- Enantioselective synthesis of α-hydroxy phosphonates via oxidation with (camphorsulfonyl)oxaziridines
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Reaction of phosphonate anions with enantiomerically pure (camphorsulfonyl)oxaziridines results in formation of nonracemic α-hydroxy phosphonates. This enantioselective hydroxylation methodology provides convenient access to optically active α-hydroxy pho
- Pogatchnik, Diana M.,Wiemer, David F.
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Read Online
- 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 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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- Synthesis and insecticidal activities of O,O-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy] (aryl) methylphosphonates
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A series of novel O,O-Dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy](aryl) methy-lphosphonates I-1–14 were designed and synthesized. The structures of all the title compounds were confirmed by 1H-NMR, 13C-NMR, 31P-NMR, IR and elemental analysis. Their insecticidal activities against Mythimna separata and Plutella xylostella were evaluated. The results of bioassays indicated that the title compounds exhibited 20–80% larvicidal activity against Mythimna separata at 1000?mg/L.
- Wang, Wei,Wang, Lie-Ping,Ning, Bin-Ke,Mao, Ming-Zhen,Xue, Chao,Wang, Hai-Yang
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p. 1362 - 1367
(2016/09/28)
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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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- Synthesis, structure, and catalytic activity of titanium complexes with chiral biaryl Schiff-base ligands
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A series of chiral organo-titanium complexes have been prepared from the reaction between Ti(OiPr)4 and chiral biaryl Schiff-base ligands 1H2-12H. The steric demand of the ligand plays an important role in the formation of
- Chen, Liang,Zhao, Ning,Wang, Qiuwen,Hou, Guohua,Song, Haibin,Zi, Guofu
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p. 140 - 155
(2013/07/27)
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- Synthesis, characterization and catalytic properties of magnetic nanoparticle supported guanidine in base catalyzed synthesis of α-hydroxyphosphonates and α-acetoxyphosphonates
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Magnetic nanoparticle Fe3O4-immobilized guanidine (MNPs-Guanidine) as a novel magnetically interphase nanocatalyst was synthesized and characterized. MNPs-Guanidine catalyzed the synthesis of α-hydroxyphosphonates from aldehydes and
- Rostami, Amin,Atashkar, Bahareh,Moradi, Darush
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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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- Synthesis and herbicidal activity of O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates
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In an attempt to discover novel compounds with high biological activity and low toxicity, a series of new O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates 4a-m have been designed and synthesized by the reaction of 3-phenacryloyl chloride with α-hydroxyalkyl phosphonate. All new compounds were characterized by elemental analysis, IR, and 1H NMR spectroscopy as well as by mass spectrometry. The results of preliminary bioassay indicate that some of the target compounds have excellent inhibitory activities on Triticum aestivum (wheat) and Brassica napus L. (rape). Copyright Taylor and Francis Group, LLC.
- Wang, Tao,Huang, Hai Jin,Luo, Jin,Yu, Dan Hong
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scheme or table
p. 135 - 141
(2012/05/04)
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- MgCl2/Et3N base system as a new catalyst for the synthesis of α-hydroxyphosphonate
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An efficient and simple synthesis of α-hydroxyphosphonates via reaction of aldehydes and ketones with dimethylphosphite in the presence of MgCl2/Et3N base system is reported. The use of readily available and easy to handle reagent MgCl2/Et3N makes this method simple, convenient, and practical. Copyright
- Tajbakhsh, Mahmood,Khaksar, Samad,Tafazoli, Zahra,Bekhradnia, Ahmadreza
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experimental part
p. 827 - 829
(2012/05/21)
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- N-heterocyclic carbene catalyzed hydrophosphonylation of aldehydes
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N-Heterocyclic carbene catalyzed Pudovik-type reaction of dimethyl trimethylsilyl phosphite and aldehydes for the construction of carbon-phosphorus bonds have been developed, providing -hydroxyphosphonates in moderate to excellent yield. Georg Thieme Verl
- Cai, Zhi-Hua,Du, Guang-Fen,He, Lin,Gu, Cheng-Zhi,Dai, Bin
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experimental part
p. 2073 - 2078
(2011/08/05)
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- Highly enantioselective hydrophosphonylation of aldehydes: Base-enhanced aluminum-salalen catalysis
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(Chemical Equation Presented) The dimethyl phosphonate hydrophosphonylation of conjugated- and non-conjugated aldehydes into their correspond ing α-hydroxy phosphonates was achieved using chiral aluminum-salalen complex 1 (see scheme).
