- First asymmetric Abramov-type phosphonylation of aldehydes with trialkyl phosphites catalyzed by chiral Lewis bases
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Chiral phosphine oxides (Lewis bases) catalyze silicon tetrachloride-mediated, enantioselective phosphonylation of aldehydes with trialkyl phosphites (Abramov-type reaction), which leads to optically active α-hydroxyphosphonates with moderate enantioselec
- Nakanishi, Kyoko,Kotani, Shunsuke,Sugiura, Masaharu,Nakajima, Makoto
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- Stereoselective Aldol Reactions via Enolates of α-Acylphosphonate Diesters
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In the reaction between the lithium enolate (2) of diethyl propionylphosphonate (1) and benzaldehyde, the syn-product (3s) is formed with high diastereoselectivity, as a result of structural rigidity caused by Li+ interactions with the phosphoryl oxygen.
- Longmire, Cynthia F.,Evans, Slayton A.
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- 1,1,2-Triphenyl-1,2-ethanediol: A host for carboxylic acids and amides in coordinatoclathrates
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The chiral diols (R)- and (S)-1 are found to form inclusion compounds with carboxylic acids and amides, as indicated by the relevant IR spectra. Two clathrates, (R)-1 · CH3CO2H and (S)-1 · CH3NHCHO have been characterized
- Ridder, Daniel,Wunderlich, Hartmut,Braun, Manfred
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- Crystal structure, vibrational, spectral investigation, quantum chemical DFT calculations and thermal behavior of Diethyl [hydroxy (phenyl) methyl] phosphonate
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Single Diethyl [hydroxy (phenyl) methyl] phosphonate (DHPMP) crystal with chemical formula C11H17O4P, was synthesized via the base-catalyzed Pudovik reaction and Lewis acid as catalyst. The results of SXRD analyzes indicate that this compound crystallizes into a mono-clinic system with space group P21/n symmetry and Z = 4. The crystal structure parameters are a = 9.293 ?, b = 8.103 ?, c = 17.542 ?, β = 95.329° and V = 1315.2 ?3, the structure displays one inter-molecular O—H?O hydrogen bonding. The UV–Visible absorption spectrum shows that the crystal exhibits a good optical transmission in the visible domain, and strong absorption in middle ultraviolet one. The vibrational frequencies of various functional groups present in DHPMP crystal have been deduced from FT-IR and FT-Raman spectra and then compared with theoretical values performed with DFT (B3LYP) method using 6-31G (p, d) basis sets. Chemical and thermodynamic parameters such as: ionization potential (I), electron affinity (A), hardness (σ), softness (η), electronegativity (χ) and electrophilicity index (ω), are also calculated using the same theoretical method. The thermal decomposition behavior of DHPMP, studied by using thermogravimetric analysis (TDG), shows a thermal stability until to 125 °C.
- Ouksel, Louiza,Chafaa, Salah,Bourzami, Riadh,Hamdouni, Noudjoud,Sebais, Miloud,Chafai, Nadjib
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- A study on the Kabachnik-Fields reaction of benzaldehyde, propylamine, and diethyl phosphite by in situ Fourier transform IR spectroscopy
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The phospha-Mannich condensation of benzaldehyde, n-propylamine, and diethyl phosphite carried out at 80°C in acetonitrile takes place via the imine (PhC=N-Pr) intermediate as suggested by in situ FT-IR spectroscopy. Copyright
- Keglevich, Gyoergy,Fehervari, Andras,Csontos, Istvan
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- Tetrafluorine-containing ketones and acetoacetates: Synthesis and mechanistic study
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Addition of trimethylsilyl trifluoroacetate to the carbanions of α-fluorobenzyl-phosphonate (3) or diisopropyl(fluorocarbethoxymethyl) phosphonate (9) formed the corresponding intermediates [CF3C(O)CFPh] -Li+ (10) and [CF3C(O)CFCO2Et] -Li+ (11), respectively. Subsequent protonation, alkylation or allylation of 10 and 11 afforded trifluoromethyl fluorobenzyl ketones 12 and ethyl 2,4,4,4-tetra-fluoroacetoacetates 13. Based on the results obtained, a plausible mechanism was proposed.
- Tsai, Hou-Jen,Hsieh, Chi-Wei
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- Efficient synthesis of ether phosphonates using trichloroacetimidate and acetate coupling methods
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A series of ether phosphonates have been prepared by trichloroacetimidate and acetate coupling methods. Trichloroacetimidates or acetates were treated with primary and secondary alcohols as O-nucleophiles in the presence of catalytic TMSOTf to afford 21 examples of diethyl alkyloxy(substitutedphenyl)methyl phosphonates via C-O bond formation in 55-90% yields and short reaction time.
