- Regiodivergent synthesis of vinyl trifluoromethansulfonates γ/δ lactones: Via 1,6 addition/intramolecular one-pot annulation of 1,4-dihidropyridines derivated from pyridinyl propenones
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We report a novel intramolecular 1,6 oxa-Michael addition on substituted dihydropyridines to obtain 5 and 6 member ring lactones in an one-pot reaction starting from activated pyridinyl propenones, without organic catalysis or presence of bulky groups in
- álvarez-Toledano, Cecilio,Ballinas-Indili, Ricardo,Carmona-Reyes, Genaro,Sánchez-Vergara, María Elena,Toscano, R. Alfredo
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supporting information
(2021/12/29)
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- Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst
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3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).
- Liu, Yuan,Wang, Chen,Tong, Yixin,Ling, Yong,Zhou, Changjian,Xiong, Biao
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supporting information
p. 4422 - 4429
(2021/08/07)
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- COMPOUNDS AND METHODS FOR TREATING OR PREVENTING HEART FAILURE
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The present invention relates to the discovery of novel compounds that can be used to treat and/or prevent heart failure in a subject. In certain embodiments, the compounds of the invention are sulfide: quinone oxidoreductase (SQOR) inhibitors. In other e
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Page/Page column 104; 121
(2020/07/25)
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- Superelectrophilic nazarov cyclizations with N-heterocycles
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A series of Nazarov cyclizations has been studied involving N-heterocyclic-substituted 1-arylprop-2-en-1-one derivatives (aza-chalcones). Superacid catalyzed reactions of these derivatives provide good yields of heterocyclic-substituted 1-indanones. A mec
- Vuong, Hien,Amadou, Harouna,Stentzel, Michael R.,Klumpp, Douglas A.
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- Unsaturated ketone compound as well as preparation method and application thereof
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The present invention relates to a novel GPR52 antagonist. Specifically, the invention relates to an unsaturated ketone compound, a pharmaceutically acceptable salt, a stereoisomer or a prodrug molecule thereof, and a method for preparing a pharmaceutical composition thereof. The invention further relates to the use of the GPR52 antagonist as an orphan G protein coupled receptor GPR52 antagonist,and further relates to the use of the GPR52 antagonist in the preparation of drugs for preventing and treating Huntington's disease.
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Paragraph 0219-0222; 0256-0258
(2020/10/30)
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- Efficient catalytic performance of calcined tungstophosphoric acid for the Claisen-Schmidt condensation under solvent-free reaction
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Effect of calcination of tungstophosphoric acid catalyst was evaluated in terms of the synthesis of chalcone derivatives via Claisen-Schmidt condensation using the reaction of acetophenone and several substituted aldehydes. The catalyst was characterized before and after calcination by FT-IR to assess the effectiveness of the synthesis of the desired products. The calcined tungstophosphoric acid catalyst (HPW-CL) showed a better performance and high yield of Claisen-Schmidt products in a short period of time. It was also found out that the calcined tungstophosphoric acid provides a chemo selective, efficient and environmentally benign synthesis of chalcone in an excellent yield in a solvent-free system.
- Alharthi, Abdulrahman I.
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p. 2579 - 2584
(2019/10/02)
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- Green-to-Red Electrochromic Fe(II) Metallo-Supramolecular Polyelectrolytes Self-Assembled from Fluorescent 2,6-Bis(2-pyridyl)pyrimidine Bithiophene
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The structure and properties of metallo-supramolecular polyelectrolytes (MEPEs) self-assembled from rigid 2,6-bis(2-pyridyl)pyrimidine and the metal ions FeII and CoII are presented. While FeL1-MEPE (L1 = 1,4-bis[2,6-bis(2-pyridyl)pyrimidin-4-yl]benzene) is deep blue, FeL2- and CoL2-MEPE (L2 = 5,5′-bis[2,6-bis(2-pyridyl)pyrimidin-4-yl]-2,2′-bithiophene) are intense green and red in color, respectively. These novel MEPEs display a high extinction coefficient and solvatochromism. Ligand L2 shows a high absolute fluorescence quantum yield (Φf = 82%). Viscosity and static light-scattering measurements reveal that the molar masses of these MEPEs are in the range of 1 × 108 g/mol under the current experimental conditions. In water, FeL1-MEPE forms a viscous gel at 20 °C (c = 8 mM). Thin films of high optical quality are fabricated by dip coating on transparent conducting indium tin oxide (ITO) glass substrate. Optical, electrochemical, and electrochromic properties of the obtained MEPEs are presented. Green to red and blue to colorless electrochromism is observed for FeL2-MEPE and FeL1-MEPE, respectively. The results show that the electrochromic properties are affected by the ligand topology. The Fe-MEPEs show a reversible redox behavior of the FeII/FeIII couple at 0.86 and 0.82 V versus Fc+/Fc and display an excellent redox cycle stability under switching conditions. FeL2-MEPE in its oxidized state exhibits a broad absorption band covering the near-IR region (ca. 1500 nm) due to the ligand-to-metal charge transfer transition originating due to charge delocalization in the bithiophene spacer.
