- Thiophenol detection using an AIE fluorescent probe through self-assembly with TPE-based glycoclusters
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We describe a novel green-emitting tetraphenylethylene-dicyanomethylene-4H-pyran (TPE-DCM) based fluorescent probe (TD-1). Conjugating TPE and DCM moieties allowed TD-1 to display high selectivity for thiophenol with excellent AIE properties in aqueous so
- Dong, Lei,Chen, Guo-Rong,He, Xiao-Peng,Vidal, Sébastien
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Read Online
- Discovery of Salidroside-Derivated Glycoside Analogues as Novel Angiogenesis Agents to Treat Diabetic Hind Limb Ischemia
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Therapeutic angiogenesis is a potential therapeutic strategy for hind limb ischemia (HLI); however, currently, there are no small-molecule drugs capable of inducing it at the clinical level. Activating the hypoxia-inducible factor-1 (HIF-1) pathway in skeletal muscle induces the secretion of angiogenic factors and thus is an attractive therapeutic angiogenesis strategy. Using salidroside, a natural glycosidic compound as a lead, we performed a structure-activity relationship (SAR) study for developing a more effective and druggable angiogenesis agent. We found a novel glycoside scaffold compound (C-30) with better efficacy than salidroside in enhancing the accumulation of the HIF-1α protein and stimulating the paracrine functions of skeletal muscle cells. This in turn significantly increased the angiogenic potential of vascular endothelial and smooth muscle cells and, subsequently, induced the formation of mature, functional blood vessels in diabetic and nondiabetic HLI mice. Together, this study offers a novel, promising small-molecule-based therapeutic strategy for treating HLI.
- Liu, Caiping,Han, Jingxuan,Marcelina, Olivia,Nugrahaningrum, Dyah Ari,Huang, Song,Zou, Meijuan,Wang, Guixue,Miyagishi, Makoto,He, Yun,Wu, Shourong,Kasim, Vivi
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supporting information
p. 135 - 162
(2022/01/14)
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- Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance
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Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsymmetric biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogues were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR.
- Cheng, Bao,Zhu, Guirong,Meng, Linghua,Wu, Guolin,Chen, Qin,Ma, Shengming
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supporting information
(2021/11/22)
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- Dirhodium-Catalyzed Enantioselective B?H Bond Insertion of gem-Diaryl Carbenes: Efficient Access to gem-Diarylmethine Boranes
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The scarcity of reliable methods for synthesizing chiral gem-diarylmethine borons limits their applications. Herein, we report a method for highly enantioselective dirhodium-catalyzed B?H bond insertion reactions with diaryl diazomethanes as carbene precursors. These reactions afforded chiral gem-diarylmethine borane compounds in high yield (up to 99 % yield), high activity (turnover numbers up to 14 300), high enantioselectivity (up to 99 % ee) and showed unprecedented broad functional group tolerance. The borane compounds synthesized by this method could be efficiently transformed into diaryl methanol, diaryl methyl amine, and triaryl methane derivatives with good stereospecificity. Mechanistic studies suggested that the borane adduct coordinated to the rhodium catalyst and thus interfered with decomposition of the diazomethane, and that insertion of a rhodium carbene (generated from the diaryl diazomethane) into the B?H bond was most likely the rate-determining step.
- Huang, Ming-Yao,Li, Xiao-Yu,Su, Yu-Xuan,Yang, Liang-Liang,Zhao, Yu-Tao,Zhu, Shou-Fei
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p. 24214 - 24219
(2021/10/07)
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- AIBN initiated functionalization of the benzylic sp3 C[sbnd]H and C[sbnd]C bonds in the presence of dioxygen
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A sp3 C[sbnd]H bond functionalization and C[sbnd]C bond cleavage were realized by AIBN/O2 catalyst system, providing a series of benzophenones under mild reaction conditions. The mechanistic study shows that a peroxide intermediate is involved in this transformation, and in the case of diphenylmethanes, the sp3 C[sbnd]C bond is cleaved through the peroxide rearrangement, which might provides a new way to cleave relatively strong C[sbnd]C bond and be applied to more general C[sbnd]C bond activation.