- Fathalla, Walid,Ali, Ibrahim A. I.,Pazdera, Pavel
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- An efficient and simple strategy toward the synthesis of highly functionalized compounds
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The expedient syntheses of small libraries of ((β-ethoxycarbonyl, -cyano and -acetyl)propyloxy) methylphosphonate scaffolds bearing olefin, sulfanyl, or amine functions are described. All these new derivatives are readily produced from easily available starting reagents (aldehydes, electron-poor olefins, and dialkylphosphites) following a three steps reaction sequence of condensations, SN2′-type reaction and a conjugated thia- or aza-Michael 1,4-addition with aromatic and aliphatic thiol or amine nucleophiles.
- Jmai, Momtez,Efrit, Mohamed Lotfi,Dubreuil, Didier,Blot, Virginie,Lebreton, Jacques,M'rabet, Hédi
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p. 978 - 995
(2021/08/06)
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- Synthesis of novel α-hydroxyphosphonates along with α-aminophosphonates as intermediates
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New phosphoryl α-hydroxyphosphonates, their acylated derivatives, as well as α-aminophosphonates were synthesized as potentionally biologycally active substrates. The reverzible formation of α-hydroxyphosphonates allowing a few interesting side-reactions was also observed.
- Belovics, Alexandra,H?gele, Gerhard,Keglevich, Gy?rgy,Varga, Petra R.
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- Method for synthesizing aromatic ring-containing alpha-hydroxyphosphonate through copper catalysis
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The invention relates to a method for synthesizing aromatic ring-containing alpha-hydroxyphosphonate through copper catalysis. The method comprises the following steps: dissolving diethyl phosphite and aromatic aldehyde in an organic solvent, adding a cop
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Paragraph 0024-0026
(2020/05/01)
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- Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes
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We synthesized substituted benzaldehyde derived α-hydroxyphosphonates (αOHP), α-hydroxyphosphonic acids (αOHPA) and α-phosphinoyloxyphosphonates (αOPP) and characterized their cytotoxicity against a panel of cancer cell lines. A library containing 56 analogues was screened against Mes-Sa parental and Mes-Sa/Dx5 multidrug resistant uterine sarcoma cell lines, using a fluorescence-based cytotoxicity assay. The cytotoxicity screening revealed that dibenzyl-αOHPs and dimethyl-α-diphenyl-OPPs were the most active clusters, which encouraged us to synthesize further dibenzyl-α-diphenyl-OPP derivatives that elicited pronounced cell killing. Further structure-activity relationships showed the relevance of hydrophobicity and the position of substituents on the main benzene ring as determinants of toxicity. The most active analogs proved to be equally, or even more toxic to the multidrug resistant (MDR) cell line Mes-Sa/Dx5, suggesting these compounds may overcome P-glycoprotein mediated multidrug resistance by evading the drug transporter.
- Rádai, Zita,Windt, Tímea,Nagy, Veronika,Füredi, András,Kiss, Nóra Zsuzsa,Ranelovi?, Ivan,Tóvári, József,Keglevich, Gy?rgy,Szakács, Gergely,Tóth, Szilárd
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supporting information
p. 14028 - 14035
(2019/09/18)
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- Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation
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A promiscuous lipase-catalyzed carbon-phosphorus bond formation is presented. The developed enzymatic Pudovik-Abramov reaction of various aromatic and aliphatic aldehydes with dialkyl phosphonates provides biologically and pharmacologically relevant α-hyd
- Koszelewski, Dominik,Ostaszewski, Ryszard
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p. 2554 - 2558
(2019/04/30)
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- Rational synthesis of α-hydroxyphosphonic derivatives including dronic acids
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New, green methods have been elaborated for the syntheses of α-hydroxyphosphonates and α-hydroxymethylenebisphosphonic derivatives (HMBPs, dronates). α-Hydroxyphosphonates were prepared via the Pudovik reaction, while the synthesis of HMBPs has been performed in the three-component reaction of carboxylic acids, phosphorus trichloride and phosphorus acid.
- Grün, Alajos,Rádai, Zita,S?regi-Nagy, Dávid Illés,Greiner, István,Keglevich, Gy?rgy
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p. 386 - 387
(2019/01/18)
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- CeCl3?7H2O-catalysed hydrophosphonylation of aldehydes and ketones: An expeditious route to α-hydroxyphosphonates under solvent-free conditions
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A cerium(III) chloride-catalysed expeditious synthesis of α-hydroxyphosphonates via a modified Abramov synthetic protocol has been developed. The scope of the current protocol is broad, with a range of aromatic, α,β-unsaturated and heterocyclic aldehydes
- Mahesh,Sharma, Rupali,Kour, Parteek,Kumar, Anil
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p. 1091 - 1097
(2019/07/04)
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- Hydrophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes
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This work reports the first method for the synthesis of α-hydroxyphosphonates from aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes. The best results were obtained using the system HP(O)(OEt)2/[RuClCp(PPh3)2
- Cabrita, Ivania R.,Florindo, Pedro R.,Costa, Paulo J.,Oliveira, M. Concei??o,Fernandes, Ana C.
