- An efficient and simple strategy toward the synthesis of highly functionalized compounds
-
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
-
p. 978 - 995
(2021/08/06)
-
- The typical crystal structures of a few representative α-aryl-α-hydroxyphosphonates
-
The crystal structures of seven α-aryl-α-hydroxyphosphonates synthesized by the Pudovik reaction of substituted benzaldehydes and dialkyl phosphites, namely dimethyl [(hydroxy) (phenyl) methyl] phosphonate, C9H13O4P, dimet
- Rádai, Zita,Kiss, Nóra Zsuzsa,Czugler, Mátyás,Karaghiosoff, Konstantin,Keglevich, Gy?rgy
-
p. 283 - 293
(2019/02/19)
-
- Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes
-
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
-
supporting information
p. 14028 - 14035
(2019/09/18)
-
- Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation
-
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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- Phosphorylation of (1-aryl-1-hydroxymethyl)phosphonates
-
The reaction of dimethyl (1-aryl-1-hydroxymethyl)phosphonates with 1-chloro-3-phospholene 1-oxides, diphenylphosphinic chloride or diphenyl chloridophosphonate affords the corresponding (1-phosphoryloxymethyl)phosphonates. The products with two different
- Rádai, Zita,Hodula, Viktória,Kiss, Nóra Zsuzsa,Kóti, János,Keglevich, Gy?rgy
-
p. 153 - 154
(2019/04/25)
-
- Rational synthesis of α-hydroxyphosphonic derivatives including dronic acids
-
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
-
p. 386 - 387
(2019/01/18)
-
- Synthesis, spectroscopic characterization, and in vitro antibacterial evaluation of novel functionalized sulfamidocarbonyloxyphosphonates
-
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
-
supporting information
p. 1 - 14
(2018/07/31)
-
- Phosphono-replaced methyl alcohol derivative, and preparation method and application thereof
-
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.
- -
-
Paragraph 0017
(2017/08/28)
-
- 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
-
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
-
-
- Synthesis and insecticidal activities of O,O-dialkyl-2-[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carbonyloxy] (aryl) methylphosphonates
-
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
-
p. 1362 - 1367
(2016/09/28)
-
- 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
-
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)
-
- Phospha-Michael Addition to in Situ Prepared 5-Arylmethylidene Meldrum's Acids
-
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
-
p. 1331 - 1334
(2014/06/10)
-
- Magnetic Fe3O4 nanoparticle-supported phosphotungstic acid as a recyclable catalyst for the kabachnik-fields reaction of isatins, imines, and aldehydes under solvent-free conditions
-
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.
-
p. 1753 - 1760
(2015/02/02)
-
- Synthesis and biological activities of O, O-dialkyl 1-((4,6- Dichloropyrimidin-2-yl)carbamyloxy) alkylphosphonates
-
(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)
-
- Mechanistic approach for expeditious and solvent-free synthesis of α-hydroxy phosphonates using potassium phosphate as catalyst
-
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.