- Hu, Yingying,Shao, Yu,Zhang, Shuwei,Yuan, Yuan,Sun, Zheng,Yuan, Yu,Jia, Xiaodong
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supporting information
(2021/02/01)
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- Synthesis, structure, and characterization of picolyl- and benzyl-linked biphenyl palladium N-heterocyclic carbene complexes and their catalytic activity in acylative cross-coupling reactions
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N-heterocyclic carbene ligands with picolyl (L1H2Br2, L3H2Br2) and benzyl (L2H2Br2, L4H2Br2) linked biphenyl backbone were synthesized and characterized. Their palladium(II) complexes [PdL1]Br2 (1), [PdL2Br2] (2), [PdL3]Br2 (3), and [PdL4Br2] (4) were synthesized by direct method using Pd(OAc)2. All complexes (1–4) were characterized by CHN analysis, electrospray ionization-MS, nuclear magnetic resonance, and single-crystal X-ray diffraction. Molecular structures confirm the distorted square planar geometry around the Pd(II) center. All of them showed good catalytic activity in acylative Suzuki cross coupling of phenyl boronic acid with benzoyl chloride to afford benzophenone in good yields.
- Muniyappan, Nalluchamy,Sabiah, Shahulhameed
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- NOVEL ARYL ETHANE DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING SAME AS ACTIVE INGREDIENT
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The present invention relates to an aryl ethene derivative, for inhibiting an estrogen-related receptor gamma (ERRγ) activity, a prodrug of same, a solvate of same, a stereoisomer of same or pharmaceutically acceptable salts of same, and a pharmaceutical
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Paragraph 0122; 0123
(2019/04/16)
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- Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
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We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
- Liu, Guangchang,Xu, Bo
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supporting information
p. 869 - 872
(2018/02/09)
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- NOVEL ARYL ETHENE DERIVATIVES AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME AS AN ACTIVE INGREDIENT
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The present invention relates to an aryl ethene derivative represented by chemical formula 1 which suppresses the activity of estrogen-related receptor gamma (ERRandgamma;), a prodrug thereof, a solvate thereof, a stereomer thereof, or a pharmaceutically acceptable salt thereof, and to a pharmaceutical composition comprising the same as an effective component. In the chemical formula 1, R^1, R^2, L and Ar are the same as defined in the detailed description of the invention.COPYRIGHT KIPO 2018
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Paragraph 0248-0250
(2018/05/03)
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- Tetraphenylethylene-based subcellular organelle viscosity probe, and preparation method and application thereof
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The invention provides a tetraphenylethylene-based subcellular organelle viscosity probe, and a preparation method and an application thereof. The subcellular organelle viscosity probe comprises a mitochondrial viscosity probe and a lysosomal viscosity probe. The preparation method mainly comprises the following steps (1) synthesis of a compound TPE-Br, (2) synthesis of a compound TPE-CHO, (3) synthesis of the mitochondrial viscosity probe, and (4) synthesis of the lysosomal viscosity probe. The synthesized viscosity probe can be used for detecting the viscosity of subcellular organelles. Thepreparation method of the tetraphenylethylene-based subcellular organelle viscosity probe is simple; the synthesized viscosity probe has good water solubility, and has no influences on the state of studied cells in the working concentration range; the viscosity probe has weak self-fluorescence background, so the imaging contrast of the subcellular organ viscosity monitoring is improved; and the viscosity probe is sensitive to the viscosity, has strong anti-interference, and has good targeting specificity to the subcellular organelles.