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- Synthesis, spectroscopic characterization, and in vitro antibacterial evaluation of novel functionalized sulfamidocarbonyloxyphosphonates
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Several new sulfamidocarbonyloxyphosphonates were prepared in two steps, namely carbamoylation and sulfamoylation, by using chlorosulfonyl isocyanate (CSI), α-hydroxyphosphonates, and various amino derivatives and related (primary or secondary amines, β-amino esters, and oxazolidin-2-ones). All structures were confirmed by 1H, 13C, and 31P NMR spectroscopy, IR spectroscopy, and mass spectroscopy, as well as elemental analysis. Eight compounds were evaluated for their in vitro antibacterial activity against four reference bacteria including Gram-positive Staphylococcus aureus (ATCC 25923), and Gram-negative Escherichia coli (ATCC 25922), Klebsiella pneumonia (ATCC 700603), Pseudomonas aeruginosa (ATCC 27853), in addition to three clinical strains of each studied bacterial species. Compounds 1a–7a and 1b showed significant antibacterial activity compared to sulfamethoxazole/trimethoprim, the reference drug used in this study.
- Bouzina, Abdeslem,Bechlem, Khaoula,Berredjem, Hajira,Belhani, Billel,Becheker, Imène,Lebreton, Jacques,Le Borgne, Marc,Bouaziz, Zouhair,Marminon, Christelle,Berredjem, Malika
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supporting information
p. 1 - 14
(2018/07/31)
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- Highly efficient green synthesis of α-hydroxyphosphonates using a recyclable choline hydroxide catalyst
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Choline hydroxide has been found to be an efficient basic ionic liquid catalyst for the synthesis of α-hydroxyphosphonates. Hydrophosphonylation of aldehydes was performed via the nucleophilic addition of diethylphosphite to aldehydic carbonyl compounds, in the presence of choline hydroxide under neat as well as solvent conditions. A wide array of substrates, including aromatic, fused aromatic, and heterocyclic aldehydes, were efficiently converted to their corresponding products in good yields. This protocol provides an alternative method for the straightforward synthesis of α-hydroxyphosphonates in high yields.
- Kalla, Reddi Mohan Naidu,Zhang, Yu,Kim, Il
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p. 5373 - 5379
(2017/07/11)
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- Benzyl Mono-P-Fluorophosphonate and Benzyl Penta-P-Fluorophosphate Anions Are Physiologically Stable Phosphotyrosine Mimetics and Inhibitors of Protein Tyrosine Phosphatases
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α,α-Difluoro-benzyl phosphonates are currently the most popular class of phosphotyrosine mimetics. Structurally derived from the natural substrate phosphotyrosine, they constitute classical bioisosteres and have enabled the development of potent inhibitors of protein tyrosine phosphatases (PTP) and phosphotyrosine recognition sites such as SH2 domains. Being dianions bearing two negative charges, phosphonates, however, do not permeate membranes and thus are often inactive in cells and have not been a successful starting point toward therapeutics, yet. In this work, benzyl phosphonates were modified by replacing phosphorus-bound oxygen atoms with phosphorus-bound fluorine atoms. Surprisingly, mono-P-fluorophosphonates were fully stable under physiological conditions, thus enabling the investigation of their mode of action toward PTP. Three alternative scenarios were tested and mono-P-fluorophosphonates were identified as stable reversible PTP1B inhibitors, despite of the loss of one negative charge and the replacement of one oxygen atom as an H-bond donor by fluorine. In extending this replacement strategy, α,α-difluorobenzyl penta-P-fluorophosphates were synthesized and found to be novel phosphotyrosine mimetics with improved affinity to the phosphotyrosine binding site of PTP1B.
- Wagner, Stefan,Accorsi, Matteo,Rademann, J?rg
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supporting information
p. 15387 - 15395
(2017/11/09)
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- Bi(NO3)3.5H2O catalyzed phosphonylation of aldehydes: An efficient route to α-hydroxyphosphonates
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The Bi(NO3)3.5H2O mediated synthesis of α-hydroxyphosphonates via phosphonylation of aldehydes is reported herein. Both conventional and microwave technology was efficiently applied to range of aromatic, heteroaromatic, α,
- Kumar, Anil,Jamwal, Shivali,Khan, Shahaba,Singh, Nasseb,Rai, Vijai K.
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p. 381 - 385
(2017/02/18)
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- Synthesis and herbicidal activity of α-[(substituted phenoxybutyryloxy or valeryoxy)]alkylphosphonates and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine
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Based on our previous work on the structural modification of the lead compound I, three series of novel fluorine-containing phosphonates derivatives (II, III and IV) were designed and synthesized. Their post-emergence herbicidal activities against some species of weeds were evaluated in a green house. The compounds II were synthesized by introducing of two methylene into the structure I. Compared with the commercial herbicidal clacyfos, compounds II showed moderate herbicidal activity with 60–85% inhibition effect against chingma abutilon (Abutilon theophrasti), common amaranth (Amaranthus retroflexus) and white eclipta (Eclipta prostrate) at a rate of 150 g ai/ha. The compounds III were designed by introducing open-chain phosphonates, which displayed notable herbicidal activity. Especially, the compounds III-1–III-4, III-6, III-8, III-11 and III-12 exhibited significant herbicidal activity (80–100%) comparing to the clacyfos against all tested broadleaf weeds, while compounds IV with five carbon atoms in the carboxylic acid chain were inactive against all of the tested weeds. Structure-activity relationship analyses indicated that the length of the carbon chain had a great effect on the herbicidal activity. Furthermore, a broad spectrum test confirmed that compounds III-4 and III-8 were comparable with glyphosate against all of the tested weeds at a rate of 75 g ai/ha.
