1663-55-4Relevant articles and documents
Enantioselective synthesis of α-hydroxyalkylphosphonates
Nesterov,Kolodyazhnyi
, p. 1161 - 1162 (2005)
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Stereoselective Aldol Reactions via Enolates of α-Acylphosphonate Diesters
Longmire, Cynthia F.,Evans, Slayton A.
, p. 922 - 923 (1990)
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.
1,1,2-Triphenyl-1,2-ethanediol: A host for carboxylic acids and amides in coordinatoclathrates
Ridder, Daniel,Wunderlich, Hartmut,Braun, Manfred
, p. 1071 - 1076 (1998)
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
A study on the Kabachnik-Fields reaction of benzaldehyde, propylamine, and diethyl phosphite by in situ Fourier transform IR spectroscopy
Keglevich, Gyoergy,Fehervari, Andras,Csontos, Istvan
, p. 599 - 604 (2011)
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
Efficient synthesis of ether phosphonates using trichloroacetimidate and acetate coupling methods
Fathalla, Walid,Ali, Ibrahim A. I.,Pazdera, Pavel
, p. 7385 - 7395 (2018)
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.
Synthesis of novel α-hydroxyphosphonates along with α-aminophosphonates as intermediates
Belovics, Alexandra,H?gele, Gerhard,Keglevich, Gy?rgy,Varga, Petra R.
, (2021/12/22)
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.
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
supporting information, 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.