-
p. 148 - 152
(2013/04/24)
-
- Synthesis, characterization and catalytic properties of magnetic nanoparticle supported guanidine in base catalyzed synthesis of α-hydroxyphosphonates and α-acetoxyphosphonates
-
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
-
-
- Synthesis and herbicidal activities of sodium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates
-
A series of sodium hydrogen 1-(substituted phenoxyacetoxy) alkylphosphonates was designed and synthesized. The test for herbicidal activity indicated that most of the phosphonates (8) possessed excellent postemergence herbicidal activities against broadleaf weeds. Especially, 8f and 8g showed the best herbicidal activity against rape and amaranth with more than 95% inhibitory rate. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Long, Qingwu,Deng, Xiaoyan,Gao, Yujiao,Xie, Huayong,He, Hongwu,Peng, Hao
-
p. 819 - 825
(2013/08/23)
-
- Synthesis and herbicidal activities of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates
-
A series of lithium or potassium hydrogen 1-(substituted phenoxyacetoxy)alkylphosphonates were designed and synthesized. All the title compounds were identified by IR, 1H NMR, and 31P NMR, some of them were further analyzed by MS and elemental analyses. The test for herbicidal activity indicated that most of the phosphonates (8) possessed excellent postemergence herbicidal activities against broadleaf weeds. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Peng, Hao,Long, Qingwu,Deng, Xiaoyan,He, Hongwu
-
p. 1868 - 1874
(2013/11/06)
-
- Superparamagnetic magnesium ferrite nanoparticles: A magnetically reusable and clean heterogeneous catalyst
-
A highly efficient magnetically recoverable nano-catalyst was fabricated. The material synthesized has been fully characterized by vibrating sample magnetometry (VSM), X-ray powder diffraction, scanning and transmission electron microscopy, FT-IR, and the
- Sheykhan, Mehdi,Mohammadnejad, Hossein,Akbari, Jafar,Heydari, Akbar
-
experimental part
p. 2959 - 2964
(2012/07/30)
-
- Nafion-supported oxovanadium-catalyzed hydrophosphonylation of aldehydes under solventless conditions
-
A Nafion resin-supported oxovanadium(IV) catalyst was readily prepared via ion-exchange method. This solid vanadyl perfluorinated sulfonate catalyst was used as an efficient and recoverable catalyst for the hydrophosphonylation of various aldehydes under solventless conditions at room temperature. The catalyst could be recovered by simple filtration and reused without a significant loss of activity.
- Weng, Shiue-Shien,Lin, Guan-Ying,Li, Hsin-Chun,Yang, Kuo-Chen,Yang, Teng-Mao,Liu, Hui-Chi,Sie, Syuan-Hua
-
p. 455 - 460
(2012/10/29)
-
- A study on the kabachnik - Fields reaction of benzaldehyde, cyclohexylamine, and dialkyl phosphites
-
The Kabachnik-Fields reaction of benzaldehyde, cyclohexylamine, and dimethyl phosphite carried out at 80°C in acetonitrile takes place via an imine (PhCi£Ni-cHex) intermediate, as the monitoring by in situ Fourier transform IR spectroscopy suggested. The corresponding α-hydroxyphosphonate was also formed in a quantity of 13% that was not converted to α-aminophosphonate under the conditions applied. The outcome was similar to the Kabachnik-Fields reaction with diethyl phosphite as the P-component. Molecular modeling and subsequent DFT calculations carried out under solventless conditions supported the experimental results and indicated the formation of a high number of ideally positioned H bonds as the key determinant for the conformation of the starting, intermediate, and product states. The relative energies of the possible intermediates were in accord with the observation that the formation of the α-hydroxyphosphonate is a "dead-end" route.
- Keglevich, Gyoergy,Kiss, Nora Zsuzsa,Menyhard, Dora K.,Fehervari, Andras,Csontos, Istvan
-
experimental part
p. 171 - 178
(2012/07/14)
-
- Synthesis and herbicidal activity of O,O-dimethyl-(3-phenacryloyloxy) alkyl phosphonates
-
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
-
scheme or table
p. 135 - 141
(2012/05/04)
-
- MgCl2/Et3N base system as a new catalyst for the synthesis of α-hydroxyphosphonate
-
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
-
experimental part
p. 827 - 829
(2012/05/21)
-
- Reactions of acyl phosphonates with organoaluminum reagents: A new method for the synthesis of secondary and tertiary α-hydroxy phosphonates
-
The reactions of organoaluminum reagents (trimethylaluminum, triethylaluminum, etc.) with aryl and alkyl acyl phosphonates, which lead to the formation of α-hydroxy phosphonates in moderate to good yields, are reported. This method provides easy access to
- Seven, Ozlem,Polat-Cakir, Sidika,Hossain, Md. Shakhawoat,Emrullahoglu, Mustafa,Demir, Ayhan S.