- Wang, Wei,Zhou, Yuan,Peng, Hao,He, Hong-Wu,Lu, Xing-Tao
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- Phosphono-replaced methyl alcohol derivative, and preparation method and application thereof
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The invention discloses a phosphono-replaced methyl alcohol derivative, and a preparation method and application thereof. The phosphono-replaced methyl alcohol derivative has the advantages that a (hetero) aryl methyl alcohol derivate serves as an initiator, and raw materials are easy to get and have great varieties; products obtained according to the preparation method have various types and wide application ranges, and serve as ligands which coordinate with rhodium to obtain various aldehydes through catalyzed synthesis; the phosphono-replaced (hetero) aryl methyl alcohol can be transformed into phosphonic compounds conveniently; the phosphonic compounds serving as photoinitiators can be widely applied to production of high polymer materials, paint, binders, adhesive tapes and the like. The preparation method has the advantages that reactions are achieved in the air, reaction conditions are mild, yield of target products is high, pollution is small, reaction operations and post-treatment processes are simple, and the preparation method is suitable for industrial production.
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Paragraph 0017
(2017/08/28)
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- A kind of rare earth metal arylamine compound and its preparation method and application
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The invention discloses a rare-earth metal arylamine group compound as well as preparation method and application thereof. The invention discloses the rare-earth metal arylamine group compound which is characterized in that a general formula of the rare-e
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Paragraph 0053-0054
(2017/01/17)
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- A simple heterogeneous catalyst for phosphite addition on carbonyl groups
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A cheap and easily recoverable heterogeneous catalyst could efficiently trigger C-P bond formation by selective addition of phosphites to the carbonyl group of aldehydes and ketones. The reactions afford the desired products in good to excellent yields an
- Santacroce, Veronica,Paris, Emanuele,Cauzzi, Daniele,Maggi, Raimondo,Maestri, Giovanni
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supporting information
p. 463 - 466
(2016/02/18)
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- Syntheses of bimetallic rare-earth bis(cyclopentadienyl) derivatives supported by bridged bis(guanidinate) ligands and their catalytic property for the hydrophosphonylation of aldehydes
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Some bimetallic rare earth bis(cyclopentadienyl) derivatives supported by bridged bis(guanidinate) ligands {(C5H5)2RE[(RN)2CN(CH2)2]}2 [R = iPr, RE = Yb(1), Er(2), Y(3
- Nie, Kun,Liu, Chengwei,Zhang, Yong,Yao, Yingming
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- Cholic acid-alpha-amino phosphonate derivative and synthesis method thereof
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The invention belongs to the field of medicine chemistry and particularly relates to a cholic acid-alpha-amino phosphonate derivative and a preparation method thereof.Cholic acid and phosphate ester serve as raw materials, and the cholic acid-alpha-amino
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Paragraph 0015; 0016; 0026; 0030
(2016/10/09)
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- Bile acid-alpha-hydroxyphosphonate derivatives and synthetic method thereof
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The invention belongs to the field of pharmaceutical chemistry and particularly relates to novel bile acid-alpha-hydroxyphosphonate compounds and a preparation method thereof. Bile acid and phosphate ester are taken as raw materials, the bile acid-alpha-h
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Paragraph 0017; 0018; 0020; 0021
(2016/12/22)
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- Isoprenoid Biosynthesis Inhibitors Targeting Bacterial Cell Growth
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We synthesized potential inhibitors of farnesyl diphosphate synthase (FPPS), undecaprenyl diphosphate synthase (UPPS), or undecaprenyl diphosphate phosphatase (UPPP), and tested them in bacterial cell growth and enzyme inhibition assays. The most active compounds were found to be bisphosphonates with electron-withdrawing aryl-alkyl side chains which inhibited the growth of Gram-negative bacteria (Acinetobacter baumannii, Klebsiella pneumoniae, Escherichia coli, and Pseudomonas aeruginosa) at ~1–4 μg mL?1levels. They were found to be potent inhibitors of FPPS; cell growth was partially “rescued” by the addition of farnesol or overexpression of FPPS, and there was synergistic activity with known isoprenoid biosynthesis pathway inhibitors. Lipophilic hydroxyalkyl phosphonic acids inhibited UPPS and UPPP at micromolar levels; they were active (~2–6 μg mL?1) against Gram-positive but not Gram-negative organisms, and again exhibited synergistic activity with cell wall biosynthesis inhibitors, but only indifferent effects with other inhibitors. The results are of interest because they describe novel inhibitors of FPPS, UPPS, and UPPP with cell growth inhibitory activities as low as ~1–2 μg mL?1.
