechanism has been proposed invoking ambiphilic dual activation influence of the ionic liquid.
- Alizadeh, Abdolhamid,Khodaei, Mohammad M.,Eshghi, Ali
-
scheme or table
p. 8295 - 8298
(2011/03/17)
-
- 2-Benzyl-2-methyl-2H-benzimidazole 1,3-dioxide derivatives: Spectroscopic and theoretical study
-
The spectroscopic behavior of 2-benzyl-2-methyl-2H-benzimidazole 1,3-dioxide derivatives in solution was studied in terms of electronic and nuclear magnetic resonance (1H and 13C NMR) techniques. The experimental spectra were compared to the theoretical ones, obtained at DFT level, proving that the compounds adopt in solution a bird-like conformational distribution. Also, theoretically this conformational distribution resulted the most stable in gas phase. Infrared spectroscopy was used to study solid state behavior identifying experimentally the N-O stretching near to 1380, 1365 and 1225 cm-1 and the vibrational benzimidazole skeleton near to 1610 and 1590 cm-1. The vibrational spectrum was satisfactorily described by DFT calculations funding the N-O stretching as a coupled vibration near to 1470, 1350 and 1285 cm-1. The fragmentation that takes place in mass spectrometry was assigned for all of the new derivatives.
- Merlino, Alicia,Boiani, Mariana,Cerecetto, Hugo,Gonzalez, Mercedes
-
p. 540 - 549
(2008/02/07)
-
- MAO inhibition by arylisopropylamines: The effect of oxygen substituents at the β-position
-
Twenty-nine arylisopropylamines, substituted at the β-position of their side chain by an oxo, hydroxy, or methoxy group, were evaluated in vitro as MAO-A and MAO-B inhibitors. The oxo derivatives ('cathinones') were in general less active as MAO-A inhibitors than the corresponding arylisopropylamines, but exhibited an interesting MAO-B inhibiting activity, which was absent in the hydroxy, methoxy, and β-unsubstituted analogues. These results suggest that selective affinity for the two MAO isoforms in this family of compounds is modulated not only by the aryl substitution pattern but also by the side-chain substituents on the arylalkylamine scaffold.
- Osorio-Olivares, Mauricio,Rezende, Marcos Caroli,Sepulveda-Boza, Silvia,Cassels, Bruce K.,Fierro, Angelica
-
p. 4055 - 4066
(2007/10/03)
-
- Microwave-induced solvent-free, rapid and efficient synthesis of conjugated nitroalkenes using sulfated zirconia
-
Sulfated Zirconia catalyzed synthesis of conjugated nitroalkenes has been carrried out under solvent-free condition using sulfated zirconia. Recyclability of catalyst, isolation of pure products by simple filtration and evaporation are important features of this method.
- Bandgar,Kasture
-
p. 1239 - 1241
(2007/10/03)
-
- Minute synthesis of electrophilic alkenes under microwave irradiation
-
Condensation of carbonyl derivatives 2 with active methylene compounds 1 is efficiently achieved, within 3 to 15 minutes under microwave irradiation by a solvent free reaction in the presence of carefully adjusted amounts of piperidine leading to Knocvenagel products 3 in good to excellent yields.
- Ayoubi,Texier-Boullet,Hamelin
-
p. 258 - 260
(2007/10/02)
-
- Inter- and Intramolecular Cycloadditions of Nitroalkenes with Olefins. 2-Nitrostyrenes
-
Aromatic nitroalkenes 9 - 12 underwent Lewis acid catalyzed cycloadditions with various cyclic alkenes to afford high yields of nitronates 25 - 30 with exclusive anti selectivity.Hammett studies helped to further delineate the role of the Lewis acid.Reaction of nitroalkenes 8 and 10 with various cyclic dienes in the presence of a Lewis acid demonstrated the ability of nitroalkenes to behave as dienes in cycloadditions.The major products were the syn diastereomers which arise from an endo-folded transition structure.Finally, intramolecular cycloaddition of 36 - 39 allowed a correlation between the stereochemical course of the reaction and positions of sp2 centers in the tether to be addressed.
- Denmark, Scott E.,Kesler, Brenda S.,Moon, Young-Choon
-
p. 4912 - 4924
(2007/10/02)
-
- Kinetics of reaction of para-substituted β-nitrostyrenes and β-methyl-β-nitrostyrenes with n-butylamine
-
The kinetics of addition of n-butylamine to β-nitrostyrene and β-methyl-β-nitrostyrene and their para-substituted derivatives in acetonitrile at four different temperatures have been followed spectrophotometrically.The order in is unity and in (n-butylamine) it is non-integral.On the basis of the observed kinetic data, a stepwise mechanism involving the formation of zwitterionic addition complex in an equilibrium step followed by conversion into the reaction product via proton transfer in catalytic route by the amine has been proposed.The study of effect of substituents in these reactions shows that the electron-withdrawing substituents accelerate the reaction and electronreleasing substituents retard it.Good Hammett correlations have been observed in both the reaction series.
- Shunmugasundaram, A,Thanulingam, T Lekshmana,Murugesan, R
-
p. 609 - 613
(2007/10/02)
-
- Cathodic Reduction of 1-Nitroalkenes to Oximes and Primary Amines
-
1-Nitroalkenes are reduced in high yields at -0.3 to -0.5 V (vs.SCE) at a mercury or graphite cathode to oximes.At higher cathodic reduction potentials (-1.1 V) primary amines are selectively obtained in fair yields.Nitroalkadienes are selectively reduced at the double bond conjugated with the nitro group to either the oxime or amine.Key Words: Electrochemistry / 1-Nitroalkenes, reduction of / Oximes / Amines
- Wessling, Michael,Schaefer, Hans J.
-
p. 2303 - 2306
(2007/10/02)
-
- Porphyrin synthesis from nitrocompounds
-
A new porphyrin synthesis starting from nitroalkenes or their equivalents is described. For example, octaethylporphyrin, coproporphyrin, porphyrin-1,2,3,4,5,6,7,8 octapropionic acid, and 2,7,12,17 tetraarylporphyrin are prepared in good yield from readily available materials such as 1-nitropropane, nitroethane, nitromethane, and aldehydes.
- Ono, Noboru,Kawamura, Hisayuki,Bougauchi, Masahiro,Maruyama, Kazuhiro
-
p. 7483 - 7496
(2007/10/02)
-
- REDUCTION OF ARYLALKYLAZOMETHINES WITH SODIUM BOROHYDRIDE
-
The secondary amines R1R2C6H3CH2CH(CH3)NHCHR5CHR6(CH2)nC6H3R3R4 were synthesized by the reduction of the respective azomethines with sodium borohydride.The reaction was conducted in anhydrous methanol in the presence of hydrogen chloride with the azomethine and hydrogen chloride in a molar ratio of 1:1.The yield was 50-90percent.The erythro and threo isomers were isolated, and the data from the IR spectra of the isomers are given.
- Dumpis, M. A.,Kudryashova, N. I.,Veresova, M. A.
-
p. 1332 - 1337
(2007/10/02)
-