- Suyama, Keitaro,Sakai, Yoshifumi,Matsumoto, Kazuhiro,Saito, Bunnai,Katsuki, Tsutomu
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supporting information; experimental part
p. 797 - 799
(2010/04/06)
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- Synthesis and biological activity of O,O-Dimethyl-2,6-Pyridinyl diformyloxy alkyl phosphonates
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In an attempt to discover novel compounds with high activity and low toxicity, a series of new O,O-dimethyl-2,6-pyridinyl diformyloxy alkyl phosphonates 4a-4p has been designed and synthesized by the reaction of 2,6-pyridinyl diformyloxy chloride with α-hydroxyalkyl phosphonate. The structures of all new compounds were characterized by elementary analysis, IR, 1H NMR, and MS spectroscopies. The results of a preliminary bioassay indicate that some of the target compounds have obviously promotive action for plant growth against the stalk of barnyard grass.
- Wang, Tao,Lei, Da You,Huang, Ying,Ao, Li Hua
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scheme or table
p. 2777 - 2785
(2010/04/03)
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- 5-Fluorouracil derivatives containing α-hydroxy phosphonates
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In order to find high acitivity and low toxicity antitumor drug-lead compounds, 13 novel N1-(2-furanidyl)-N3-(O,O- dialkylphosphonyl aryl (alkyl)methoxy-carbonylmethyl)-5-fluorouracils were synthesized via phase-transferred catalytic reactions of chloroacetyloxyalkyl phosphonates 2 with N1-(2-furanidyl)-5-fluorouracil. The structures of the products were confirmed by 1H NMR, 31P NMR, IR, and MS spectra and elemental analyses. The results of preliminary bioassay showed that the new compounds possess some extent of inhibitory effect against HCT-8 and Bel-7402 cell lines and good fungicidal activities. Copyright Taylor & Francis Group, LLC.
- Shi, De-Qing,Li, Xiao-Ju,Wei, Jia
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p. 405 - 412
(2007/10/03)
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- Synthesis of an optically active C1-symmetric Al(salalen) complex and its application to the catalytic hydrophosphonylation of aldehydes
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(Chemical Equation Presented) Quite universally: The chiral trigonal-bipyramidal Al(salalen) complex 1 was synthesized and found to be an efficient catalyst for enantioselective hydrophosphonylation of various aldehydes with dimethyl phosphite (see scheme
- Saito, Bunnai,Katsuki, Tsutomu
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p. 4600 - 4602
(2007/10/03)
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- Synthesis and dealkylation of 1 -(dichloro-phenoxyacetoxy) alkyl phosphonates
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Using the silylation procedure with chlorotrimethylsilane/sodium iodide followed by alcoholysis, 1-(dichlorophenoxy acetoxy)alkyl phosphonic acid dimethyl esters can be transformed into the parent phosphonic acids without influence on carboxylate ester group.
- He, Hongwu,Liu, Xufeng,Hu, Liming,Wang, Siquan,Liu, Zhaojie
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p. 633 - 636
(2007/10/03)
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- Asymmetric Synthesis of Chiral, Nonracemic Dialkyl α-Hydroxyarylmethyl- and α-, β- and γ-Hydroxyalkylphosphonates from Keto Phosphonates
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The enantioselective synthesis of α-hydroxyarylmethylphosphonates 2a-p by the oxazaborolidine-catalyzed reduction of α-keto phosphonates 1a-p using different boranes 4a-c was studied in detail.Moderate to good enantioselectivities are found (up to 80perce
- Meier, Chris,Laux, Wolfgang H. G.,Bats, Jan W.
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p. 1963 - 1980
(2007/10/03)
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- THE ABSOLUTE CONFIGURATION OF α-HYDROXYPHOSPHONATES
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The absolute configuration and CD spectra of a series of chiral α-hydroxyphosphonates and phosphoric acids have been determinated.The hydroxyphosphonates were prepared via a quinine catalyzed 1,2-addition reaction of phosphite to aldehyde.
- Smaardijk, Ab. A.,Noorda, Simon,Bolhuis, Fre van,Wynberg, Hans
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p. 493 - 496
(2007/10/02)
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