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Paragraph 0064; 0070; 0071; 0098; 0100-0101
(2018/09/28)
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- METHODS AND COMPOSITIONS FOR NEAR INFRARED FLUORESCENT NANODOTS WITH AGGREGATION-INDUCED EMISSION CHARACTERISTICS
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Disclosed herein is a donor-acceptor-donor (D-A-D) compound of formula I, where in the acceptors are mono-substituted tetraphenylethylene moieties. Also disclosed herein are fluorescent nanodots that comprise the compound of formula (I) and uses of said c
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Page/Page column 8; 25
(2018/03/06)
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- Strategies to Enhance the Photosensitization: Polymerization and the Donor–Acceptor Even–Odd Effect
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A particular challenge in the design of organic photosensitizers (PSs) with donor–acceptor (D-A) structures is that it is based on trial and error rather than specific rules. Now these challenges are addressed by proposing two efficient strategies to enhance the photosensitization efficiency: polymerization-facilitated photosensitization and the D-A even–odd effect. Conjugated polymers have been found to exhibit a higher 1O2 generation efficiency than their small molecular counterparts. Furthermore, PSs with A-D-A structures show enhanced photosensitization efficiency over those with D-A-D structures. Theoretical calculations suggest an enhanced intersystem crossing (ISC) efficiency by these strategies. Both in vitro and in vivo experiments demonstrate that the resulting materials can be used as photosensitizers in image-guided photodynamic anticancer therapy. These guidelines are applicable to other polymers and small molecules to lead to the development of new PSs.
- Liu, Shunjie,Zhang, Haoke,Li, Yuanyuan,Liu, Junkai,Du, Lili,Chen, Ming,Kwok, Ryan T. K.,Lam, Jacky W. Y.,Phillips, David Lee,Tang, Ben Zhong
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supporting information
p. 15189 - 15193
(2018/10/26)
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- Long wavelength excitable near-infrared fluorescent nanoparticles with aggregation-induced emission characteristics for image-guided tumor resection
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Near infrared (NIR) fluorescence imaging (700-900 nm) is a promising technology in preclinical and clinical tumor diagnosis and therapy. The availability of excellent NIR fluorescent contrast agents is still the main barrier to implementing this technolog
- Liu, Jie,Chen, Chao,Ji, Shenglu,Liu, Qian,Ding, Dan,Zhao, Dan,Liu, Bin
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p. 2782 - 2789
(2017/04/06)
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- Organic Nanocrystals with Bright Red Persistent Room-Temperature Phosphorescence for Biological Applications
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Persistent room-temperature phosphorescence (RTP) in pure organic materials has attracted great attention because of their unique optical properties. The design of organic materials with bright red persistent RTP remains challenging. Herein, we report a n
- Fateminia, S. M. Ali,Mao, Zhu,Xu, Shidang,Yang, Zhiyong,Chi, Zhenguo,Liu, Bin
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supporting information
p. 12160 - 12164
(2017/09/06)
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- Carbonylative Suzuki Coupling Reaction Catalyzed by a Hydrospirophosphorane Palladium Complex
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A Pd complex with the H-spirophosphorane ligand, PdCl2{P(OCMe2CMe2O)OC6H4NH2} (Cat. 1), was used as the catalyst in the carbonylative Suzuki coupling of substituted iodobenzenes with arylboronic acids and with sodium tetraphenylborate. Substituted diarylketones were obtained in good to excellent yields and a selectivity over 95 % under 1 atm of CO with 1.5 mol % of the catalyst. The promoting role of the H-spirophosphorane ligand in the catalytic process was evidenced. We used X-ray photoelectron spectroscopy, TEM, and 31P NMR spectroscopy to reveal that during the reaction Cat. 1 undergoes transformation into Pd complexes that bear the spirophosphorane ligand or other P ligands formed by its dealkylation and to Pd nanoparticles. All these Pd species contribute to the high productivity of the system.
- Wójcik, Przemys?aw,Sygellou, Labrini,Gniewek, Andrzej,Skar?yńska, Anna,Trzeciak, Anna
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p. 4397 - 4409
(2017/11/21)
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- P -Selective (sp2)-C-H functionalization for an acylation/alkylation reaction using organic photoredox catalysis
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p-Selective (sp2)-C-H functionalization of electron rich arenes has been achieved for acylation and alkylation reactions, respectively, with acyl/alkylselenides by organic photoredox catalysis involving an interesting mechanistic pathway.