-
experimental part
p. 3464 - 3469
(2011/06/19)
-
- N-heterocyclic carbene catalyzed hydrophosphonylation of aldehydes
-
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
-
experimental part
p. 2073 - 2078
(2011/08/05)
-
- METHODS AND SYSTEMS FOR PREPARING IRREVERSIBLE INHIBITORS OF PROTEIN TYROSINE PHOSPHATASES
-
Described herein are the preparation and use of novel bromo- phosphonomethylphenylalanine amino acid derivatives (BrPmp) and BrPmp-containing peptides as specific, irreversible protein tyrosine phosphatase inhibitors, which are suitable for application in peptide synthesis. These derivatives are particularly advantageous since their synthesis is both easy and scalable, and they are suitable for peptide synthesis. The BrPmp derivatives described herein can be appropriately protected to allow for solid phase peptide synthesis (SPPS) and incorporation into peptides for preparation of protein tyrosine phosphatase inhibitors and inhibitor libraries. The peptides and peptide libraries can be used to identify new protein tyrosine phosphatase specific sequences and profile protein tyrosine phosphatase activity in cell lysates, diagnostic samples and biopsy samples.
- -
-
Page/Page column 27
(2011/10/03)
-
- Synthesis and herbicidal activity of novel dialkoxyphosphoryl aryl methyl 2-(4,6-dimethoxypyrimidin-2-yloxy) benzoate derivatives
-
A series of dialkoxyphosphoryl aryl methyl 2-(4,6-dimethoxy-pyrimidin-2- yloxy) benzoate derivatives was designed and synthesized. All new compounds were identified by elemental analysis, infrared (IR), 1H-NMR, and mass spectrometry (MS). Their herbicidal
- Jin, Chuanfei,He, Hongwu
-
experimental part
p. 1397 - 1403
(2011/10/04)
-
- Molecular basis of chiral acid recognition by Candida rugosa lipase: X-ray structure of transition state analog and modeling of the hydrolysis of methyl 2-methoxy-2-phenylacetate
-
Lipase from Candida rugosa shows high enantioselectivity toward α-substituted chiral acids such as 2-arylpropionic acids. To understand how Candida rugosa lipase (CRL) distinguishes between enantiomers of chiral acids, we determined the X-ray crystal stru
- Colton, Ian J.,Yin,Grochulski, Pawel,Kazlauskas, Romas J.
-
experimental part
p. 2529 - 2544
(2011/11/29)
-
- Microwave-assisted synthesis of α-hydroxybenzylphosphonates and -benzylphosphine oxides
-
A series of α-hydroxy-benzylphosphonates and -benzylphosphine oxides was synthesized by the Na2CO3-catalyzed microwave-assisted addition of dialkyl phosphites and dipenylphosphine oxide to P-substituted benzaldehydes. The solventless reaction provided the products in short reaction times and in 71-88% yield.
- Keglevich, Gyoergy,Toth, Viola Roza,Drahos, Laszo
-
experimental part
p. 15 - 17
(2011/10/09)
-
- Studies of O,O-Dimethyl α-(2,4-Dichlorophenoxyacetoxy) ethylphosphonate (HW02) as a new herbicide. 1. Synthesis and herbicidal activity of HW02 and analogues as novel inhibitors of pyruvate dehydrogenase complex
-
On the basis of the previous work for optimization of O,O-diethyl α-(substituted phenoxyacetoxy)alkylphosphonates, further extensive syntheticmodifications were made to the substituents in alkylphosphonate and phenoxymoieties of the title compounds. New O,O-dimethyl α-(substituted phenoxyacetoxy)alkylphosphonates were synthesized as potential inhibitors of pyruvate dehydorogenase complex (PDHc). Their herbicidal activity and efficacy in vitro against PDHc were examined. Some of these compounds exhibited significant herbicidal activity and were demonstrated to be effective inhibitors of PDHc from three different plants. The structure-activity relationships of these compounds including previously reported analogous compoundswere studied by examining their herbicidal activities. Both inhibitory potency against PDHc and herbicidal activity of title compounds could be increased greatly by optimizing substituent groups of the title compounds. O,O-Dimethyl α-(2,4- dichlorophenoxyacetoxy)ethylphosphonate (I-5), which acted as a competitive inhibitor of PDHc with much higher inhibitory potency against PDHc from Pisum sativum and Phaseolus radiatus than from Oryza sativa, was found to be themost effective compound against broadleaf weeds and showed potential utility as herbicide.