- Desai, Janish,Wang, Yang,Wang, Ke,Malwal, Satish R.,Oldfield, Eric
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p. 2205 - 2215
(2016/10/22)
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- Synthesis and Herbicidal Activity of α-(Substituted Phenoxybutyryloxy or Valeryloxy)alkylphosphonates and 2-(Substituted Phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one
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On the basis of our work on the modification of alkylphosphonates 1, a series of α-(substituted phenoxybutyryloxy or valeryloxy)alkylphosphonates (4-5) and 2-(substituted phenoxybutyryloxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one (6) were designed and synthesized. The bioassay results indicated that 14 of title compounds 4 exhibited significant postemergence herbicidal activity against velvetleaf, common amaranth, and false daisy at 150 g ai/ha. Compounds 5 were inactive against all tested weeds. Compounds 6 exhibited moderate to good inhibitory effect against the tested dicotyledonous weeds. Structure-activity relationship (SAR) analyses showed that the length of the carbon chain as linking bridge had a great effect on the herbicidal activity. Broad-spectrum tests of compounds 4-1, 4-2, 4-9, 4-30, and 4-36 were carried out at 75 g ai/ha. Especially, 4-1 exhibited 100% inhibition activity against the tested dicotyledonous weeds, which was higher than that of glyphosate.
- Wang, Wei,Zhang, Sha-Sha,Zhou, Yuan,Peng, Hao,He, Hong-Wu,Lu, Xing-Tao
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p. 6911 - 6915
(2016/10/03)
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- Ultrasound assisted green synthesis of α-hydroxyphosphonates under solvent-free conditions
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Abstract: A simple, efficient and environmentally benign method for the synthesis of α-hydroxyphosphonates by reaction of an aldehyde or a ketone, and trialkylphosphite is effectively accomplished under ultrasound irradiation and solvent-free and catalyst
- Bouzina, Abdeslem,Aouf, Nour-eddine,Berredjem, Malika
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p. 5993 - 6002
(2016/06/01)
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- Synthesis and characterization of ytterbium guanidinates stabilized by bridged bis(phenolate) ligand and their application for the hydrophosphonylation reaction of aldehydes
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A series of ytterbium guanidinato complexes stabilized by an amine-bridged bis(phenolate) ligand were prepared, and their catalytic property for the hydrophosphonylation reaction of aldehydes was explored. Metathesis reactions of amine-bridged bis(phenola
- Zeng, Tinghua,Qian, Qinqin,Wang, Yaorong,Yao, Yingming,Shen, Qi
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- Syntheses of bimetallic lanthanide bis(amido) complexes stabilized by bridged bis(guanidinate) ligands and their catalytic activity toward the hydrophosphonylation reaction of aldehydes and ketones
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A series of bimetallic lanthanide bis(amido) complexes stabilized by bridged bis(guanidinate) ligands {[(Me3Si)2N]2Ln[(RN)2-CN(CH2)2]}2 [R= i Pr, Ln=Sm (1), Yb (2), Y
- Nie, Kun,Liu, Chengwei,Zhang, Yong,Yao, Yingming
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p. 1451 - 1460
(2015/09/02)
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- Amido rare-earth complexes supported by an ansa bis(amidinate) ligand with a rigid 1,8-naphthalene linker: Synthesis, structures and catalytic activity in rac-lactide polymerization and hydrophosphonylation of carbonyl compounds
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A synthetic approach to rare-earth amido complexes coordinated by an ansa bis(amidinate) ligand with a 1,8-naphthalene linker was developed and allowed for the synthesis of a series of complexes [1,8-C10H6{NC(tBu)N-2,6-Me2
- Yakovenko, Marina V.,Udilova, Natalia Yu.,Glukhova, Tatyana A.,Cherkasov, Anton V.,Fukin, Georgy K.,Trifonov, Alexander A.
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p. 1083 - 1093
(2015/02/19)
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- MgO-coated-Fe3O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of 1-hydroxyphosphonates
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Nanosize magnetic particles coated with magnesium oxide (core/shell nanoparticles) have been prepared and used for the synthesis of 1-hydroxyalkyl phosphonates. Catalytic activity studies show that the magnetic particles coated with magnesium oxide have h
- Kaboudin, Babak,Kazemi, Foad,Habibi, Fereshteh
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p. 469 - 475
(2015/02/05)
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- Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates
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The Kabachnik-Fields reaction of 4-piperidone hydrochloride monohydrate, an aromatic aldehyde and triethyl phosphite in the presence of triethylamine and magnesium perchlorate affords diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates in moderate yield
- Makarov, Mikhail V.,Skvortsov, Evgenii A.,Brel, Valery K.