- Pandey, Ganesh,Tiwari, Sandip Kumar,Singh, Bhawana,Vanka, Kumar,Jain, Shailja
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supporting information
p. 12337 - 12340
(2017/11/20)
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- SUBSTITUTED AMINOALKYLAZOLES AS MALARIAL ASPARTIC PROTEASE INHIBITORS
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The present invention relates to novel aminoalkylazoles acting as inhibitors of malarial protease plasmepsin II. These can be used as medicines or as constituent of medicines for the treatment of malaria infection.
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Page/Page column 34
(2017/08/01)
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- Synthesis and biological evaluation of novel 4-hydroxytamoxifen analogs as estrogen-related receptor gamma inverse agonists
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Estrogen-related receptor gamma (ERRγ) has recently been recognized as an attractive target for treating inflammation, cancer, and metabolic disorders. Herein, we discovered and demonstrated the in vitro pharmacology as well as the absorption, distribution, metabolism, excretion, and toxicity (ADMET) properties of chemical entities that could act as highly selective inverse agonists for ERRγ. The results were comparable to those for GSK5182 (4), a leading ERRγ inverse agonist ligand. Briefly, the half-maximal inhibitory concentration (IC50) range of the synthesized compounds for ERRγ was 0.1-10 μM. Impressively, compound 24e exhibited potency comparable to 4 but was more selective for ERRγ over three other subtypes: ERRα, ERRβ, and estrogen receptor α. Furthermore, compound 24e exhibited a superior in vitro ADMET profile compared to the other compounds. Thus, the newly synthesized class of ERRγ inverse agonists could be lead candidates for developing clinical therapies for ERRγ-related disorders.
- Kim, Jina,Chin, Jungwook,Im, Chun Young,Yoo, Eun Kyung,Woo, Seoyeon,Hwang, Hee Jong,Cho, Joong-Heui,Seo, Kyung-Ah,Song, Jaeyoung,Hwang, Hayoung,Kim, Kyung-Hee,Kim, Nam Doo,Yoon, Suk Kyoon,Jeon, Jae-Han,Yoon, Seung-Yun,Jeon, Yong Hyun,Choi, Hueng-Sik,Lee, In-Kyu,Kim, Seong Heon,Cho, Sung Jin
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p. 338 - 352
(2016/07/06)
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- Synthesis of Benzophenone Nucleosides and Their Photocatalytic Evaluation for [2+2] Cycloaddition in Aqueous Media
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Four benzophenone nucleosides that are para-substituted (-NH2, -NMe2, -OMe, and -Me) in relation to the carbonyl group were synthesized and characterized by their optical properties. The electron-donating character of the substituent
- Ga?, Nadine,Wagenknecht, Hans-Achim
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p. 6661 - 6668
(2015/10/29)
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- Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities
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Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of br
- Lv, Wei,Liu, Jinzhong,Skaar, Todd C.,Flockhart, David A.,Cushman, Mark
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p. 2623 - 2648
(2015/04/14)
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- Synthesis and biological evaluation of N-cyclopropylbenzamide-benzophenone hybrids as novel and selective p38 mitogen activated protein kinase (MAPK) inhibitors
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A series of hybrid molecules consisting of benzophenones and N-cyclopropyl-3-methylbenzamides were synthesized and biologically evaluated as novel p38 mitogen activated protein kinase (MAPK) inhibitors. In particular, we found that compound 10g displayed
- Heo, Jinyuk,Shin, Hanbo,Lee, Jun,Kim, Taelim,Inn, Kyung-Soo,Kim, Nam-Jung
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p. 3694 - 3698
(2015/08/11)
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- Erbium trifluoromethanesulfonate catalyzed Friedel-Crafts acylation using aromatic carboxylic acids as acylating agents under monomode-microwave irradiation
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Erbium trifluoromethanesulfonate is found to be a good catalyst for the Friedel-Crafts acylation of arenes containing electron-donating substituents using aromatic carboxylic acids as the acylating agents under microwave irradiation. An effective, rapid and waste-free method allows the preparation of a wide range of aryl ketones in good yields and in short reaction times with minimum amounts of waste.
