- 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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- 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 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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- 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, 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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- Exploration of the SAR of anti-invasive chalcones: Synthesis and biological evaluation of conformationally restricted analogues
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In order to get a clearer view on the active geometry of anti-invasive chalcones, we have prepared a number of isoxazoles and related substances as conformationally restrained mimics of 1,3-diarylpropenones, and also of (Z)-stilbenes. In vitro anti-invasi
- Roman, Bart I.,Ryck, Tine De,Dierickx, Laura,Vanhoecke, Barbara W.A.,Katritzky, Alan R.,Bracke, Marc,Stevens, Christian V.
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experimental part
p. 4812 - 4819
(2012/09/08)
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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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- Reactions of acyl phosphonates with organoaluminum reagents: A new method for the synthesis of secondary and tertiary α-hydroxy phosphonates
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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.
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experimental part
p. 3464 - 3469
(2011/06/19)
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- Synthesis and herbicidal activity of novel dialkoxyphosphoryl aryl methyl 2-(4,6-dimethoxypyrimidin-2-yloxy) benzoate derivatives
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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
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experimental part
p. 1397 - 1403
(2011/10/04)
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- Synthesis and antimicrobial activity of bisphosphonates
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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)
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- The preparation of dimethyl α-hydroxyphosphonates and the chemical shift non-equivalence of their diastereotopic methyl ester groups
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Dimethyl α-hydroxyalkyl-, α-hydroxybenzyl-, α-hydroxyfurfuryl-, and α-hydroxy-α-thienylmethyl-phosphonates have been prepared in good yield by the alumina-catalyzed reaction of dimethyl phosphite with the corresponding alkanals, aryl aldehydes (or aryl methyl ketones), furfuraldehyde, and 2- or 3-thiophenecarboxaldehyde, respectively, thus confirming the general utility of this synthetic procedure. The 1H and 13C nmr spectra of the products exhibit characteristic chemical shift non-equivalence of the diastereotopic methyl ester groups, for which a tentative order of non-equivalence is reported and discussed. Copyright Taylor & Francis Group, LLC.
- Hudson, Harry R.,Yusuf, Ramon O.,Matthews, Ray W.
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experimental part
p. 1527 - 1540
(2009/05/30)
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- Synthesis and herbicidal activity of α-[2-(fluoro-substituted phenoxy)propionyloxy] alkyl phosphonates
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Eight of novel fluoro-substituted phosphonate derivatives were synthesized and the preliminary bioassay indicated that these compounds exhibited herbicidal activities. Copyright Taylor & Francis Group, LLC.
- Li, Yan-Jun,He, Hong-Wu
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body text
p. 712 - 713
(2009/04/05)
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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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