- Supramolecular organization of bis(3-halo-4-dimethylaminobenzylidene) hydrazines
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Bis(3-bromo-4-dimethylaminobenzylidene)hydrazine and bis(3-chloro-4- dimethylaminobenzylidene)hydrazine have been synthesized, and their monoclinic crystal structures solved in space group P21/c. For the bromo derivative at 150 K, a = 10.4505(2
- Guieu, Samuel,Rocha, Jo?o,Silva, Artur M.S.
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Read Online
- Toward bioluminescence in the near-infrared region: Tuning the emission wavelength of firefly luciferin analogues by allyl substitution
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The synthesis and bioluminescence of allyl-substituted luciferin derivatives as substrates for firefly luciferase are reported. The allylation of luciferins induced bathochromic shift (15–40 nm) of the bioluminescence emission. Upon combination with other chemical modifications for bioluminescence wavelength tuning, novel red emitting luciferin analogues were obtained with emission maxima at 685 and 690 nm.
- Kitada, Nobuo,Saitoh, Tsuyoshi,Ikeda, Yuma,Iwano, Satoshi,Obata, Rika,Niwa, Haruki,Hirano, Takashi,Miyawaki, Atsushi,Suzuki, Koji,Nishiyama, Shigeru,Maki, Shojiro A.
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Read Online
- Ni-NiO heterojunctions: a versatile nanocatalyst for regioselective halogenation and oxidative esterification of aromatics
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Herein, we report a facile method for the synthesis of Ni-NiO heterojunction nanoparticles, which we utilized for the nuclear halogenation reaction of phenol and substituted phenols usingN-bromosuccinimide (NBS). A remarkablepara-selectivity was achieved for the halogenated products under semi-aqueous conditions. Interestingly, blocking of thepara-position of phenol offeredortho-selective halogenation. In addition, the Ni-NiO nanoparticles catalyzed the oxidative esterification of carbonyl compounds with alcohol, diol or dithiol in the presence of a catalytic amount of NBS. It was observed that the aromatic carbonyls substituted with an electron-donating group favoured nuclear halogenation, whereas an electron-withdrawing group substitution in carbonyl compounds facilitated the oxidation reaction. In addition, the catalyst was magnetically separated and recycled 10 times. The tuned electronic structure at the Ni-NiO heterojunction controlled selectivity and activity as no suchpara-selectivity was observed with commercially available NiO or Ni nanoparticles.
- Bhardwaj, Nivedita,Goel, Bharat,Indra, Arindam,Jain, Shreyans K.,Singh, Ajit Kumar,Tripathi, Nancy
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p. 14177 - 14183
(2021/08/16)
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- Design and optimisation of a small-molecule TLR2/4 antagonist for anti-tumour therapy
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In anti-tumour therapy, the toll-like receptor 2/4 (TLR2/4) signalling pathway has been a double-edged sword. TLR2/4 agonists are commonly considered adjuvants for immune stimulation, whereas TLR2/4 antagonists demonstrate more feasibility for anti-tumour therapy under specific chronic inflammatory situations. In individuals with cancer retaliatory proliferation and metastasis after surgery, blocking the TLR2/4 signalling pathway may produce favourable prognosis for patients. Therefore, here, we developed a small-molecule co-inhibitor that targets the TLR2/4 signalling pathway. After high-throughput screening of a compound library containing 14 400 small molecules, followed by hit-to-lead structural optimisation, we finally obtained the compound TX-33, which has effective inhibitory properties against the TLR2/4 signalling pathways. This compound was found to significantly inhibit multiple pro-inflammatory cytokines released by RAW264.7 cells. This was followed by TX-33 demonstrating promising efficacy in subsequent anti-tumour experiments. The current results provide a novel understanding of the role of TLR2/4 in cancer and a novel strategy for anti-tumour therapy.
- Chen, Hekai,Kong, Jun,Li, Tian,Xu, Qun,Yin, Hang,Zhang, Liwei
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supporting information
p. 1771 - 1779
(2021/11/19)
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- Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent
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A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.
- Arrieta, Ana,Cossío, Fernando P.,Granados, Albert,Shafir, Alexandr,Vallribera, Adelina
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p. 2142 - 2150
(2020/03/11)
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- Alkylammoniotrifluoroborate functionalized polystyrenes: Polymeric pre-catalysts for the metal-free borylation of heteroarenes
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Three polymeric versions of ansa-N,N-dialkylammoniumtrifluoroborate ambiphilic molecules based on the styrene motif (poly(1-NMe2H+-2-BF3--4-styrene) (P-Me), poly(1-NEt2H+-2-BF3--4-styrene) (P-Et) and poly(1-piperidinyl-H+-2-BF3--4-styrene) (P-Pip)) were synthesized, characterized and tested as heterogeneous pre-catalysts for the borylation of electron-rich heteroarenes. These heterogeneous versions of previously reported pre-catalysts show similar reactivity patterns and represent the first examples of solid-supported FLP metal-free catalysts for the C-H borylation of heteroarenes.