- Tran, Phuong Hoang,Hansen, Poul Erik,Nguyen, Hai Truong,Le, Thach Ngoc
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p. 612 - 618
(2015/02/19)
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- Palladium(II)-catalyzed desulfitative synthesis of aryl ketones from sodium arylsulfinates and nitriles: Scope, limitations, and mechanistic studies
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A fast and efficient protocol for the palladium(II)-catalyzed production of aryl ketones from sodium arylsulfinates and various organic nitriles under controlled microwave irradiation has been developed. The wide scope of the reaction has been demonstrated by combining 14 sodium arylsulfinates and 21 nitriles to give 55 examples of aryl ketones. One additional example illustrated that, through the choice of the nitrile reactant, benzofurans are also accessible. The reaction mechanism was investigated by electrospray ionization mass spectrometry and DFT calculations. The desulfitative synthesis of aryl ketones from nitriles was also compared to the corresponding transformation starting from benzoic acids. Comparison of the energy profiles indicates that the free energy requirement for decarboxylation of 2,6-dimethoxybenzoic acid and especially benzoic acid is higher than the corresponding desulfitative process for generating the key aryl palladium intermediate. The palladium(II) intermediates detected by ESI-MS and the DFT calculations provide a detailed understanding of the catalytic cycle. (Figure Presented).
- Skillinghaug, Bobo,Sk?ld, Christian,Rydfjord, Jonas,Svensson, Fredrik,Behrends, Malte,S?vmarker, Jonas,Sj?berg, Per J. R.,Larhed, Mats
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p. 12018 - 12032
(2015/01/16)
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- SUBSTITUTED PYRIMIDINES
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Disclosed are substituted pyrimidines useful as HIF prolyl hydroxylase inhibitors to treat anemia and like conditions.
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Page/Page column 32
(2013/04/10)
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- SUBSTITUTED PYRIMIDINES
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The present invention relates to substituted pyrimidines useful as HIF prolyl hydroxylase inhibitors to treat anemia and like conditions.
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Page/Page column 32
(2013/04/10)
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- Synthesis of diaryl ketones via a phosphine-free Fukuyama reaction
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The synthesis of unsymmetrical diaryl ketones via the Fukuyama coupling of thioesters and organozinc reagents is described. Typically, the synthesis of diaryl ketones using this methodology provides low yields. The simple complex, Pd(dba)2, was found to convert a variety of aryl thioesters to diaryl ketones in good yields. The Royal Society of Chemistry 2011.
- Kunchithapatham, Kamala,Eichman, Chad C.,Stambuli, James P.
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p. 12679 - 12681
(2012/01/05)
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- Photochemically promoted transition metal-free cross-coupling of acylsilanes with organoboronic esters
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Intermolecular carbon-carbon bond formation between acylsilanes and organoboronic esters was achieved by photoirradiation under almost neutral, transition metal-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of acylsilanes reacted with boronic esters to give the formal B-C bond insertion intermediates, which underwent unique rearrangement to afford the cyclic α-alkoxyboronic esters. Acidic treatment of the resulting crude products under air furnished the cross-coupled ketones in good yields.
- Ito, Kazuta,Tamashima, Hiroto,Iwasawa, Nobuharu,Kusama, Hiroyuki
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supporting information; experimental part
p. 3716 - 3719
(2011/05/14)
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- Synthesis of arylketones by ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids
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The first ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids is reported. Various aliphatic and aromatic aldehydes are transformed to the corresponding arylketones. A total of 31 examples with moderate to excellent yields are presented, together with the results of an initial mechanistic investigation.
- Li, Hong,Xu, Yuan,Shi, Erbo,Wei, Wei,Suo, Xiangqiang,Wan, Xiaobing
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supporting information; experimental part
p. 7880 - 7882
(2011/08/06)
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- Aryl ketone synthesis via tandem orthoplatinated triarylphosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation
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Tandem orthoplatinated triaryl phosphite-catalyzed addition reactions of arylboronic acids with aldehydes followed by oxidation to yield aryl ketones is described. 3-Pentanone was identified as a suitable oxidant for the tandem aryl ketone formation reaction. By using microwave energy, aryl ketones were obtained in high yields with the catalyst loading as low as 0.01%.