- He, Hong-Wu,Yuan, Jun-Lin,Peng, Hao,Chen, Ting,Shen, Ping,Wan, Shu-Qing,Lee, Yanjun,Tan, Hong-Liang,He, Ya-Hui,He, Jun-Bo,Li, Yan
-
scheme or table
p. 4801 - 4813
(2011/12/04)
-
- Pyridine 2,6-dicarboxylic acid as a bifunctional organocatalyst for hydrophosphonylation of aldehydes and ketones in water
-
A novel organocatalytic, direct synthesis of α-hydroxy phosphonates via reaction of aldehydes and ketones with trimethylphosphite in the presence of catalytic amounts of pyridine 2,6-dicarboxylic acid in water is reported. The method is simple, cost-effec
- Jahani, Fatemeh,Zamenian, Behi,Khaksar, Samad,Tajbakhsh, Mahmood
-
experimental part
p. 3315 - 3318
(2010/11/18)
-
- A protected l-bromophosphonomethylphenylalanine amino acid derivative (BrPmp) for synthesis of irreversible protein tyrosine phosphatase inhibitors
-
Protein tyrosine phosphatases (PTPs) are important therapeutic targets for medicinal chemists and biochemists. General strategies for the development of inhibitors of these enzymes are needed. Several modular strategies which rely on phosphotyrosine mimics are known for PTP inhibitors. Previous strategies include phosphonomethylphenylalanine (Pmp) derivatives which act as competitive inhibitors. Pmp amino acid derivatives have been used to develop specific inhibitors by incorporation into sequences recognized by the PTP of interest. We report the synthesis of a new phosphonotyrosine analog, l- phosphonobromomethylphenylalanine (BrPmp), which acts as an inhibitor of PTPs. The BrPmp derivative was prepared as an Fmoc-protected amino acid which can be used in standard solid phase peptide synthesis (SPPS) methods. The synthesis of the protected amino acid derivative requires 11 steps from tyrosine with a 30% overall yield. Enzyme inhibition studies with the PTP CD45 demonstrate that BrPmp derivatives are irreversible inhibitors of the enzyme. A tripeptide which incorporated BrPmp had increased inhibitory potency against PTP relative to BrPmp alone, confirming that the incorporation of BrPmp into peptide sequences provides additional context to improve enzyme binding.
- Tulsi, Naresh S.,Downey, A. Michael,Cairo, Christopher W.
-
experimental part
p. 8679 - 8686
(2011/02/25)
-
- Synthesis, characterizations, and crystal structures of α-hydroxyphosphonic acid esters
-
This article describes the synthesis of -hydroxyphosphonic acid esters using the Pudovik reaction. IR, 1H NMR, 13C NMR, 31P NMR, MS, and elemental analysis were employed to confirm their structures. X-ray structure analysi
- Fang, Hua,Chen, Weizhu,Hong, Bihong,Zhao, Yufen,Fang, Meijuan
-
experimental part
p. 2182 - 2193
(2010/12/25)
-
- Synthesis and antimicrobial activity of bisphosphonates
-
Dimethyl [(substitutedphenyl)(6-oxo6λ5dibenzo[d,f][1,3,2] dioxaphophepin-6-yl)methyl]phosphonates (5a-j) were synthesised through a three step process involving preparation of dimethyl hydroxy(substitutedphenyl) methylphosphonates (4a-j) and their reactio
- Reddy, M.Veera Narayana,Reddy, K.R. Kishore Kumar,Reddy, C.Bhupendra,Kumar, B.Siva,Reddy, C.Suresh,Reddy, C.Devendranath
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experimental part
p. 258 - 260
(2009/12/03)
-
- Synthesis and biological activity of O,O-Dimethyl-2,6-Pyridinyl diformyloxy alkyl phosphonates
-
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
-
scheme or table
p. 2777 - 2785
(2010/04/03)
-
- Organocatalytic synthesis of α-hydroxy and α-aminophosphonates
-
A new and highly flexible procedure is described for the synthesis of α-amino- and α-hydroxy phosphonates. In the presence of a catalytic amount of oxalic acid (10 mol %), trimethyl phosphite reacts with aldehydes or imines (generated in situ from an aldehyde and an amine) to yield the corresponding coupled products in good yield.