- Pai, Sandesh,Moos, Michael,Schreck, Maximilian H.,Lambert, Christoph,Kurth, Dirk G.
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p. 1418 - 1432
(2017/02/15)
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- Mechanistic insights into the role of PC- and PCP-type palladium catalysts in asymmetric hydrophosphination of activated alkenes incorporating potential coordinating heteroatoms
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The impact of the structural attributes of chiral PC- and PCP-palladium catalysts was investigated in the asymmetric hydrophosphination of various heterocycle-functionalized enone substrates. Due to the architecture of the catalysts, they are confronted w
- Yang, Xiang-Yuan,Jia, Yu-Xiang,Tay, Wee Shan,Li, Yongxin,Pullarkat, Sumod A.,Leung, Pak-Hing
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supporting information
p. 13449 - 13455
(2016/09/04)
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- Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach
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Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.
- Ventura, Thatiana Lopes Biá,Calixto, Sanderson Dias,De Azevedo Abrahim-Vieira, Bárbara,De Souza, Alessandra Mendon?a Teles,Mello, Marcos Vinícius Palmeira,Rodrigues, Carlos Rangel,De Mariz E Miranda, Leandro Soter,De Souza, Rodrigo Octavio Mendon?a Alves,Leal, Ivana Correa Ramos,Lasunskaia, Elena B.,Muzitano, Michelle Fraz?o
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p. 8072 - 8093
(2015/05/20)
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- Regioselective synthesis of triazoles via base-promoted oxidative cycloaddition of chalcones with azides in aqueous solution
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A base-promoted oxidative cycloaddition of chalcones with azides in aqueous solution has been developed under transition-metal-free conditions, which provides a green method for the regioselective synthesis of trisubstituted triazoles in good yields.
- Yang, Wenchao,Miao, Tao,Li, Pinhua,Wang, Lei
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p. 95833 - 95839
(2015/11/24)
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- Quantum Chemical Study on the Corrosion Inhibition Property of Some Heterocyclic Azole Derivatives
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Quantum chemical calculations based on density functional theory (DFT) method were performed on heterocyclic azole derivatives as corrosion inhibitors for mild steel in acid media to investigate the relationship between molecular structure of the inhibito
- Anusuya,Sounthari,Saranya,Parameswari,Chitra
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p. 1741 - 1750
(2016/01/25)
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- Synthesis and antimycobacterial activity of some N1-[1-[3-aryl-1- (pyridin-2-, 3-, or 4-yl)-3-oxo]propyl]-2-pyridinecarboxamidrazones
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N1-[1-[3-aryl-1-(pyridin-2-,3-, and 4-yl)-3-oxo]propyl]-2- pyridinecarboxamidrazone derivatives were synthesized and tested for their in vitro antimycobacterial activity. Some compounds showed interesting activity against a strain of Mycobacter
- Mamolo, Maria Grazia,Falagiani, Valeria,Vio, Luciano,Banfi, Elena
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p. 761 - 767
(2007/10/03)
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- 2-Substituted 1-Azabicycloalkanes, a New Class of Non-Opiate Antinociceptive Agents
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2-Substituted 1-azabicycloalkanes (3- and 5-aryloctahydroindolizines 2 and 11, 3-cyclohexyloctahydroindolizine 12, 4-aryloctahydroquinolizines 13, and 3-arylhexahydropyrrolizines 14) constitute a new class of non-opiate antinociceptive agents.These compou
- Carson, John R.,Carmosin, Richard J.,Vaught, Jeffry L.,Gardocki, Joseph F.,Costanzo, Michael J.,et al.
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p. 2855 - 2863
(2007/10/02)
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- Synthesis of 3-Cyano-2-methylpyridines Substituted with Heteroaromatics
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A series of title compounds were easily prepared by the sonication of α,β-unsaturated carbonyl compound in acetonitril in the presence of potassium t-butoxide.
- Shibata, Katsuyoshi,Katsuyama, Isamu,Matsui, Masaki,Muramatsu, Hiroshiga
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p. 161 - 165
(2007/10/02)
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- Heterocycles. 3. Synthesis and Spectral Data of Some 2-Pyrazolines
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The reaction of 1,3-diaryl-2-propen-1-ones (Ia-o) with hydrazine and methyl- and phenylhydrazine produced different substituted 2-pyrazolines (III).The structures of these products were evident from their chemical and spectroscopic analysis.
- El-Rayyes, Nizar R.,Hovakeemian, George H.,Hmoud, Hayat S.
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p. 225 - 229
(2007/10/02)
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- ALDOL CONDENSATIONS WITH METAL(II) COMPLEX CATALYSTS.
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Aldol condensations of aldehydes with ketones catalyzed by the first-row transition metal(II) complexes have been widely studied. Complexes of Co(II), Ni(II), Cu(II), and Zn(II) acetates with 2,2 prime -bypyridine were effective catalysts to afford cross-aldol condensation products, alpha , beta ,-unsaturated ketones, in high yields without any self-condensation products. The reaction of 2-butanone, unsymmetrical aliphatic ketone, with benzaldehyde took place regioselectively to give base-catalyzed-type products.
- Irie,Watanabe
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p. 1366 - 1371
(2007/10/02)
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