- Liao, Yuan-Xi,Hu, Qiao-Sheng
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supporting information; experimental part
p. 6986 - 6989
(2010/11/17)
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- Pd(0)/C-catalyzed cross-couplings of acyl chlorides with triarylbismuths as atom-efficient sub-stoichiometric multi-coupling reagents
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Aromatic and hetero-aromatic acyl chlorides were efficiently cross-coupled with triarylbismuths as atom-efficient nucleophilic organometallic coupling reagents in sub-stoichiometric amounts using catalytic Pd(0)/C. Thus, the coupling reactions of various triarylbismuths with a variety of acyl chlorides furnished a plethora of both symmetrical/unsymmetrical aromatic and hetero-aromatic ketones in high yields.
- Rao, Maddali L.N.,Jadhav, Deepak N.,Venkatesh, Varadhachari
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experimental part
p. 4268 - 4271
(2009/10/26)
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- BIARYL SUBSTITUTED HETEROCYCLE INHIBITORS OF LTA4H FOR TREATING INFLAMMATION
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The present invention relates to a chemical genus of biaryl substituted heterocycle inhibitors of LTA4H (leukotriene A4 hydrolase) useful for the treatment and prevention and prophylaxis of inflammatory diseases and disorders. The compounds have general formula Ψ: An example is
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Page/Page column 62-63
(2008/06/13)
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- Discovery of 1,4-didydroxy-2-naphthoate prenyltransferase inhibitors: New drug leads for multidrug-resistant gram-positive pathogens
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Since utilization of menaquinone in the electron transport system is a characteristic of Gram-positive organisms, the 1,4-dihydroxy-2-naphthoate prenyltransferase (MenA) inhibitors 1a and 2a act as selective antibacterial agents against organisms such as methicillin-resistant Stapylococcus aureus (MRSA), Staphylococcus epidermidis (MRSE), and Mycobacterium spp. Growth of drug-resistant Gram-positive organisms was sensitive to the MenA inhibitors, indicating that menaquinone synthesis is a valid new drug target in Gram-positive organisms.
- Kurosu, Michio,Narayanasamy, Prabagaran,Biswas, Kallolmay,Dhiman, Rakesh,Crick, Dean C.
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p. 3973 - 3975
(2008/02/11)
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- Tandem catalysis: Access to ketones from aldehydes and arylboronic acids via rhodium-catalyzed addition/oxidation
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Direct cross-coupling reactions of aromatic aldehydes with arylboronic acids afforded ketones in high yields and under mild conditions in the presence of a rhodium catalyst, acetone and a base. This new reaction, involving a formal aldehyde C-H bond activation, is believed to proceed via a tandem process involving addition of the organometallic species to the aldehyde followed by oxidation by β-hydride transfer.
- Mora, Guilhem,Darses, Sylvain,Genet, Jean-Pierre
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p. 1180 - 1184
(2008/09/16)
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- Atom-efficient cross-coupling reactions of triarylbismuths with acyl chlorides under Pd(0) catalysis
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The atom-efficient cross-coupling reaction of triarylbismuths with a variety of aliphatic, aromatic, and hetero-aromatic acyl chlorides was demonstrated to afford high yields of cross-coupled ketones under palladium catalysis. The corresponding cross-coupling reaction with diacid chlorides also furnished bis-coupled ketones in good yields.
- Rao, Maddali L.N.,Venkatesh, Varadhachari,Banerjee, Debasis
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p. 12917 - 12926
(2008/03/28)
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- An atom-efficient palladium-catalyzed cross-coupling reaction of triarylbismuths with acid chlorides: synthesis of diaryl and alkyl aryl ketones
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The cross-coupling reaction of triarylbismuths with acid chlorides using a catalytic amount of PdCl2/PPh3 afforded the corresponding ketones in high yields. The reactions of aromatic and aliphatic acid chlorides occurred with atom efficiency, as 3 equiv of acid chlorides coupled effectively with 1 equiv of triarylbismuths to yield 3 equiv of the corresponding diaryl and alkyl aryl ketones.
- Rao, Maddali L.N.,Venkatesh, Varadhachari,Jadhav, Deepak N.