- Vahdat, Seyed Mohammad,Baharfar, Robabeh,Tajbakhsh, Mahmood,Heydari, Akbar,Baghbanian, Seyed Meysam,Khaksar, Samad
-
scheme or table
p. 6501 - 6504
(2009/04/06)
-
- Catalytic enantioselective pudovik reaction of aldehydes and aldimines with tethered bis(8-quinolinato) (TBOx) aluminum complex
-
New chiral tethered bis(8-quinolinolato) (TBOx) aluminum(III) complexes effectively catalyze the addition of phosphites to aldehydes and aldimines to give enantioenriched α-hydroxy and α-amino phosphonates in high yields and enantioselectivities with unpr
- Abell, Joshua P.,Yamamoto, Hisashi
-
supporting information; experimental part
p. 10521 - 10523
(2009/02/04)
-
- Straightforward synthesis of a new series of α-(arylamino thiocarbonyloxy) hydrocarbylphosphonates
-
A convenient, straightforward, two-step reaction of α- hydroxyhydrocarbylphosphonates with arylisothiocyanates in the presence of catalytic amounts of sodium methoxide in 1,2-dichloroethane as solvent produced various new α-(arylamino thiocarbonyloxy) hyd
- Li, Jian-Ping,Zhu, Jun-Ge,Liu, Rui-Jie,Cui, Feng-Ling,Liu, Ping,Liu, Guo-Sheng
-
-
- Synthesis of novel bicycli caged phosphate derivatives
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A series of bicycli caged phosphates were synthesized, and biological activity test showed that the title compounds exhibited moderate herbicidal activity. Copyright Taylor & Francis Group, LLC.
- Mo, Wen-Yan,He, Hong-Wu
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p. 699 - 700
(2009/04/11)
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- Amberlyst-15 as a heterogeneous reusable catalyst for the synthesis of α-hydroxy phosphonates in water
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An efficient and simple synthesis of α-hydroxy phosphonates has been achieved via reaction of aldehydes with trimethylphosphite in the presence of Amberlyst-15 in water. The reaction is highly selective with excellent yields under mild conditions. Georg T
- Tajbakhsh, Mahmood,Heydari, Akbar,Khalilzadeh, Mohammad A.,Lakouraj, Moslem M.,Zamenian, Behi,Khaksar, Samad
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p. 2347 - 2350
(2008/03/12)
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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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- The synthesis and herbicidal evaluation of fluorine-containing phenoxyacetoxyalkylphosphonate derivatives
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To investigate the influence of a fluorine moiety on the biological activity of phenoxyacetoxyalkylphosphonates, a series of fluorine-containing phenoxyacetoxyalkylphosphonates were synthesized and screened for herbicidal activity in a greenhouse. The majority of the title compounds showed better preemergence activity than postemergence activity against the test plants, especially on monocotyledon. Compound 5l exhibited notable activity. Results showed that by introducing a fluorine moiety to the parent structure of phenoxyacetoxyalkylphosphonates, a series of new compounds with satisfactory herbicidal activity could be synthesized. A reasonable combination of a fluorine moiety and other substituents on the benzene ring had a great influence on the herbicidal activity. Copyright Taylor & Francis Group, LLC.
