- GC-FID-based quantification of the sum of the three forms of vitamin B3 from animal liver
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Vitamin B3 (nicotinic acid, nicotinamide) is an essential water-soluble vitamin and cellular energy metabolism depends on the vitamin B3-derived cofactors. Inaccessible covalently-linked nicotinic acid in food such as maize can cause vitamin B3 deficiency in animals since maize is also deficient in tryptophan, the precursor of nicotinic acid. A sensitive and reproducible GC-FID-based method for the quantification of the sum of the three forms of vitamin B3 from animal liver was developed. Free nicotinic acid, free nicotinamide and nicotinamide moiety of NAD+/NADP+ (and their riboside precursors) were simultaneously derivatized as methyl nicotinate. Reaction time and temperature and the extraction procedure for methyl nicotinate were optimized. Starting from wild boar liver, removal of proteins, solvent exchange, derivatization, and chloroform extraction resulted in sufficient enrichment and baseline separation of methyl nicotinate. The within-laboratory reproducibility of the full procedure was determined with RSD 3 standards. The overall recovery for the full procedure was 16% but very consistent (RSD = 7%), enabling determination of apparent vitamin B3 concentrations for relative quantitative comparison.
- H?mmerle, Michael,Hekmat, Omid,Le, Minh Hien
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Read Online
- Metal analyses in environmental and pharmaceutical samples by capillary electrophoresis with methyl 3-amino-3-(pyridin-3-yl)propanoate dihydrochloride as a new ion-pairing reagent
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Separation and determination of some common metal ions was achieved with methyl 3-amino-3-( pyridin-3-yl)propanoate dihydrochloride (MAPP) as an ion-pairing reagent and pyridine as a detectable counter-ion for indirect UV detection at 254 nm. The effects of the complexing reagent and chromophore concentrations, applied voltage, and organic solvent content on the separation were investigated. The optimized separation was carried out in a running electrolyte containing 16 mM MAPP and 20 mM pyridine at pH 4.0 and was successfully applied to the qualitative and quantitative analysis of Li +, Na+, Mg2+, Ca2+, Ba2+, Ni2+, and Zn2+ in pharmaceutical vitamin preparations and various water samples.
- Belin, Gamze Kavran,Guelacar, Fazil Osman
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Read Online
- Photorelease of pyridyl esters in organometallic Ru(II) arene complexes
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New Ru(II) arene complexes of formula [(η6-p-cym)Ru(N-N)(X)]2+ (where p-cym = para-cymene, N-N = 2,2′-bipyrimidine (bpm) or 2,2′-bipyridine (bpy) and X = m/p-COOMe-Py, 1-4) were synthesised and characterized, including the molecular structure of complexes [(η6-p-cym)Ru(bpy)(m-COOMe-Py)]2+ (3) and [(η6-p-cym)Ru(bpy) (p-COOMe-Py)]2+ (4) by single-crystal X-ray diffraction. Complexes 1-4 are stable in the dark in aqueous solution over 48 h and photolysis studies indicate that they can photodissociate the monodentate m/p-COOMe-Py ligands selectively with yields lower than 1%. DFT and TD-DFT calculations (B3LYP/LanL2DZ/6-31G??) performed on singlet and triplet states pinpoint a low-energy triplet state as the reactive state responsible for the selective dissociation of the monodentate pyridyl ligands.
- Habtemariam, Abraha,Garino, Claudio,Ruggiero, Emmanuel,Castro, Silvia Alonso-De,Mareque-Rivas, Juan C.,Salassa, Luca
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- Minisci-Type Alkylation of N-Heteroarenes by N-(Acyloxy)phthalimide Esters Mediated by a Hantzsch Ester and Blue LED Light
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A synthetic method that enables the Hantzsch ester-mediated Minisci-type C2-alkylation of quinolines, isoquinolines and pyridines by N-(acyloxy)phthalimide esters (NHPI) under blue LED (light emitting diode) light (456 nm) is described. Achieved under mild reaction conditions at room temperature, the metal-free synthetic protocol was shown to be applicable to primary, secondary and tertiary NHPIs to give the alkylated N-heterocyclic products in yields of 21–99%. On introducing a chiral phosphoric acid, an asymmetric version of the reaction was also realised and provided product enantiomeric excess (ee) values of 53–99%. The reaction mechanism was delineated to involve excitation of an electron-donor acceptor (EDA) complex, formed from weak electrostatic interactions between the Hantzsch ester and NHPI, which generates the posited radical species of the redox active ester that undergoes addition to the N-heterocycle.
- Kyne, Sara Helen,Li, Jiacheng,Siang Tan, Suan,Wai Hong Chan, Philip
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supporting information
(2022/01/11)
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- GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington's Disease-Related Phenotypes
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GPR52 is an orphan G protein-coupled receptor (GPCR) that has been recently implicated as a potential drug target of Huntington's disease (HD), an incurable monogenic neurodegenerative disorder. In this research, we found that striatal knockdown of GPR52 reduces mHTT levels in adult HdhQ140 mice, validating GPR52 as an HD target. In addition, we discovered a highly potent and specific GPR52 antagonist Comp-43 with an IC50 value of 0.63 μM by a structure-activity relationship (SAR) study. Further studies showed that Comp-43 reduces mHTT levels by targeting GPR52 and promotes survival of mouse primary striatal neurons. Moreover, in vivo study showed that Comp-43 not only reduces mHTT levels but also rescues HD-related phenotypes in HdhQ140 mice. Taken together, our study confirms that inhibition of GPR52 is a promising strategy for HD therapy, and the GPR52 antagonist Comp-43 might serve as a lead compound for further investigation.