- Bouchard, Nicolas,Fontaine, Frédéric-Georges
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supporting information
p. 4846 - 4856
(2019/04/17)
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- Environmentally benign indole-catalyzed position-selective halogenation of thioarenes and other aromatics
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Halogenated aromatic compounds are the cores of many pharmaceutical, agricultural and chemical products but they are commonly prepared using electrophilic halogenation reactions in non-green chlorinated solvents under harsh conditions. A separate problem happens in the aromatic halogenation of thioarenes because they readily undergo oxidative side-reactions. Herein we report an environmentally benign electrophilic bromination of aromatics using an indole-catalytic protocol, which is suitable for a wide range of substrates including thioarenes.
- Shi, Yao,Ke, Zhihai,Yeung, Ying-Yeung
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supporting information
p. 4448 - 4452
(2018/10/17)
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- The effects of bromine atoms on the photophysical and photochemical properties of 3-cinnamoylcoumarin derivatives
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Eight coumarin derivatives (T1-T8) with or without modification using one or two bromine atoms were synthesized through the aldol condensation reaction. Their photophysical, photochemical and electrochemical properties were investigated. It was shown that
- Sun, Zhiyuan,Wang, Yu,Fang, De-Cai,Zhao, Yuxia
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supporting information
p. 7377 - 7382
(2018/05/07)
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- DMABI tripod structures with sensing capabilities: Synthesis, characterization and fluorescence analysis
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We present herein the synthesis, and the structural and spectroscopic analysis of a non-planar tripod-shaped p-(N,N′-dimethylamino)benzyliden-1,3-indandione (DMABI) chromophore. This novel molecule is composed of a Si core with three incorporated arms, each of them contains a 1,3-indandione derivative with an electron donating (-NMe2) group, thus providing fluorescence capabilities. We prepared a DMABI arm by coupling a p-(N,N′-dimethylamino)benzaldehyde (DMAB) tripod substituted molecule with 1,3-indandione via aldol condensation. The structures of DMAB-tripods were confirmed by spectroscopic data and studied by quantum chemical calculations. Fluorescence spectroscopy was used for optical characterization. Quantum yields and the corresponding lifetimes reveal typical characteristics of conjugated derivatives. Finally, we monitored the enhancement in fluorescence intensity of compound 1 in the presence of 4-chloro-2,6-dinitroaniline (4CDNA) in the range between 0 and 20 mg L-1. We justify this enhancement by calculated energies and the distribution of the HOMO and the LUMO for DMABI-tripod and 4CDNA.
- Contreras-Cáceres, Rafael,Do?a, Manuel,López-Ramírez, Maria Rosa,Algarra, Manuel,Hierrezuelo, Jesus,Casado-Rodríguez, Miguel Angel,Sánchez-Molina, Maria,Díaz, Amelia,Campos, Bruno B.,Esteves Da Silva, Joaquim C. G.,López-Romero, Juan Manuel
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p. 2393 - 2400
(2016/03/22)
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- Aggregation-induced emission enhancement in halochalcones
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A family of push-pull fluorophores, consisting of a chalcone core decorated with electron-donating substituents and halogen atoms, was designed and synthesized. Luminescence studies were performed in solution, aggregate form and in the solid state. Although some compounds are only weakly fluorescent in solution, all are emissive in the solid state showing aggregation-induced emission enhancement. In the crystalline state, the halogen atoms are not involved in halogen bonds but their presence strongly influences the aggregation-induced emission properties of the fluorophores.
- Vaz, Patricia A. A. M.,Rocha, Jo?o,Silva, Artur M.S.,Guieu, Samuel
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supporting information
p. 8198 - 8201
(2016/10/11)
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- INHIBITORS OF KIDNEY-TYPE GLUTAMINASE, GLS-1
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The present invention relates generally to glutaminase inhibitors of Formula I, Formula II, or Formula III, as well as pharmaceutical compounds containing them and methods of their use.
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Paragraph 0124
(2016/06/28)
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- Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization
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An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.
- Song, Song,Sun, Xiang,Li, Xinwei,Yuan, Yizhi,Jiao, Ning
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supporting information
p. 2886 - 2889
(2015/06/30)
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- A facile, regioselective and controllable bromination of aromatic amines using a CuBr2/Oxone system
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A combination of cupric bromide and Oxone serves as a facile, mild and effective reagent for the bromination of aromatic amines. Primary, secondary and tertiary aromatic amines are all suitable substrates. The reaction possesses high regioselectivity and functional group tolerance, and mono- and multi-brominated products can be obtained controllably in moderate to excellent yields. The Royal Society of Chemistry 2013.