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p. 232 - 233
(2015/06/17)
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- Pd-catalyzed carbonylative access to aroyl phosphonates from (hetero)aryl bromides
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The first transition-metal catalysed carbonylation with a phosphorus nucleophile is presented. This transformation provides efficient and mild access to aroylphosphonates under mild conditions, thus ensuring a broad substrate scope. The utility of aroylph
- Lian, Zhong,Yin, Hongfei,Friis, Stig D.,Skrydstrup, Troels
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supporting information
p. 7831 - 7834
(2015/05/13)
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- Synthesis, structure, and catalytic activity of novel trinuclear rare-earth metal amido complexes incorporating μ-η5:η1 bonding indolyl and μ3-oxo groups
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The reactions of different pyrrolyl-functionalized indoles with rare-earth metal(iii) amides [(Me3Si)2N]3RE III(μ-Cl)Li(THF)3 (RE = Yb, Er, Dy, Eu, Y) produced different kinds of rare-earth metal amid
- Yang, Song,Zhu, Xiancui,Zhou, Shuangliu,Wang, Shaowu,Feng, Zhijun,Wei, Yun,Miao, Hui,Guo, Liping,Wang, Fenhua,Zhang, Guangchao,Gu, Xiaoxia,Mu, Xiaolong
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supporting information
p. 2521 - 2533
(2014/02/14)
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- Lanthanide anilido complexes: Synthesis, characterization, and use as highly efficient catalysts for hydrophosphonylation of aldehydes and unactivated ketones
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Lanthanide anilido complexes stabilized by the 2,6-diisopropylanilido ligand have been synthesized and characterized, and their catalytic activity for hydrophosphonylation reaction was explored. A reaction of anhydrous LnCl 3 with 5 equivalents
- Liu, Chengwei,Qian, Qinqin,Nie, Kun,Wang, Yaorong,Shen, Qi,Yuan, Dan,Yao, Yingming
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p. 8355 - 8362
(2014/06/09)
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- N -BuLi as a highly efficient precatalyst for hydrophosphonylation of aldehydes and unactivated ketones
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It was found for the first time that organic alkali metal compounds serve as highly efficient precatalysts for the hydrophosphonylation reactions of aldehydes and unactivated ketones with dialkyl phosphite under mild conditions. For ketone substrates, a reversible reaction was observed, and the influence of catalyst loading and reaction temperature on the reaction equilibrium was studied in detail. Overall, the hydrophosphonylation reactions catalyzed by 0.1 mol % n-BuLi were completed within 5 min for a broad range of substrates and generated a series of α-hydroxy phosphonates in high yields.
- Liu, Chengwei,Zhang, Yu,Qian, Qinqin,Yuan, Dan,Yao, Yingming
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supporting information
p. 6172 - 6175
(2015/01/09)
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- Synthesis and characterization of amidate rare-earth metal amides and their catalytic activities toward hydrophosphonylation of aldehydes and unactivated ketones
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Two novel amidate rare-earth metal amides Ln[N(SiMe3)2](κ2-L1)2(THF) (L1 = C6H5C(O)NC6H3(iPr)2) (Ln = Yb (1), Y (2)) were p
- Zhao, Lu,Ding, Hao,Zhao, Bei,Lu, Chengrong,Yao, Yingming
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- Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid as a recyclable catalyst for the kabachnik-fields reaction of isatins, imines, and aldehydes under solvent-free conditions
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Magnetic-nanoparticle-supported phosphotungstic acid has been used to efficiently catalyze the hydrophosphonylation reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α-hydroxy and α-amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle was proposed.
- Nazish, Mohd,Saravanan,Khan, Noor-Ul H.,Kumari, Prathibha,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Bajaj, Hari C.
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p. 1753 - 1760
(2015/02/02)
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- Synthesis of α-oxycarbanilinophosphonates and their anticholinesterase activities: The most potent derivative is bound to the peripheral site of acetylcholinesterase
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A novel method has been developed for the synthesis of α-oxycarbanilino phosphonates through a reaction of α-hydroxyphosphonates with isocyanate under microwave irradiation. The synthesized compounds were evaluated for their acetylcholinesterase (AChE) inhibition potency through IC50determination. Molecular modelling studies suggest that the most potent inhibitor (compound 4h, IC50 = 6.36 μM) is bound to the peripheral site of AChE, which suggests that it decreases the catalytic activity not through binding to the active site but through blocking the entrance of the active site gorge. This puts forward the potential of compound 4h and its derivatives to be used in the design of dual inhibitors: inhibition of the catalytic activity of AChE and of amyloid β aggregation.