- Wang, Congcong,Zhang, Yu-Fang,Guo, Shimeng,Zhao, Quan,Zeng, Yanping,Xie, Zhicheng,Xie, Xin,Lu, Boxun,Hu, Youhong
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p. 941 - 957
(2020/11/30)
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- Highly Chemoselective Deoxygenation of N-Heterocyclic N-Oxides Using Hantzsch Esters as Mild Reducing Agents
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Herein, we disclose a highly chemoselective room-temperature deoxygenation method applicable to various functionalized N-heterocyclic N-oxides via visible light-mediated metallaphotoredox catalysis using Hantzsch esters as the sole stoichiometric reductant. Despite the feasibility of catalyst-free conditions, most of these deoxygenations can be completed within a few minutes using only a tiny amount of a catalyst. This technology also allows for multigram-scale reactions even with an extremely low catalyst loading of 0.01 mol %. The scope of this scalable and operationally convenient protocol encompasses a wide range of functional groups, such as amides, carbamates, esters, ketones, nitrile groups, nitro groups, and halogens, which provide access to the corresponding deoxygenated N-heterocycles in good to excellent yields (an average of an 86.8% yield for a total of 45 examples).
- An, Ju Hyeon,Kim, Kyu Dong,Lee, Jun Hee
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supporting information
p. 2876 - 2894
(2021/02/01)
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- Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions
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Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is
- Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee
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supporting information
p. 3735 - 3742
(2021/05/04)
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- Method for preparing carboxylic ester compounds by oxidizing and breaking carbon-carbon bonds of secondary alcohol compounds
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The invention discloses a method for preparing carboxylic ester compounds by oxidizing and breaking carbon-carbon bonds of secondary alcohol compounds. The method comprises the following steps: adding a secondary alcohol compound, an additive and a nitrogen-doped mesoporous carbon loaded monatomic catalyst into a fatty primary alcohol solvent, putting into a pressure container, sealing, introducing oxygen source gas with a certain pressure, controlling the pressure of the oxygen source gas to be 0.1-1 MPa and the reaction temperature to be 80-150 DEG C, and obtaining a product after the reaction to be the carboxylic ester compound. The nitrogen-doped mesoporous carbon-loaded monatomic catalyst adopted by the invention is high in activity, the highest separation yield of the carboxylic ester compound as a reaction product reaches 99%, the method is wide in application range, the reaction conditions are easy to control, the catalyst can be recycled, the post-treatment is simple, and the method is suitable for industrial production.
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Paragraph 0074-0075; 0092
(2021/06/02)
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- Metal-Free Heterogeneous Semiconductor for Visible-Light Photocatalytic Decarboxylation of Carboxylic Acids
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A suitable protocol for the photocatalytic decarboxylation of carboxylic acids was developed with metal-free ceramic boron carbon nitrides (BCN). With visible light irradiation, BCN oxidize carboxylic acids to give carbon-centered radicals, which were trapped by hydrogen atom donors or employed in the construction of the carbon-carbon bond. In this system, both (hetero)aromatic and aliphatic acids proceed the decarboxylation smoothly, and C-H, C-D, and C-C bonds are formed in moderate to high yields (35 examples, yield up to 93%). Control experiments support a radical process, and isotopic experiments show that methanol is employed as the hydrogen atom donor. Recycle tests and gram-scale reaction elucidate the practicability of the heterogeneous ceramic BCN photoredox system. It provides an alternative to homogeneous catalysts in the valuable carbon radical intermediates formation. Moreover, the metal-free system is also applicable to late-stage functionalization of anti-inflammatory drugs, such as naproxen and ibuprofen, which enrich the chemical toolbox.
- Shi, Jiale,Yuan, Tao,Zheng, Meifang,Wang, Xinchen
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p. 3040 - 3047
(2021/03/09)
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- Synthesis of aspidodispermine via pericyclic framework reconstruction
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A divergent approach to the pyrroloquinoline scaffold as present in the class of Aspidosperma alkaloids was developed. As a case study, abundant and renewable nicotinic acid was transformed via pericyclic framework reconstruction into aspidodispermine, a unique member of pyrroloquinoline alkaloids. The sequence comprises a [2 + 2]-photocycloaddition, a Ramberg-B?cklund contraction, and a strain-promoted formal electrocyclic rearrangement of a bicyclo[2.2.0]hexene and is potentially extendable to pyrroloindole scaffolds as present in the ibophyllidine alkaloids.
- Reu?, Franziska,Heretsch, Philipp
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supporting information
p. 3956 - 3959
(2020/05/19)
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- Tetraphenyl ethylene Schiff base Al fluorescent probe and preparation method and application thereof
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The invention belongs to the field of fluorescent molecular probes, and discloses a tetraphenyl ethylene Schiff base Al fluorescent probe and a preparation method and application thereof. The preparation method comprises the following steps: dissolving 4-hydroxytetraphenyl ethylene and hexamethylenetetramine in a mixed solvent of acetic acid and trifluoroacetic acid for a reaction to obtain afirst intermediate product 4-hydroxy-5-aldehyde tetraphenyl ethylene, dissolving nicotinic acid in a methanol solvent, dropwise adding acetyl chloride into the solution, carrying out a reaction process to obtain a second intermediate product methyl nicotinate, dissolving the second intermediate product in a methanol solvent, adding hydrazine hydrate into the solution, carrying out a reaction process to obtain a third intermediate product nicotinamide, dissolving the first intermediate product and the third intermediate product in an ethanol solvent, and carrying out a reaction process to obtain the tetraphenyl ethylene Schiff base Al fluorescent probe. The fluorescent probe has specific selectivity on Al, and can be used for identifying Al in vitro, the fluorescence signal is basically not changed when acting with other common ions, the sensitivity is high, and the detection limit is low.
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Paragraph 0049; 0067; 0070
(2020/05/02)
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- Synthesis method of 3-chloromethylpyridine hydrochloride
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The invention belongs to the field of organic chemistry, and specifically relates to a synthesis method of 3-chloromethylpyridine hydrochloride. The synthesis method comprises the following steps: (1)taking 3-methylpyridine as a raw material and water as a solvent, oxidizing 3-methylpyridine into 3-picolinic acid by potassium permanganate, wherein the molar ratio of 3-methylpyridine to potassiumpermanganate is 1: (2.1-2.3); maintaining the oxidation temperature in a range of 85-90 DEG C, heating for 30 minutes, adjusting the reaction liquid to be acidic after the reaction is finished, and then cooling and filtering to obtain 3-picolinic acid; (2) generating methyl 3-picolinate from 3-picolinic acid and methanol under an acidic condition, wherein the molar ratio of 3-picolinic acid to methanol is 1: 1.3; (3) reducing methyl 3-picolinate into 3-pyridylcarbinol; and (4) reacting the 3-pyridylcarbinol with thionyl chloride to obtain the target product 3-chloromethylpyridine hydrochloride, wherein the molar ratio of the 3-pyridylcarbinol to the thionyl chloride is 1: (1.1-1.3).