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p. 6975 - 6978
(2007/10/03)
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- Application of the catalytic friedel-crafts acylation reaction and regioselectivity correlations
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A correlation was found between electronic properties and regioselectivity in the Friedel-Crafts reaction of substituted phenylacetic and benzoic acids with anisole, utilising substoichiometric (down to 1 mol%) amounts of catalyst. Relative reactivities of selected catalysts for this reaction were also studied. Georg Thieme Verlag Stuttgart.
- Wilkinson, Mark C.,Saez, Fabienne,Wei, Lee Hon
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p. 1063 - 1066
(2007/10/03)
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- CHEMICAL COMPOUNDS
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The present invention relates to novel compounds with a variety of therapeutic uses, more particularly novel substituted cyclic alkylidene compounds that are particularly useful for selective estrogen receptor modulation.
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Page/Page column 39
(2008/06/13)
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- Preparation of prodrugs for selective drug delivery
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Synthesis of a chemical compound having the formula A-B-C that may serve for applications such as drug delivery where A is a chemiluminescent, moiety, B is a photochromic moiety, and C is a biologically active moiety where A-B-C may serve as a prodrug. No
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Page/Page column 101
(2010/02/11)
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- Palladium-catalyzed coupling of thiol esters with aryl and primary and secondary alkyl organoindium reagents
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Thiol esters and organoindium reagents undergo palladium-catalyzed cross-coupling under mild conditions to give ketones in moderate to excellent yields. Aryl and primary/ secondary alkyl organoindium reagents can be used as coupling partners. This method has two advantages over the cross-coupling of thiol esters with boron and tin reagents: (1) no added copper reagent is required to mediate the reaction and (2) for the case of alkyl transfer, no added base is required to activate organoindium reagents for cross-coupling as is required for the coupling of alkyl boron reagents with thiol esters.
- Fausett, Bryan W.,Liebeskind, Lanny S.
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p. 4851 - 4853
(2007/10/03)
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- Synthesis and structure-activity studies of novel orally active non-terpenoic 2,3-oxidosqualene cyclase inhibitors
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New orally active non-terpenoic inhibitors of human 2,3-oxidosqualene cyclase (hOSC) are reported. The starting point for the optimization process was a set of compounds derived from a fungicide project, which in addition to showing high affinity for OSC from Candida albicans showed also high affinity for human OSC. Common structural elements of these inhibitors are an amine residue and an electrophilic carbonyl C atom embedded in a benzophenone system, which are at a distance of about 10.7 ?. Considering that the keto moiety is in a potentially labile position, modifications of the substitution pattern at the benzophenone as well as annelated heteroaryl systems were explored. Our approach combined testing of the compounds first for increased binding affinity and for increased stability in vitro. Most promising compounds were then evaluated for their efficacy in lowering plasma total cholesterol (TC) and plasma low-density lipoprotein cholesterol (LDL-C) in hyperlipidemic hamsters. In this respect, the most promising compounds are the benzophenone derivative 1·fumarate and the benzo[d]-isothiazol 24·fumarate, which lowered TC by 40% and 33%, respectively.
- Dehmlow, Henrietta,Aebi, Johannes D.,Jolidon, Synèse,Ji, Yu-Hua,Von der Mark, Elisabeth M.,Himber, Jacques,Morand, Olivier H.
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p. 3354 - 3370
(2007/10/03)
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- Synthesis and structure-activity relationship for new series of 4-phenoxyquinoline derivatives as specific inhibitors of platelet-derived growth factor receptor tyrosine kinase
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We discovered a new series of 4-phenoxyquinoline derivatives as potent and selective inhibitors of the platelet-derived growth factor receptor (PDGFr) tyrosine kinase. We researched the highly potent and selective inhibitors on the basis of both PDGFr and epidermal growth factor receptor (EGFr) inhibitory activity. First, we found a compound, Ki6783 (1), which inhibited PDGFr autophosphorylation at 0.13 μM, but it did not inhibit EGFr autophosphorylation at 100 μM. After extensive explorations, we found the two desired compounds, Ki6896 (2) and Ki6945 (3), which are substituted by benzoyl and benzamide at the 4-position of the phenoxy group on 4-phenoxyquinoline, respectively. These inhibitory activities were 0.31 and 0.050 μM, respectively, but neither of them inhibited EGFr autophosphorylation at 100 μM. We further investigated the profile of both compounds toward various tyrosine and serine/threonine kinases. The three compounds specifically inhibited PDGFr rather than the other kinases.