- Kaboudin, Babak,Emadi, Saeed,Faghihi, Mohammad Reza,Fallahi, Maryam,Sheikh-Hasani, Vahid
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p. 576 - 582
(2015/02/19)
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- A rapid, convenient, solventless green approach for the synthesis of α-hydroxyphosphonates by grinding
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An efficient and convenient approach to the condensation reaction of aromatic aldehydes and diethyl phosphite using Na2CO3 as catalyst with grinding at room temperature (without any solvent) is described. This method provides several
- Kong, Du-Lin,Liu, Ren-Die,Li, Guo-Zhu,Zhang, Peng-Wei,Wu, Ming-Shu
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p. 1246 - 1248
(2014/06/09)
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- Air-stable zirconocene bis(perfluorobutanesulfonate) as a highly efficient catalyst for synthesis of α-aminophosphonates via Kabachnik-Fields reaction under solvent-free condition
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Zirconocene bis(perfluorobutanesulfonate) [Cp2Zr(OSO 2C4F9)2·2H2O] was successfully synthesized by treatment of Cp2ZrCl2 with C4F9SO3Ag, and was found to have the nature of air-stability, water tolerance, high thermal stability and strong Lewis acidity. This complex showed high catalytic efficiency for the synthesis of α-aminophosphonates via Kabachnik-Fields reaction of aldehydes/ketones, amines and diethyl phosphite under mild and solvent-free conditions. Furthermore, it can be reused without loss of activity in a test of five cycles. Compared with our previously reported complex of Cp2Zr(OSO 2C8F17)2·3H 2O·THF, this complex showed better catalytic activity.
- Li, Ningbo,Wang, Xie,Qiu, Renhua,Xu, Xinhua,Chen, Jinyang,Zhang, Xiaohong,Chen, Sihai,Yin, Shuangfeng
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p. 184 - 187
(2013/11/19)
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- Synthesis and biological activities of O, O-dialkyl 1-((4,6- Dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates
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(Equation present) A series of new 1-((4,6-dichloropyrimidin-2-yl) carbamyloxy) alkylphosphonates were designed and synthesized. The structures of all the title compounds were confirmed by IR, 1H-NMR, 31P-NMR and elemental analysis. The results of the bioassay showed that all of title compounds exhibited weak herbicidal activities against monocotyledons and dicotyledons; however, some of them showed potential plant growth regulatory activities. 2014 Copyright Taylor & Francis Group, LLC.
- Xu, Liang,You, Geyun,Peng, Hao,He, Hongwu
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p. 812 - 818
(2014/07/08)
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- Enantioselective acylphosphonylation-dual lewis acid-lewis base activation of aldehyde and acylphosphonate
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Acetoxyphosphonates were obtained by a one-step procedure consisting of reaction of diethyl acetylphosphonate with prochiral aldehydes in the presence of a catalytic system comprising a chiral Lewis acid, an achiral Lewis base, and a Br?nstedt base. Best
- Wen, Ye-Qian,Hertzberg, Robin,Moberg, Christina
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p. 6172 - 6178
(2014/07/21)
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- Applications of caged-designed proton sponges in base-catalyzed transformations Dedicated to Professor Milan Kratochvíl for his 90th birthday anniversary.
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Superbasic properties of caged proton sponges (PSs) - substituted diazatetracyclo[4.4.0.13,10.15,8]dodecanes (DTDs) - were utilized in Knoevenagel and Claisen-Schmidt condensations, the Pudovik reaction, and Michael addition. This investigation covers the influence of the solvent, reaction temperature, catalyst loadings as well as the electronic properties of substituents upon the reaction. Moreover, we provided an activity comparison between our new base and a well-known and commercially available proton sponge (DMAN). The basicity (in MeCN) of our chosen DTD (pKBH+=21.7±0.1) exceeded the prototypal PS - 1,8-bis(dimethylamino)naphthalene (DMAN, pKBH+=18.6), by three orders of magnitude. We proved that DTDs are reasonably active species in monitored reactions, which is a consequence of a hydrogen bridge angle (~130°) between the two nitrogen atoms and the captured proton. We present here syntheses of aminoindolizine, substituted 4H-chromene, and flavanones, and the unexpected formation of a bis-addition product formed after Michael addition, all under mild conditions.
- Galeta, Juraj,Potá?ek, Milan
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- Phospha-Michael Addition to in Situ Prepared 5-Arylmethylidene Meldrum's Acids
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Knoevenagel condensation reaction of an aldehyde and Meldrum's acid produces a 5-arylmethylidene Meldrum's acid, which undergoes Michael addition of a trialkyl phosphite under solvent-free conditions to afford the title compounds in good yields.
- Adib, Mehdi,Sheikhi, Ehsan,Rezaei, Narjes,Bijanzadeh, Hamid Reza,Mirzaei, Peiman
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p. 1331 - 1334
(2014/06/10)
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- E-Factor minimized hydrophosphonylation of aldehydes catalyzed by polystyryl-BEMP under solvent-free conditions
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An efficient protocol for the hydrophosphonylation of aromatic and aliphatic aldehydes catalyzed by PS-BEMP under solvent-free conditions (SolFC) has been reported. Addition reactions were performed by using equimolar amounts of reagents and the resulting
- Angelini, Tommaso,Bonollo, Simona,Lanari, Daniela,Pizzo, Ferdinando,Vaccaro, Luigi
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supporting information
p. 5042 - 5046
(2013/08/23)
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- Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst
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An extremely simple, high yielding, highly rapid and solvent-free protocol has been described for hydrophosphylation of aldehydes using potassium phosphate as catalyst. Easy commercial availability of the reusable catalyst, operational simplicity at ambie
- Kulkarni, Makarand A.,Lad, Uday P.,Desai, Uday V.,Mitragotri, Satish D.,Wadgaonkar, Prakash P.