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Paragraph 0020; 0022; 0025; 0027; 0030; 0032
(2020/05/05)
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- Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents
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Thalidomide and its analogs are immunomodulatory drugs that inhibit the production of certain inflammatory mediators associated with cancer. In the present work, a new series of thalidomide analogs was designed and synthesized to obtain new effective antitumor immunomodulatory agents. The synthesized compounds were evaluated for their cytotoxic activities against a panel of four cancer cell lines (HepG-2, HCT-116, PC3 and MCF-7). Compounds 33h, 33i, 42f and 42h showed strong potencies against all tested cell lines with IC50 values ranging from 14.63 to 49.90 μM comparable to that of thalidomide (IC50 values ranging from 32.12 to 76.91 μM). The most active compounds were further evaluated for their in vitro immunomodulatory activities via estimation of human tumor necrosis factor alpha (TNF-α), human caspase-8 (CASP8), human vascular endothelial growth factor (VEGF), and nuclear factor kappa-B P65 (NF-κB P65) in HCT-116 cells. Thalidomide was used as a positive control. Compounds 33h and 42f showed a significant reduction in TNF-α. Furthermore, compounds 33i and 42f exhibited significant elevation in CASP8 levels. Compounds 33i and 42f inhibited VEGF. In addition, compound 42f showed significant decrease in levels of NF-κB p65. Moreover, apoptosis and cell cycle tests of the most active compound 42f, were performed. The results indicated that compound 42f significantly induce apoptosis in HCT-116 cells and arrest cell cycle at the G2/M phase.
- El-Zahabi, Mohamed Ayman,Sakr, Helmy,El-Adl, Khaled.,Zayed, Mohamed,Abdelraheem, Adel S.,Eissa, Sally I.,Elkady, Hazem,Eissa, Ibrahim H.
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- Pd/C-Catalyzed methoxycarbonylation of aryl chlorides
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A new protocol for the methoxycarbonylation of aryl chlorides has been developed. Various methyl benzoates were produced in good to excellent yields. Several parameters are crucial for the success of this procedure: 1) the usage of LiOMe as the base or co-nucleophile which facilitate the carbonylative transformation; 2) employing Pd/C as the catalyst to prevent the palladium reduced by MeOH and subsequent agglomerate; 3) CO concentration, excessive CO concentration will directly lead to the termination of the reaction.
- Ai, Han-Jun,Franke, Robert,Wu, Xiao-Feng
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- Nickel-catalyzed carboxylation of aryl and heteroaryl fluorosulfates using carbon dioxide
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The development of efficient and practical methods to construct carboxylic acids using CO2 as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO2 is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed.
- Ma, Cong,Zhao, Chuan-Qi,Xu, Xue-Tao,Li, Zhao-Ming,Wang, Xiang-Yang,Zhang, Kun,Mei, Tian-Sheng
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p. 2464 - 2467
(2019/04/10)
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- A novel coumarin-based fluorescence chemosensor for Al3+ and its application in cell imaging
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As an efficient turn-on fluorescent chemosensor for Al3+, a new coumarin derivative (CND) has been designed and synthesized by the condensation of 8-formyl-7-hydroxycoumarin with niacin hydrazide. The spectroscopic studies revealed that the sensor CND exhibited a remarkable fluorescence enhancement towards Al3+ with high selectivity and sensitivity in EtOH-HEPES (95:5, v/v, pH = 7.40), which was attributed to the photoinduced electron transfer (PET) and –C[dbnd]N isomerization mechanism. Fluorescence titration calculations data showed that the detection limit and the association constants of CND for Al3+ were found to be 2.51 × 10?7 M and 9.64 × 104 M?1, respectively. The results of experiments, including Job's plot, 1H NMR titration and ESI-MS, revealed that the stoichiometric binding between CND and Al3+ was 1:1. The investigations of the pH dependency of CND for Al3+ detection, and the cell imaging suggested the sensor CND could be promisingly applied for the recognition of Al3+ in biological cells.
- Zhu, Guohua,Huang, Yang,Wang, Chun,Lu, Linxia,Sun, Tongming,Wang, Miao,Tang, Yanfeng,Shan, Doudou,Wen, Shuijin,Zhu, Jinli
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p. 105 - 110
(2018/11/24)
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- Development of novel liver?X?receptor modulators based on a 1,2,4-triazole scaffold
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Liver X Receptor (LXR) agonists have been reported as a potential treatment for atherosclerosis, Alzheimer's disease and hepatitis C virus (HCV) infection. We have designed and synthesized a series of potent compounds based on a 1,2,4-triazole scaffold as novel LXR modulators. In cell-based cotransfection assays these compounds generally functioned as LXR agonists and we observed compounds with selectivity towards LXRα (7-fold) and LXRβ (7-fold) in terms of potency. Assessment of the effects of selected compounds on LXR target gene expression in HepG2 cells revealed that compounds 6a-b and 8a-b behaved as inverse agonists on FASN expression even though they were agonists in the LXRα and LXRβ cotransfection assays. Interestingly, these compounds had no effect on the expression of SREBP-1c confirming a unique LXR modulator pharmacology. Molecular docking studies and evaluation of ADME properties in-silico show that active compounds possess favorable binding modes and ADME profiles. Thus, these compounds may be useful for in vivo characterization of LXR modulators with unique profiles and determination of their potential clinical utility.