- Kubo, Kazuo,Ohyama, Shin-Ichi,Shimizu, Toshiyuki,Takami, Atsuya,Murooka, Hideko,Nishitoba, Tsuyoshi,Kato, Shinichiro,Yagi, Mikio,Kobayashi, Yoshiko,Iinuma, Noriko,Isoe, Toshiyuki,Nakamura, Kazuhide,Iijima, Hiroshi,Osawa, Tatsushi,Izawa, Toshio
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p. 5117 - 5133
(2007/10/03)
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- Palladium-imidazolium-catalyzed carbonylative coupling of aryl diazonium ions and aryl boronic acids
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Palladium(II) acetate and N,N-bis-(2,6-diisopropylphenyl)dihydroimidazolium chloride (2 mol%) were used to catalyze the carbonylative coupling of aryl diazonium tetrafluoroborate salts and aryl boronic acids to form aryl ketones. Optimal conditions includ
- Andrus, Merritt B.,Ma, Yudao,Zang, Yunfu,Song, Chun
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p. 9137 - 9140
(2007/10/03)
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- Synthesis and structure-activity relationships of benzophenone hydrazone derivatives with insecticidal activity
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A broad range of benzophenone hydrazone derivatives was prepared and tested against selected chewing insect pests, allowing the analysis of structure-activity relationships. Good activity was found only when the aromatic rings were substituted at the 4-positions with an halogen atom and a triflate or perhaloalkoxy group. In contrast, a number of substituents on the hydrazone part led to active compounds, the best results being achieved with acyl-type substituents. The excellent laboratory and greenhouse activity of the best representatives was confirmed in semi-field trials against Spodoptera littoralis. ° 2001 Society of Chemical Industry.
- Boeger, Manfred,Duerr, Dieter,Gsell, Laurenz,Hall, Roger G.,Karrer, Friedrich,Kristiansen, Odd,Maienfisch, Peter,Pascual, Alfons,Rindlisbacher, Alfred
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p. 191 - 202
(2007/10/03)
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- Estrogenic triarylethylene acetic acids: Effect of structural variation on estrogen receptor affinity and estrogenic potency and efficacy in MCF-7 cells
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Triarylethylenecarboxylic acids exemplified by (E,Z)-2-{4-[1-(p- hydroxyphenyl)-2-phenyl]-1-butenyl}phenoxyacetic acid (8) are a new class of estrogen receptor (ER) ligands capable of tissue selective estrogen agonist and antagonist effects. We report the syntheses of 8 and of analogues incorporating structural features known or anticipated to facilitate ER affinity in triarylethylenes. These studies revealed that the p- hydroxyphenyl moiety, ethylenic bond, and ether oxygen of 8 were all critical for high ER affinity. Although a 1,1-bisphenolic analogue bearing the p- (oxyacetic acid) moiety on its 2-phenyl ring, 12, had low ER affinity, it exhibited estrogenic potency approaching that of 8 in MCF-7 cells. Unlike 8 which was a partial agonist with weak antagonist potency, 12 was a full agonist. A similar profile of potency/efficacy in MCF-7 cells was seen in 9, an ethylenic bond saturated analogue of 8. Growth-promoting effects of 8, 9, and 12 were fully antagonized by the antiestrogen tamoxifen, suggesting that such effects were mediated solely via ER. Thus, our studies in MCF-7 cells have confirmed the estrogenicity of 8 and have enabled identification of two analogues with favorable estrogenic potency and full estrogen efficacy. On this basis, these three (triarylethylene)acetic acids have been selected for more intensive animal studies of their extrareproductive tract estrogenic effects.
- Ruenitz, Peter C.,Bourne, Caryl S.,Sullivan, Kelly J.,Moore, Susan A.
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p. 4853 - 4859
(2007/10/03)
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