- Chen, Ting,Shen, Ping,Li, Yanjun,He, Hongwu
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p. 2135 - 2145
(2007/10/03)
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- Synthesis and herbicidal activity of O,O-dialkyl phenoxyacetoxyalkylphosphonates containing fluorine
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A series of substituted phenoxyacetoxyalkylphosphonates bearing fluorine were designed and synthesized. All the new compounds were identified by elemental analysis, IR, 1H NMR and MS and were tested for herbicidal activity in greenhouse at a rate of 1.5 kg/ha. The results of preliminary bioassay showed that fluorine moiety introduced to the core structure could help to improve the herbicidal activity, and compounds with a 3-trifluoromethyl in benzene ring exhibited higher inhibitory activity.
- Chen, Ting,Shen, Ping,Li, Yanjun,He, Hongwu
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p. 291 - 295
(2007/10/03)
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- A stereochemical approach to the Kabachnik-Fields reaction mechanism
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A comparison of the diastereomeric composition of Kabachnik-Fields reaction products with those of two reactions simulating its stereo-controlling steps showed that only the 'imine' mechanism works in the (MeO) 2P(O)H-PhCHO-[(S),(R,S)-H2NCH(Ph)Me] system, like in the phosphite-imine system; in a similar system containing (R,S)-sec-butylamine, additional 'nucleophilic amination' of the initially formed α-hydroxybenzyl phosphonate occurs.
- Dimukhametov, Mudaris N.,Bayandina, Evgenia V.,Davydova, Elena Yu.,Gubaidullin, Aidar T.,Litvinov, Igor A.,Alfonsov, Vladimir A.
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p. 150 - 151
(2007/10/03)
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- Lithium perchlorate diethyl ether solution: A highly efficient media for the abramov reaction
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The α-hydroxy phosphonates are readily prepared by treating aromatic or aliphatic aldehydes and ketones with trialkylphosphite in the presence of trimethylsilylchloride in a very short time and in almost quantitative yields.
- Azizi, Najmedin,Saidi, Mohammad R.
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p. 1255 - 1259
(2007/10/03)
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- An efficient route to chiral α- and β-hydroxyalkanephosphonates
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Enzymatic kinetic resolution of α- and β-hydroxyphosphonates in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution. A variety of racemic hydroxyphosphonates were efficiently transformed to the corresponding enantiomerically pure acetates (ee up to 99% and yield up to 87%).
- Pamies, Oscar,Baeckvall, Jan-E.
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p. 4815 - 4818
(2007/10/03)
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- Hydrolysis-stable and polymerizable acrylphosphonic acids
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Hydrolysis-stable and polymerizable acrylphosphonic acids are described which are particularly suitable as a component of dental adhesives owing to their adhesion-promoting properties.
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- The synthesis of 1-hydroxy phosphonates of high enantiomeric excess using sequential asymmetric reactions: Titanium alkoxide-catalyzed P-C bond formation and kinetic resolution
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Titanium alkoxide-catalyzed asymmetric phosphonylation of aldehydes yields hydroxy phosphonates in moderate to good enantiomeric excess (e.e.s ~70%). The hydroxy phosphonates were acetylated and the acetates were subjected to enzyme-catalyzed kinetic resolution. The non-racemic acetates 2 (predominantly (R)-enantiomer) were hydrolyzed with an (R)-enantiomer-selective lipase, resulting predominantly in the hydrolysis of the (R)-isomer (at 85% conversion) to give the alcohols 3 with high e.e. Alternatively, hydrolysis of the minor enantiomeric (S)-acetate to approximately 20% conversion left the enriched (R)-configured acetate with improved e.e. (>90%). The moderate enantioselectivities obtained in the catalytic P-C bond formation are enhanced during the enzymatic hydrolysis. Furthermore, availability of the non-racemic phosphonates permits the use of less selective enzymes, resulting in higher yields in comparison with the standard resolution of racemic materials.
- Rowe, Bradley J.,Spilling, Christopher D.
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p. 1701 - 1708
(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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