- Goher, Shaimaa S.,Griffett, Kristine,Hegazy, Lamees,Elagawany, Mohamed,Arief, Mohamed M.H.,Avdagic, Amer,Banerjee, Subhashis,Burris, Thomas P.,Elgendy, Bahaa
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supporting information
p. 449 - 453
(2019/01/04)
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- A 3 - chloromethyl pyridine hydrochloride synthetic method
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The invention belongs to the field of organic chemistry, and in particular relates to a 3 - chloromethyl pyridine hydrochloride synthetic method, comprises the following steps: (1) to 3 - methyl pyridine as raw materials, takes water as a solvent, the potassium permanganate oxide it to 3 - pyridine carboxylic acid, wherein 3 - methyl pyridine with potassium permanganate in a molar ratio of 1: 2.1 - 2.3, the oxidation temperature to maintain the 85 - 90 °C, heating 30 min, the reaction end the reaction liquid is adjusted to be acidic, and then cooling and filtering to obtain 3 - pyridine carboxylic acid; (2) 3 - pyridine carboxylic acid with methanol under acidic conditions to produce the 3 - pyridine carboxylic acid methyl ester, wherein the 3 - pyridine carboxylic acid with methanol in a molar ratio of 1: 1.3; (3) reducing 3 - pyridine carboxylic acid methyl ester as the 3 - pyridine methanol; (4) 3 - pyridine methanol with thionyl chloride reaction to obtain the target product 3 - chloromethyl pyridine hydrochloride, 3 - pyridine methanol with thionyl chloride in a molar ratio of 1: 1.1 - 1.3.
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Paragraph 0022; 0025; 0027; 0032
(2019/05/28)
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- Hydrazide compounds
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The invention discloses hydrazide compounds. The compounds are characterized by having a structure represented by a formula I shown in the description, wherein Ar1 and Ar2 are each independently selected from the group consisting of aryl, azinyl, piperazinyl, pyrazolyl, imidazolyl, pyrrolyl, phenyl, naphthyl, thiazolyl, thienyl, furyl, aryl, phenyl, piperazinyl, piperidinyl, piperazinyl, and-C13H9represented by a formula 9 shown in the description, only one of the Ar1 and the Ar2 is phenyl, the Ar1 has m substituents R1, Ar2 has n substituents R2, m=0 to 3, and n=0 to 3; and if the formula Ihas a plurality of substituents R1 and R2, the plurality of substituents R1 and R2 are independent with one another, can select the same substituents or different substituents, and the R1 and the R2 are each independently selected from the group consisting of halogen, hydroxyl, cyano, C1-C3 alkyl, C1-C3 alkoxy, amino, C1-C3 alkyl substituted amino, C1-C3 alkyl disubstituted amino, perfluoro C1-C3alkyl and fluoro substituted C1-C3 alkoxy.
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Paragraph 0088; 0100; 0102; 0103
(2019/10/01)
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- Design, synthesis and biological evaluation of novel copper-chelating acetylcholinesterase inhibitors with pyridine N-benzylpiperidine fragments
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Cholinergic depletion is the direct cause of disability and dementia among AD patients. AChE is a classical and key target of cholinergic disorders. Some new inhibitors of AChE combining pyridine, acylhydrazone and N-benzylpiperidine fragments were developed in this work. The hit structure was optimized to yield the compound 21 with an IC50 value of 6.62 nM against AChE, while almost no inhibitory effect against BChE. ADMET predictions and PAMPA permeability evaluation showed good drug-like property. The higher activity with an intermediate alkyl chain substitution indicates a new binding mode of inhibitor with AChE. This finding provides new insights into the binding mechanism and is helpful for discovery of novel high-activity AChE inhibitors.
- Zhou, Yeheng,Sun, Wei,Peng, Jiale,Yan, Hui,Zhang, Li,Liu, Xingyong,Zuo, Zhili
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supporting information
(2019/10/08)
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- Imine salt derivative, preparation method thereof and preparation method of nicotine
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The invention discloses an imine salt derivative, a preparation method thereof and a preparation method of nicotine. The preparation method of nicotine includes the steps of: adding an imine salt derivative shown as general formula (I) or (II) in the specification and a reducing agent into a solvent for reaction to prepare a racemic nicotine solution; adding a second quenching agent into the racemic nicotine solution to obtain a nicotine precursor solution; and adding an extracting agent into the nicotine precursor solution, conducting reduced pressure concentration, and performing drying andremoving the solvent, thus obtaining nicotine. According to the invention, through the imine salt derivative intermediate synthesized for the first time and the use of the cheap reducing agent, the intermediate is reduced under a relatively mild condition to obtain racemic nicotine. Compared with the existing nicotine synthesis process, the method has the advantages of mild synthesis process conditions, simple equipment requirement, high product purity and high synthesis rate, and is particularly suitable for industrial production.
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Paragraph 0089-0092
(2020/01/12)
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- Efficient and Recyclable RuCl3 ? 3H2O Catalyst Modified with Ionic Diphosphine for the Alkoxycarbonylation of Aryl Halides
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A series of ionic (mono-/di-)phosphines (L2, L4, and L6) with structural similarity and their corresponding neutral counterparts (L1, L3, and L5) were applied to modulate the catalytic performance of RuCl3 ? 3H2O. With the involvement of the ionic diphosphine (L4), in which the two phosphino-fragments were linked by butylene group, RuCl3 ? 3H2O with advantages of low cost, robustness, and good availability was found to be an efficient and recyclable catalyst for the alkoxycarbonylation of aryl halides. The L4-based RuCl3 ? 3H2O system corresponded to the best conversion of PhI (96 %) along with 99 % selectivity to the target product of methyl benzoate as well as the good generality to alkoxycarbonylation of different aryl halides (ArX, X=I and Br) with alcohols MeOH, EtOH, i-PrOH and n-BuOH. The electronic and steric effects of the applied phosphines, which were analyzed by the 31P NMR for 1J31P-77Se1J measurement and single-crystal X-ray diffraction, were carefully co-related to the performance RuCl3 ? 3H2O catalyst. In addition, the L4-based RuCl3 ? 3H2O system could be recycled successfully for at least eight runs in the ionic liquid [Bmim]PF6.