- Li, Xin-Le,Wu, Wei,Fan, Xin-Heng,Yang, Lian-Ming
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p. 12091 - 12095
(2013/09/02)
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- Novel Indanone Derivatives as Potential Imaging Probes for β-Amyloid Plaques in the Brain
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Molecular imaging probes to detect senile plaques (SPs) might help the early diagnosis of Alzheimer's disease (AD). In this study, a novel series of indanone derivatives were synthesized and characterized. In in vitro binding studies, compound 2e exhibited a Ki value of 16 nM with a human AD brain homogenate. Although they displayed relatively low affinities for 2i and 2j-with Ki values of 99 and 237 nM, respectively-the SPs in AD brain sections were positively stained by 2j. A method for in situ micro-autoradiography of AD brain was developed in this study and showed clear labeling of SPs by [125I]2i and [125I]2j. Both [125I]2i and [125I]2j had suitable lipophilicities and displayed high initial uptake and rapid clearance from the mouse brains. Furthermore, [125I]2i and [125I]2j were more stable in human brain homogenates than in mouse brain homogenates. These data suggest that such indanone derivatives might represent potential amyloid imaging agents for the detection of SPs in AD.
- Qiao, Jin-Ping,Gan, Chang-Sheng,Wang, Chen-Wei,Ge, Jin-Fang,Nan, Dou-Dou,Pan, Jian,Zhou, Jiang-Ning
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scheme or table
p. 1652 - 1662
(2012/09/21)
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- Silica-supported quinolinium tribromide: A recoverable solid brominating reagent for regioselective monobromination of aromatic amines
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Silica-supported quinolinium tribromide was synthesized and found to be an efficient, stable, and recoverable solid brominating reagent for the regioselective monobromination of aromatic amines. This protocol has advantages of high yield, mild condition and simple work-up procedure.
- Li, Zheng,Sun, Xiunan,Wang, Lue,Li, Yanbo,Ma, Yuanhong
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scheme or table
p. 496 - 501
(2010/08/06)
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- Mild, efficient, and regioselective monobromination of arylamines and phenols using [BBIm]Br3 as a new reagent
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We report here an efficient method for the synthesis and characterization of the room-temperature ionic liquid 1,3-di-n-butylimidazolium tribromide ([BBIm]Br3) (2) and its application as an efficient reagent and solvent for regioselective bromination of arylamines and phenols under mild conditions. The bromination was carried out in the absence of organic solvents, and in most cases, the only extraction solvent needed was water. The spent 1,3-di-n-butylimidazolium bromide (1) was easily recycled.
- Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
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experimental part
p. 647 - 653
(2011/02/27)
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- An efficient regioselective NBS aromatic bromination in the presence of an ionic liquid
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A simple, efficient, and rapid method was developed for high-yielding regioselective monobromination of activated aromatic compounds using NBS in combination with ionic liquid 1-butyl-1-methylimidazolium bromide ([Bmim]Br) or dioxane. The ionic liquid is recyclable and can be reused with minimal loss in the catalytic efficiency if the ionic liquid is rapidly microwaved prior to reactions.
- Pingali, Subramanya R.K.,Madhav, Monika,Jursic, Branko S.
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experimental part
p. 1383 - 1385
(2010/04/25)
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- Simple catalyst-free regio- and chemoselective monobromination of aromatics using NBS in polyethylene glycol
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NBS in polyethylene glycol has been efficiently utilized for regio- and chemoselective bromination of activated aromatics at room temperature to form the corresponding bromo products in excellent yields. Copyright Taylor & Francis Group, LLC.
- Venkateswarlu, Katta,Suneel, Kanaparthy,Das, Biswanath,Reddy, Kuravallapalli Nagabhushana,Reddy, Thummala Sreenivasulu
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experimental part
p. 215 - 219
(2009/04/07)
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- An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent/solvent under mild conditions
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1-Butyl-3-methylpyridinium tribromide, [BMPy]Br3 proves to be a highly efficient, regioselective reagent/solvent for nuclear bromination of various anilines and phenols. The synthesis and characterization of the room temperature ionic liquid [BMPy]Br3 (2) is described. The bromination was carried out in the absence of organic solvents and in most cases the only extraction solvent needed was water. The spent 1-butyl-3-methylpyridinium bromide (1) was easily recycled.
- Borikar, Sanjay P.,Daniel, Thomas,Paul, Vincent
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scheme or table
p. 1007 - 1009
(2009/05/11)
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- An efficient, rapid and regioselective nuclear bromination of aromatics and heteroaromatics with NBS using sulfonic-acid-functionalized silica as a heterogeneous recyclable catalyst
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A simple, efficient and rapid method has been developed for high-yielding regioselective nuclear monobromination of aromatic and heteroaromatic compounds using NBS in the presence of sulfonic-acid-functionalized silica at room temperature. The catalyst works under heterogeneous conditions and can be recycled.
- Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish
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p. 8693 - 8697
(2007/10/03)
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- Tetrameric DABCO-bromine: An efficient and versatile reagent for bromination of various organic compounds
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Tetrameric DABCO-bromine is a powerful brominating agent but shows reasonable selectivity with certain substrates. The selective bromination for activated aromatic compounds and alkenes is reported. Synthesis of α-bromo ketones and nitriles has also been achieved by using this reagent and the results are also reported. All products reported were obtained in good to excellent yields.
- Heravi, Majid M.,Derikvand, Fatemeh,Ghassemzadeh, Mitra
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p. 125 - 128
(2007/10/03)
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- Regioselective and high-yielding bromination of aromatic compounds using hexamethylenetetramine-bromine
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A regioselective and highly efficient method for bromination of aromatic compounds in the presence of a stoichiometric amount of hexamethylenetetramine- bromine (HMTAB) as an efficient reagent in dichloromethane is reported. The selectivity depends on the temperature and nature of the substituent on the substrate. The reactivity of this reagent was increased by supporting it to silica gel for bromination of less activated compounds.
- Heravi, Majid M.,Abdolhosseini, Nafiseh,Oskooie, Hossein A.
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p. 8959 - 8963
(2007/10/03)
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- An intriguing effect of lithium perchlorate dispersed on silica gel in the bromination of aromatic compounds by N-bromosuccinimide
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A convenient and efficient procedure for electrophilic aromatic bromination has been developed by mixing of N-bromosuccinimide and an aromatic compound at room temperature on the surface of silica gel mixed with solid anhydrous LiClO4. All of the substrates examined underwent clean electrophilic aromatic bromination in reaction times of a few minutes to afford the corresponding bromoarenes under neutral conditions in excellent yield. In the case of thiophenol, no substitution reaction occurred, and the corresponding disulfide was obtained in excellent yield.
- Bagheri, Mojtaba,Azizi, Najmedin,Saidi, Mohammad R.
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p. 146 - 149
(2007/10/03)
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- Regioselective synthesis of para-bromo aromatic compounds
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Reaction of substituted benzenerings with N-bromophthalimide, underneutral conditions, gave the corresponding bromo derivatives with a preference for the formation of the para bromoisomer over the ortho isomer. The sim pie work-up procedure minimizes loss of product and the yields are good.
- Khazaei, Ardeshir,Manesh, Abbas Amini,Safi, Vahid Reza
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p. 559 - 562
(2007/10/03)
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- N-substituted heterocycles for the treatment of hypercholesteremia, dyslipidemia and other metabolic disorders; cancer, and other diseases
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The present invention relates to certain compounds of Formula (I) which can be useful in the treatment of diseases, such as, cancer, metabolic disorders, Type 2 Diabetes, dyslipidemia and/or hyperchloesterolemia:
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- Oxime derivatives for the treatment of dyslipidemia and hypercholesteremia
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The present invention relates to compounds of Formula (I) which may be useful in the treatment of diseases, such as, metabolic disorders, dyslipidemia and/or hyperchloesterolemia: 1
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- Heterocyclic derivatives for the treatment of diabetes and other diseases
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The present invention relates to certain substituted heterocycles of Formula (I) which are useful in the treatment of diseases related to lipid and carbohydrate metabolism, such as type 2 diabetes, adipocyte differentiation, uncontrolled proliferation, such as lymphoma, Hodgkin's Disease, leukemia, breast cancer, prostate cancer or cancers in general; and inflammation, such as osteoarthritis, rheumatoid arthritis, Crohn's Disease or Inflammatory Bowel Disease.
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- Solid state nuclear bromination with N-bromosuccinimide. Part 2. Experimental and theoretical studies of reactions with some substituted benzaldehydes
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N-Bromosuccinimide reacts with aromatic aldehydes in the solid state to yield exclusively nuclear brominated products while a similar reaction in the solution phase produces a number of products under varied conditions. The reactivity and regioselectivity have been studied in terms of the energies of HOMO, HOMO-LUMO difference, reaction free energy, reaction conditions and crystal packing. Single crystal X-ray structural analysis of 3,4-dihydroxybenzaldehyde has been carried out. Crystal packing energies of some of the reactive and unreactive benzaldehydes indicate the importance of molecular bromine diffusion in the solid state.
- Sarma, Jagarlapudi A.R.P.,Nagaraju, Akula,Majumdar, Kanak K.,Samuel, Purnima M.,Das, Indira,Roy, Sujit,McGhie, Alistair J.
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p. 1119 - 1123
(2007/10/03)
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