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p. 148 - 152
(2013/04/24)
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- Rare-earth metal amido complexes supported by bridged bis(β- diketiminato) ligand as efficient catalysts for hydrophosphonylation of aldehydes and ketones
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A series of rare-earth metal amides supported by a cyclohexyl-linked bis(β-diketiminato) ligand were synthesized, and their catalytic activities for hydrophosphonylation of aldehydes and ketones were developed. Reaction of [(Me3Si)2N
- Miao, Hui,Zhou, Shuang Liu,Wang, Shao Wu,Zhang, Li Jun,Wei, Yun,Yang, Song,Wang, Fen Hua,Chen, Zheng,Chen, Yue,Yuan, Qing Bing
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p. 329 - 336
(2013/07/26)
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- Synthesis of α-oxycarbanilinophosphonates and their anticholinesterase activities: the most potent derivative is bound to the peripheral site of acetylcholinesterase
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A novel method has been developed for the synthesis of α- oxycarbanilino phosphonates through a reaction of α-hydroxyphosphonates with isocyanate under microwave irradiation. The synthesized compounds were evaluated for their acetylcholinesterase (AChE) inhibition potency through IC50determination. Molecular modelling studies suggest that the most potent inhibitor (compound 4h, IC50 = 6.36 M) is bound to the peripheral site of AChE, which suggests that it decreases the catalytic activity not through binding to the active site but through blocking the entrance of the active site gorge. This puts forward the potential of compound 4h and its derivatives to be used in the design of dual inhibitors: inhibition of the catalytic activity of AChE and of amyloid β aggregation.
- Kaboudin, Babak,Emadi, Saeed,Faghihi, Mohammad Reza,Fallahi, Maryam,Sheikh-Hasani, Vahid
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p. 576 - 582
(2013/05/08)
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- Lanthanide borohydrido complexes supported by ansa-bis(amidinato) ligands with a rigid o-phenylene linker: Effect of ligand tailoring on catalytic lactide polymerization
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A series of lanthanide monoborohydrido complexes {C6H 4-1,2-[NC(R)NR′]2}Ln(BH4)(L)n (Ln = Y, Nd, Sm; R = tBu, Ph; R′ = 2,6-Me2C6H 3, SiMe3; L = dme = dimeth
- Tolpygin, Aleksei O.,Skvortsov, Grigorii G.,Cherkasov, Anton V.,Fukin, Georgy K.,Glukhova, Tatyana A.,Trifonov, Alexander A.
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p. 6009 - 6018
(2014/01/06)
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- N-heterocyclic carbenes catalyzed phospho-aldol reaction of aldehydes
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An efficient phospho-aldol reaction of aldehydes catalyzed by N-heterocyclic carbenes (NHCs) has been developed. With 10 mol% stable NHC 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, various aldehydes reacted with dialkylphosphites smoothly to provide α-hydroxy phosphonates in 59% -99% yield. In this process, NHC was assumed to function as a carbon-centered bronsted base. Copyright
- He, Lin,Cai, Zhihua,Ma, Xiaowei,Du, Guangfen
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p. 1573 - 1576
(2014/01/06)
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- A catalyst-free, three-component decarboxylative coupling of amino acids with aldehydes and H-dialkylphosphites for the synthesis of α- aminophosphonates
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A simple, efficient, and new method is developed for the synthesis of α-aminophosphonates via a three-component, catalyst-free decarboxylative coupling of amino acids with aldehydes and H-dialkyl phosphite. Treatment of amino acids with aldehydes and diethyl phosphite in the absence of catalyst, base, and ligand give α-aminophosphonates in moderate to good yields. This method is simple, rapid, and high-yielding.
- Kaboudin, Babak,Karami, Leila,Kato, Jun-Ya,Aoyama, Hiroshi,Yokomatsu, Tsutomu
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supporting information
p. 4872 - 4875
(2013/09/02)
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- Highly efficient hydrophosphonylation of aldehydes and unactivated ketones catalyzed by methylene-linked pyrrolyl rare earth metal amido complexes
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A series of rare earth metal amido complexes bearing methylene-linked pyrrolyl-amido ligands were prepared through silylamine elimination reactions and displayed high catalytic activities in hydrophosphonylations of aldehydes and unactivated ketones under
- Zhou, Shuangliu,Wu, Zhangshuan,Rong, Jiewei,Wang, Shaowu,Yang, Gaosheng,Zhu, Xiancui,Zhang, Lijun
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supporting information; experimental part
p. 2653 - 2659
(2012/04/04)
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