- Zhou, Qing,Liu, Lei,Guo, Wen-Di,Liang, Wen-Yu,Lu, Yong,Liu, Ye
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p. 166 - 172
(2019/02/01)
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- Structure-Guided Synthesis and Mechanistic Studies Reveal Sweetspots on Naphthyl Salicyl Hydrazone Scaffold as Non-Nucleosidic Competitive, Reversible Inhibitors of Human Ribonucleotide Reductase
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Ribonucleotide reductase (RR), an established cancer target, is usually inhibited by antimetabolites, which display multiple cross-reactive effects. Recently, we discovered a naphthyl salicyl acyl hydrazone-based inhibitor (NSAH or E-3a) of human RR (hRR) binding at the catalytic site (C-site) and inhibiting hRR reversibly. We herein report the synthesis and biochemical characterization of 25 distinct analogs. We designed each analog through docking to the C-site of hRR based on our 2.7 ? X-ray crystal structure (PDB ID: 5TUS). Broad tolerance to minor structural variations preserving inhibitory potency is observed. E-3f (82% yield) displayed an in vitro IC50 of 5.3 ± 1.8 μM against hRR, making it the most potent in this series. Kinetic assays reveal that E-3a, E-3c, E-3t, and E-3w bind and inhibit hRR through a reversible and competitive mode. Target selectivity toward the R1 subunit of hRR is established, providing a novel way of inhibition of this crucial enzyme.
- Huff, Sarah E.,Mohammed, Faiz Ahmad,Yang, Mu,Agrawal, Prashansa,Pink, John,Harris, Michael E.,Dealwis, Chris G.,Viswanathan, Rajesh
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supporting information
p. 666 - 680
(2018/02/16)
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- Development of N-Doped Carbon-Supported Cobalt/Copper Bimetallic Nanoparticle Catalysts for Aerobic Oxidative Esterifications Based on Polymer Incarceration Methods
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Heterogeneous nitrogen-doped carbon-incarcerated cobalt/copper bimetallic nanoparticle (NP) catalysts, prepared from nitrogen-containing polymers, were developed, and an efficient catalytic process for aerobic oxidative esterification was achieved in the presence of a low loading (1 mol %) of catalyst that could be reused and easily reactivated. This protocol enabled diverse conditions for the bimetallic NP formation step to be screened, and significant rate acceleration by inclusion of a copper dopant was discovered. The catalytic activity of the bimetallic Co/Cu catalysts is much higher than that for cobalt catalysts reported to date and is even comparable with noble-metal NP catalysts.
- Yasukawa, Tomohiro,Yang, Xi,Kobayashi, Shu
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supporting information
p. 5172 - 5176
(2018/09/12)
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- Oxalic acid as the: In situ carbon monoxide generator in palladium-catalyzed hydroxycarbonylation of arylhalides
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An efficient palladium-catalyzed hydroxycarbonylation reaction of arylhalides using oxalic acid as a CO source has been developed. The reaction features high safety, low catalyst loading, and a broad substrate scope, and provides a safe and tractable approach to access a variety of aromatic carboxylic acid compounds. Mechanistic studies revealed the decomposition pattern of oxalic acid.
- Shao, Changdong,Lu, Ailan,Wang, Xiaoling,Zhou, Bo,Guan, Xiaohong,Zhang, Yanghui
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supporting information
p. 5033 - 5040
(2017/07/10)
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- Heterogeneous cobalt catalysts for selective oxygenation of alcohols to aldehydes, esters and nitriles
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Efficient and green oxygenation of alcohols to the corresponding aldehydes, esters and nitriles was developed with high selectivity. Functional alcohols, including some heterocyclic and allylic alcohols can be oxygenated to the corresponding aldehydes, esters and nitriles respectively. Moreover, the catalyst can be recycled and reused without significant deactivation. Noteworthy, the Co@NC (800-2h) catalyzed oxygenation of alcohols can be regulated easily by changing the reaction conditions, and then the corresponding aldehydes, esters and nitriles can be obtained in high yields respectively.
- Mao, Fei,Qi, Zhengliang,Fan, Haipeng,Sui, Dejun,Chen, Rizhi,Huang, Jun
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p. 1498 - 1503
(2017/01/18)
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- Efficient and selective palladium-catalyzed direct oxidative esterification of benzylic alcohols under aerobic conditions
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A highly efficient palladium-catalyzed approach for the direct oxidative esterification of benzylic alcohols with methanol and long-chain aliphatic alcohols under mild conditions has been achieved. This practical catalyst system exhibits a broad substrate scope and good functional group tolerance. Catalytic amount of Bi(OTf)3 is used as co-catalyst to improve the activity and selectivity of the reactions. A variety of esters are obtained in yields of 43–96%.
- Hu, Yongke,Li, Bindong
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p. 7301 - 7307
(2017/11/29)
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- NOVEL PYRIDINIUM COMPOUNDS
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The present invention relates to novel pyridinium compounds, their isomers, steroisomers, atropisomers, conformers, tautomers, polymorphs, hydrates and solvates. The present invention also encompasses process for preparing novel compounds and pharmaceutical composition of said compounds. The invention further relates to the use of the above mentioned compounds for the preparation of medicament for use as pharmaceuticals.
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Page/Page column 21
(2016/10/31)
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- Oxidative Esterification of Aromatic Aldehydes Using Polymer-Supported Green Bromine
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A facile one-pot green chemical conversion of aromatic aldehydes to alkyl esters is described using polymer-supported bromine chloride resin in the presence of potassium carbonate at room temperature. This eco-friendly methodology with simple workup procedure and recovery and recyclability of the resin makes the transformation simple and efficient.
- Sridhar,Swarnalakshmi,Selvaraj
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p. 1344 - 1348
(2016/06/01)
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- NOVEL SINGLE STEP ESTERIFICATION PROCESS OF ALDEHYDES USING A HETEROGENEOUS CATALYST
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The present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using a heterogeneous catalyst with high yields. More particularly, the present invention relates to a novel simple, efficient and single-step process for esterification of aldehydes using Titanium superoxide with greater than 80% yields.
