1127-41-9Relevant academic research and scientific papers
New (α-hydroxyalkyl)phosphorus amphiphiles: Synthesis and dissociation constants
Albouy, Dominique,Brun, Alice,Munoz, Aurelio,Etemad-Moghadam, Guita
, p. 7223 - 7230 (1998)
Direct synthesis of free (α-hydroxyalkyl)phosphinic acid amphiphiles 1 can be readily realized by sonication of the heterogeneous mixture of 50% aqueous hypophosphorous acid and long-chain aldehydes in the presence of catalytic amounts of hydrochloric aci
Protection of Phosphonate Function by Means of Ethoxycarbonyl Group. A New Method for Generation of Reactive Silyl Phosphite Intermediates
Sekine, Mitsuo,Mori, Hiroyuki,Hata, Tsujiaki
, p. 239 - 242 (1982)
Nucleoside ethoxycarbonylphosphonates were prepared by condensation of appropriately protected nucleosides with ethoxycarbonylphosphonic acid.They were easily converted by treatment with 1 M NaOH followed by trimethylsilylation to highly reactive bis(trimethylsilyl) nucleoside phosphite intermediates which were allowed in situ to react with water, diphenyl disulfide, 2,2'-dipyridyl disulfide, and aldehydes to afford the corresponding nucleoside phosphonates, nucleoside S-phenyl phosphorothioates, nucleoside phosphates, and nucleoside α-hydroxy phosphonates in good yields, respectively.The nucleoside phosphonates were further converted to nucleosides under mild acidic conditions.Thus, the ethoxycarbonyl group proved to serve as a versatile protecting group for not only H-P(O) but also HO-P(O) and hydroxy groups of sugars.
Direct Approach to α-Hydroxyphosphonic and α,ω-Dihydroxyalkane-α,ω-bisphosphonic Acids by the Reduction of (Bis)acylphosphonic Acids
Chen, Ravit,Breuer, Eli
, p. 5107 - 5109 (1998)
Acylphosphonic and bisacylphosphonic acid sodium salts were directly reduced by sodium borohydride to the corresponding hydroxyphosphonates and dihydroxyalkanebisphosphonates. The solution conformation of the (bis)hydroxyphosphonic acid sodium salts, eluc
Synthesis, spectral analysis, theoretical studies, molecular dynamic simulation and comparison of anticorrosive activity of an ester and an acid α-Hydroxyphosphonates
Bourzami, Riadh,Ouksel, Louiza,Chafai, Nadjib
, p. 839 - 849 (2019)
Diethyl [hydroxy (phenyl) methyl] phosphonate ester (DHPMP) and [hydroxy (phenyl) methyl] phosphonate acid (HPMPA) have been synthetized and their structures were confirmed by IR, UV–Vis, 1H, 13C and 31P NMR spectroscopies
Silyl Phosphite Equivalents: 2,2,2-Trichloroethoxycarbonylphosphonates
Sekine, Mitsuo,Yamagata, Hiraku,Hata, Tsujiaki
, p. 970 - 971 (1981)
2,2,2-Trichloroethoxycarbonylphosphonates were converted directly by treatment with Zn-Me3SiCl into silyl phosphites which in situ reacted with aldehydes to give α-hydroxyphosphonates in good yields.
Hydrolysis and alcoholysis of phosphinates and phosphonates
Harsági, Nikoletta,Keglevich, Gy?rgy,Sz?ll?si, Betti,Varga, Petra Regina
, (2021/11/04)
Phosphinic and phosphonic acids useful intermediates and biologically active compounds may be prepared from their esters: phosphinates and phosphonates, respectively, by acid-catalyzed hydrolysis either on conventional heating or on MW irradiation. The transesterification of alkyl phosphinates took place only in the presence of suitable ionic liquids as the catalysts. In the cases of phenylphosphonates, depending on the nature of the ionic liquid, the formation of the ester was accompanied by the fission of the C–O bond.
Optimization and a Kinetic Study on the Acidic Hydrolysis of Dialkyl α-Hydroxybenzylphosphonates
Harsági, Nikoletta,Rádai, Zita,Szigetvári, áron,Kóti, János,Keglevich, Gy?rgy
, (2020/09/04)
The two-step acidic hydrolysis of α-hydroxybenzylphosphonates and a few related derivatives was monitored in order to determine the kinetics and to map the reactivity of the differently substituted phosphonates in hydrolysis. Electron-withdrawing substituents increased the rate, while electron-releasing ones slowed down the reaction. Both hydrolysis steps were characterized by pseudo-first-order rate constants. The fission of the second P-O-C bond was found to be the rate-determining step.
Synthesis and anticancer cytotoxicity with structural context of an α-hydroxyphosphonate based compound library derived from substituted benzaldehydes
Rádai, Zita,Windt, Tímea,Nagy, Veronika,Füredi, András,Kiss, Nóra Zsuzsa,Ranelovi?, Ivan,Tóvári, József,Keglevich, Gy?rgy,Szakács, Gergely,Tóth, Szilárd
, p. 14028 - 14035 (2019/09/18)
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.
Green synthesis and cytotoxic activity of dibenzyl α-hydroxyphosphonates and α-hydroxyphosphonic acids
Rádai, Zita,Szeles, Petra,Kiss, Nóra Zsuzsa,Heged?s, László,Windt, Tímea,Nagy, Veronika,Keglevich, Gy?rgy
, (2018/09/25)
A series of dibenzyl α-hydroxyphosphonates and the corresponding α-hydroxyphosphonic acids, mostly new compounds, have been synthesized. The dibenzyl α-hydroxyphosphonates have been obtained in the Pudovik reaction of substituted benzaldehydes and dibenzyl phosphite in the presence of triethylamine as the catalyst. The amount of the solvent was minimized during the reaction, and the workup involved crystallization from the reaction mixture. A new protocol was developed to transform the dibenzyl 1-hydroxyphosphonates to the corresponding phosphonic acids by catalytic hydrogenation. The derivatives prepared were screened as potential cytotoxic agents against Mes-Sa human uterine sarcoma cell line.
Isoprenoid Biosynthesis Inhibitors Targeting Bacterial Cell Growth
Desai, Janish,Wang, Yang,Wang, Ke,Malwal, Satish R.,Oldfield, Eric
, p. 2205 - 2215 (2016/10/22)
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.