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Page/Page column 16; 20
(2016/06/20)
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- Development of Allosteric Hydrazide-Containing Class i Histone Deacetylase Inhibitors for Use in Acute Myeloid Leukemia
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One of the biggest hurdles yet to be overcome for the continued improvement of histone deacetylase (HDAC) inhibitors is finding alternative motifs equipotent to the classic and ubiquitously used hydroxamic acid. The N-hydroxyl group of this motif is highly subject to sulfation/glucoronidation-based inactivation in humans; compounds containing this motif require much higher dosing in clinic to achieve therapeutic concentrations. With the goal of developing a second generation of HDAC inhibitors lacking this hydroxamate, we designed a series of potent and selective class I HDAC inhibitors using a hydrazide motif. These inhibitors are impervious to glucuronidation and demonstrate allosteric inhibition. In vitro and ex vivo characterization of our lead analogues' efficacy, selectivity, and toxicity profiles demonstrate that they possess low nanomolar activity against models of acute myeloid leukemia (AML) and are at least 100-fold more selective for AML than solid immortalized cells such as HEK293 or human peripheral blood mononuclear cells.
- McClure, Jesse J.,Zhang, Cheng,Inks, Elizabeth S.,Peterson, Yuri K.,Li, Jiaying,James Chou
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p. 9942 - 9959
(2016/11/19)
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- Ultrasound-Assisted Methyl Esterification of Carboxylic Acids ACatalyzed by Polymer-Supported Triphenylphosphine
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A convenient and efficient sonochemical method for methyl esterification of carboxylic acids catalyzed by polymer-supported triAphenylphosphine (PS-Ph3P) is reported. In the presence of 1:0.1:2 molar ratio of 2,4,6-trichloro-1,3,5-triazine/PS-Ph3P/Na2CO3, methyl esters of various carboxylic acids bearing reactive hydroxyl groups as well as acid-or base-labile functionalities could be rapidly prepared (within 10-20 min) in good to excellent yields without necessity to pre-activate the acids. Using the polymer-bound phosphine also allows easy isolation of the products which, in most of the cases, were obtained in high purities without column chromatography.
- Jaita, Subin,Phakhodee, Wong,Pattarawarapan, Mookda
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p. 2006 - 2008
(2015/09/01)
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- BENZENE SULFONAMIDES AS CCR9 INHIBITORS
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The present invention relates to compounds useful as CCR9 modulators, to compositions containing them, to methods of making them, and to methods of using them. In particular, the present invention relates to compounds capable of modulating the function of the CCR9 receptor by acting as partial agonists, antagonists or inverse agonists. Such compounds may be useful to treat, prevent or ameliorate a disease or condition associated with CCR9 activation, including inflammatory and immune disorder diseases or conditions such as inflammatory bowel diseases (IBD).
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Page/Page column 81; 82
(2015/07/15)
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- Titanium superoxide-a stable recyclable heterogeneous catalyst for oxidative esterification of aldehydes with alkylarenes or alcohols using TBHP as an oxidant
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Titanium superoxide efficiently catalysed the oxidative esterification of aldehydes with alkylarenes or alcohols, under truly heterogeneous conditions, to afford the corresponding benzyl and alkyl esters in excellent yields. Mechanistic studies have established that this "one pot" direct oxidative esterification process proceeds through a radical pathway, proven by a FTIR spectral study of a titanium superoxide-aldehyde complex as well as spin trapping experiments with TEMPO. The intramolecular version of this protocol has been successfully demonstrated in the concise synthesis of 3-butylphthalide, an anti-convulsant drug.
- Dey, Soumen,Gadakh, Sunita K.,Sudalai
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p. 10631 - 10640
(2015/11/17)
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- A Strained Disilane-Promoted Carboxylation of Organic Halides with CO2 under Transition-Metal-Free Conditions
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By using a strained four-membered ring disilane (3,4-benzo-1,1,2,2-tetraethyldisilacyclobutene) and CsF, a wide range of aryl, alkenyl, alkynyl, benzyl, allyl, and alkyl halides was successfully carboxylated under an ambient CO2 atmosphere (CO2 balloon) at room temperature within 2 h. In this carboxylation, a highly reactive silyl anion, which is generated from the disilane and CsF, is a key to facilitating the formation of a carbanion equivalent. The resulting anionic species can be trapped with CO2 to produce carboxylic acids with high efficiency.
- Mita, Tsuyoshi,Suga, Kenta,Sato, Kaori,Sato, Yoshihiro
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supporting information
p. 5276 - 5279
(2015/11/18)
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- Silica supported palladium-phosphine as a reusable catalyst for alkoxycarbonylation and aminocarbonylation of aryl and heteroaryl iodides
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Silica-supported palladium phosphine complexes were prepared for alkoxycarbonylation and aminocarbonylation of aryl iodides. These catalysts were highly efficient for the carbonylation of unprotected hydroxy-aryl, amino-aryl, iodoindole and iodopyrazole. The carbonylation of unprotected iodopyrazole is challenging and their carbonylation was achieved for the first and obtained corresponding carbonylative products are biologically active. The applicability of developed protocols tolerates wide range of functional groups with excellent yields. The catalyst was easily recovered and shows significant recyclability up to five consecutive cycles without loss in its catalytic activity and selectivity. The prepared catalysts were characterized by different techniques such as FEG-SEM, EDS, FT-IR, XPS and ICP-AES spectroscopy.
- Mane, Rajendra Shivaji,Sasaki, Takehiko,Bhanage, Bhalchandra Mahadeo
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p. 94776 - 94785
(2015/11/24)
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- Bis azide-triphenylphosphine as a reagent for esterification at room temperature
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Modified Staudinger reaction is a well-established reaction for the amide synthesis from organic azides and carboxylic acids in the presence of phosphorous reagents. In contrary to this, it is notable that bis azide in the presence of triethylphosphite or trimethylphosphite does not afford the expected bis amides but affords the ethyl or methyl esters of the carboxylic acids respectively. This serendipitous observation when further investigated results in the discovery of bis azide-triphenylphosphine as an efficient reagent for esterification at room temperature.
- Dinesh, Murugan,Archana, Sivasubramaniyan,Ranganathan, Raja,Sathishkumar, Murugan,Ponnuswamy, Alagusundaram
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supporting information
p. 6975 - 6979
(2015/11/27)
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- Anion-Binding Catalysis by Electron-Deficient Pyridinium Cations
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A new activation principle in organocatalysis is presented: halide binding through Coulombic interactions. This mode of catalysis was realized by using 3,5-di(carbomethoxy)pyridinium ions that carry an additional electron-withdrawing substituent on the nitrogen atom, for example, pentafluorobenzyl or cyanomethyl. For the N-pentafluorobenzyl derivative, Coulombic interaction with the pyridinium moiety is complemented in the solid state by anion-π interactions with the perfluorophenyl ring. Bromide and chloride are bound by these cations in a 1:1 stoichiometry. Catalysis of the C-C coupling between 1-chloroisochroman (and related electrophiles) with silyl ketene acetals occurs at -78 °C and at low catalyst loading (2 mol %).
- Berkessel, Albrecht,Das, Somnath,Pekel, Daniel,Neud?rfl, J?rg-M.
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supporting information
p. 11660 - 11664
(2016/02/18)
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- Synthesis of sulfonylhydrazone- and acylhydrazone-substituted 8-ethoxy-3-nitro-2h-chromenes as potent antiproliferative and apoptosis inducing agents
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3-Nitro-2H-chromenes have recently been identified as a novel class of potent antitumor agents. In view of the favorable effects shown by sulfonylhydrazones and acylhydrazones, we designed and synthesized a series of sulfonylhydrazone- and acylhydrazone-substituted 8-ethoxy-3-nitro-2H-chromene derivatives, and evaluated their cell growth inhibition activities against A549, KG-1, A2780, and K562 cells. All the tested compounds exhibited more potent antiproliferative activity than BENC-511 against KG-1 cells. These compounds displayed IC50 values in the nanomolar range against A2780 cells. Compound 7d showed prominent cytotoxicity against K562 cells with an IC 50 of 0.11 μM, which was comparable to that of BENC-511. Compound 7d arrested K562 cells at the G1 phase at high concentrations and induced apoptosis in K562 cells. Furthermore, 7d increased the levels of cleaved caspase-3, decreased the expression of bcl-2 and induced the cleavage of poly(ADP-ribose) polymerase in K562 cells. Thus, this study provides the development of a series of novel compounds as effective antitumor agents with apoptotic death ability.
- Zhang, Datong,Ma, Yuntong,Liu, Yu,Liu, Zhao-Peng
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p. 576 - 588
(2014/08/18)
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- Diaryl-Substituted Azolylthioacetamides: Inhibitor Discovery of New Delhi Metallo-β-Lactamase-1 (NDM-1)
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The emergence and spread of antibiotic-resistant pathogens is a global public health problem. Metallo-β-lactamases (MβLs) such as New Delhi MβL-1 (NDM-1) are principle contributors to the emergence of resistance because of their ability to hydrolyze almost all known β-lactam antibiotics including penicillins, cephalosporins, and carbapenems. A clinical inhibitor of MBLs has not yet been found. In this study we developed eighteen new diaryl-substituted azolylthioacetamides and found all of them to be inhibitors of the MβL L1 from Stenotrophomonas maltophilia (KiiiII ion(s) preferentially via the triazole moiety, while other moieties interact mostly with the conserved active site residues Lys224 (CcrA, NDM-1, and ImiS) or Ser221 (L1).
- Zhang, Yi-Lin,Yang, Ke-Wu,Zhou, Ya-Jun,LaCuran, Alecander E.,Oelschlaeger, Peter,Crowder, Michael W.
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supporting information
p. 2445 - 2448
(2015/08/24)
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- A catalyst-free protocol for direct oxidative esterification of alcohols and aldehydes
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A fast, simple, and efficient protocol for the direct conversion of alcohols and aldehydes to methyl ester has been developed using TsNBr2without any catalyst. The one pot reaction proceeds in the presence of a base at room temperature in methanol, to produce the corresponding methyl ester in high yield within a short time.
- Rajbongshi, Kamal Krishna,Sarma, Manas Jyoti,Phukan, Prodeep
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p. 5358 - 5360
(2015/01/08)
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- NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles
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The pair NaBH4-TMEDA as hydride source and a palladium catalyst in THF prove to be an efficient system for the hydrodehalogenation of halogenated heterocycles with one or more heteroatoms. In general, Pd(OAc) 2-PPh3 rapidly hydrodehalogenates reactive halo-heterocycles such as bromo-pyridines, -quinolines, -thiophenes, -indoles, -imidazoles, etc., at room temperature in very good yields, whereas in most cases PdCl2(dppf) reduces less reactive halides such as chloro-pyridines, -quinolines, -pyrimidines and bromo-indoles, -benzofurans, etc. Moreover, PdCl2(tbpf) shows to be even more active removing the 2- and 5-chlorine from both thiophene and thiazole rings. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene and nitrile substituents. Moreover, with a proper selection of the catalyst it is also possible to obtain a good control in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.
- Chelucci, Giorgio,Figus, Susanna
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p. 191 - 209
(2014/07/21)
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- Methyl salicylate as a selective methylation agent for the esterification of carboxylic acids
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Methyl salicylate is a selective and inexpensive methylating agent for the esterification of carboxylic acids with a wide range of functional group tolerance. The intramolecular hydrogen bonds between the carboxylate and hydroxyl groups in methyl salicylate are essential for the transformation. Allyl, benzyl, methallyl, and propargyl salicylates can also be used as alkylating agents for the preparation of the corresponding alkyl carboxylates.
- Chen, Si,Jia, Lei,Li, Xiaonan,Luo, Meiming
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p. 263 - 268
(2014/03/21)
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- Synthesis, spectroscopic and radical scavenging studies of palladium(II)-hydrazide complexes
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In present study, a series of palladium(II) complexes with biologically active hydrazide ligands have been synthesized, characterized and screened for their antioxidant (superoxide and DPPH radical scavenging) properties. Spectral studies (FT-IR, EI-mass, 13C and 1H NMR spectroscopy) and physico-chemical measurements including elemental analysis, magnetic susceptibility and conductivity measurements represented square planar structure for all complexes. Substituted and unsubstituted benzohydrazides (1-4) have shown monodentate behavior forming complexes of general formula [PdL 2Cl2]. However, pyridine-carbohydrazides (5 and 6) were coordinated in bidentate fashion of [PdLCl2] general formula producing stable five-membered chelate ring. All palladium complexes were found to be considerably more potent inhibitors of DPPH free radical compared to free hydrazides. These complexes are even stronger DPPH scavengers than standard antioxidant propyl gallate. The complexes have also shown good superoxide scavenging ability compared to inactive free hydrazides, however complexes are weaker superoxide scavengers than ascorbic acid, a standard superoxide inhibitor. An interesting structure activity relationship has been evaluated.
- Ain, Qurrat Ul,Ashiq, Uzma,Jamal, Rifat Ara,Mahrooof-Tahir, Mohammad
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p. 683 - 689
(2013/11/06)
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- NHC-catalysed aerobic aldehyde-esterifications with alcohols: No additives or cocatalysts required
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A highly efficient, broad scope, additive-free mild protocol for the oxidative carbene-catalysed esterification of aldehydes (including the related aqueous oxidation to acids) has been developed.
- Delany, Eoghan G.,Fagan, Claire-Louise,Gundala, Sivaji,Mari, Alessandra,Broja, Thomas,Zeitler, Kirsten,Connon, Stephen J.
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supporting information
p. 6510 - 6512
(2013/07/26)
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- NHC-catalysed highly selective aerobic oxidation of nonactivated aldehydes
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This publication describes a highly selective oxidation of aldehydes to the corresponding acids or esters. The reaction proceeds under metal-free conditions by using N-heterocyclic carbenes as organocatalysts in combination with environmentally friendly oxygen as the terminal oxidation agent.
- Moehlmann, Lennart,Ludwig, Stefan,Blechert, Siegfried
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p. 602 - 607
(2013/04/24)
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- N-Heterocyclic carbene catalyzed esterification of aromatic aldehydes with alcohols under aerobic conditions
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A simple, organocatalytic procedure for the direct oxidative esterification of a variety of aromatic aldehydes with alcohols has been described that affords the corresponding aromatic esters in high yields. The method employs N-heterocyclic carbenes as catalysts and molecular O2 as an oxidant under ambient conditions.
- Kiran, I. N. Chaithanya,Lalwani, Komal,Sudalai, Arumugam
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p. 1695 - 1698
(2013/03/13)
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- Acylated dolabellane-type diterpenes from Nigella sativa seeds with triglyceride metabolism-promoting activity in high glucose-pretreated HepG2 cells
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Two new acylated dolabellane-type diterpenes, nigellamines B3 (9) and D (10), were isolated from Nigella sativa (Ranunculaceae) seeds using column chromatography and preparative HPLC. Their structures were determined based on chemical and physi
- Morikawa, Toshio,Ninomiya, Kiyofumi,Xu, Fengming,Okumura, Naomichi,Matsuda, Hisashi,Muraoka, Osamu,Hayakawa, Takao,Yoshikawa, Masayuki
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p. 198 - 204
(2013/08/25)
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- Selective oxidation of alcohols to esters using heterogeneous Co 3O4-N@C catalysts under mild conditions
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Novel cobalt-based heterogeneous catalysts have been developed for the direct oxidative esterification of alcohols using molecular oxygen as benign oxidant. Pyrolysis of nitrogen-ligated cobalt(II) acetate supported on commercial carbon transforms typical homogeneous complexes to highly active and selective heterogeneous Co3O4-N@C materials. By applying these catalysts in the presence of oxygen, the cross and self-esterification of alcohols to esters proceeds in good to excellent yields.
- Jagadeesh, Rajenahally V.,Junge, Henrik,Pohl, Marga-Martina,Radnik, Joerg,Brueckner, Angelika,Beller, Matthias
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supporting information
p. 10776 - 10782
(2013/08/23)
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- Discovery of new orally effective analgesic and anti-inflammatory hybrid furoxanyl N-acylhydrazone derivatives
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We report the design, the synthesis and the biological evaluation of the analgesic and anti-inflammatory activities of furoxanyl N-acylhydrazones (furoxanyl-NAH) by applying molecular hybridization approach. Hybrid compounds with IL-8-release inhibition capabilities were identified. Among them, furoxanyl-NAH, 17, and benzofuroxanyl-derivative, 24, together with furoxanyl-NAH derivative, 31, without IL-8 inhibition displayed both orally analgesic and anti-inflammatory activities. These hybrid derivatives do not have additional LOX- or COX-inhibition activities. For instance, LOX-inhibition by furoxanyl-NAH derivative, 42, emerged as a structural lead to develop new inhibitors. The lack of mutagenicity of the active derivatives 17, 31, and 42, allow us to propose them as candidates for further clinical studies. These results confirmed the success in the exploitation of hybridization strategy for identification of novel N-acylhydrazones (NAH) with optimized activities.
- Hernández, Paola,Cabrera, Mauricio,Lavaggi, María Laura,Celano, Laura,Tiscornia, Inés,Rodrigues Da Costa, Thiago,Thomson, Leonor,Bollati-Fogolín, Mariela,Miranda, Ana Luisa P.,Lima, Lidia M.,Barreiro, Eliezer J.,González, Mercedes,Cerecetto, Hugo
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experimental part
p. 2158 - 2171
(2012/05/04)
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- Calix[4]arene based 1,3,4-oxadiazole and thiadiazole derivatives: Design, synthesis, and biological evaluation
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In the present investigation, we describe some novel calixarene based heterocyclic compounds (5a-5i) in which 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives have been coupled with 5,11,17,23-tetra-tert-butyl-25,27- bis(chlorocarbonyl-methoxy)-26,28-dihydroxy calix[4]arene. All the newly synthesized calixarene based heterocyclic compounds have been characterized by elemental analysis and various spectroscopic methods like FTIR, 1H NMR, 13C NMR, and FAB-MS. All the final scaffolds have been subjected to antioxidant activity, in vitro antimicrobial screening against two gram (+ve) bacteria (S. aureus, S. pyogenes), two gram (-ve) bacteria (E. coli, P. aeruginosa) and two fungal strains (C. albicans, A. clavatus) and also have been screened for their antitubercular activity against Mycobacterium tuberculosis H37Rv.
- Patel, Manishkumar B.,Modi, Nishith R.,Raval, Jignesh P.,Menon, Shobhana K.
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body text
p. 1785 - 1794
(2012/04/23)
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