49640-96-2Relevant articles and documents
Binding modes of reverse fosmidomycin analogs toward the antimalarial target IspC
Konzuch, Sarah,Umeda, Tomonobu,Held, Jana,H?hn, Saskia,Brücher, Karin,Lienau, Claudia,Behrendt, Christoph T.,Gr?wert, Tobias,Bacher, Adelbert,Illarionov, Boris,Fischer, Markus,Mordmüller, Benjamin,Tanaka, Nobutada,Kurz, Thomas
, p. 8827 - 8838 (2014)
1-Deoxy-d-xylulose 5-phosphate reductoisomerase of Plasmodium falciparum (PfIspC, PfDxr), believed to be the rate-limiting enzyme of the nonmevalonate pathway of isoprenoid biosynthesis (MEP pathway), is a clinically validated antimalarial target. The enzyme is efficiently inhibited by the natural product fosmidomycin. To gain new insights into the structure activity relationships of reverse fosmidomycin analogs, several reverse analogs of fosmidomycin were synthesized and biologically evaluated. The 4-methoxyphenyl substituted derivative 2c showed potent inhibition of PfIspC as well as of P. falciparum growth and was more than one order of magnitude more active than fosmidomycin. The binding modes of three new derivatives in complex with PfIspC, reduced nicotinamide adenine dinucleotide phosphate, and Mg2+ were determined by X-ray structure analysis. Notably, PfIspC selectively binds the S-enantiomers of the study compounds.
Synthesis, supramolecular structure, spectral properties and correlation between nonlinear optic, thermochemistry and thermal behavior of an α-Hydroxyphosphonate acid ester, dual experimental and DFT approaches
Boudjada, Ali,Bourzami, Riadh,Hamdouni, Noudjoud,Ouksel, Louiza
, (2021)
First, we note in this paper that α-Hydroxyphosphonate acid ester was synthesized before; we confirmed it by a new method and its various properties are discussed experimentally and theoretically. The structure of Diethyl [hydroxy(4-methoxyphenyl) methyl] phosphonate (DH4MPMP) resolved by SXRD is compared to the optimized geometry, the FT-IR, NMR, UV-Vis spectroscopies results were compared and discussed experimentally and theoretically. The Hirshfeld surface analyses were employed to determine qualitative and quantitative intermolecular interactions present in the solid state and through, the supramolecular 3D-network was discussed. The UV-Vis spectrum exhibit a strong absorption in middle UV domain and an optical transmittance in the visible one. To be close from the experimental results, all DFT calculations based on B3LYP/6-31G (d,p) were detailed on monomer and dimer models. The DFT calculation of the second-order nonlinear optical properties is based on the first static hyperpolarizability (β), the results show that the material might have nonlinear optical properties. The calculated frontier molecular orbitals and their energies were calculated. The research was extended to the calculations of the molecular electrostatic potential map; it shows negative potential areas localized around oxygen atoms as well as the positive localized around the hydrogen atoms. Finally, the thermodynamic functions (entropy, heat capacity and enthalpy) were determined from spectroscopic data by statistical methods in the range 100–1000 K and the experimental thermal decomposition behavior was analyzed by TGA.
A convenient and mild protocol for preparation of α – trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide
Mitragotri, Satish D.,Kulkarni, Makarand A.,Desai, Uday V.,Wadagaonkar, Prakash P.
, (2021/10/05)
A convenient and mild protocol was developed for the trimethylsilylation of α-hydroxyphosphonates using hexamethyldisilazane as the silylating agent in the presence of sulfamic acid (SA) as a heterogeneous solid acid catalyst in dichloromethane as the rea
O-allylated pudovik and passerini adducts as versatile scaffolds for product diversification
Arseniyadis, Stellios,El Ka?m, Laurent,Kerim, Mansour Dole,Katsina, Tania,Cattoen, Martin,Fincias, Nicolas
supporting information, p. 12514 - 12525 (2020/11/10)
The palladium-catalyzed O-allylation of α-hydroxyphosphonates and α-hydroxyamides obtained from Pudovik and Passerini multicomponent reactions has allowed interesting and highly straightforward access to a variety of building blocks for product diversific
Biocatalytic Promiscuity of Lipases in Carbon-Phosphorus Bond Formation
Koszelewski, Dominik,Ostaszewski, Ryszard
, p. 2554 - 2558 (2019/04/30)
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
CeCl3?7H2O-catalysed hydrophosphonylation of aldehydes and ketones: An expeditious route to α-hydroxyphosphonates under solvent-free conditions
Mahesh,Sharma, Rupali,Kour, Parteek,Kumar, Anil
, p. 1091 - 1097 (2019/07/04)
A cerium(III) chloride-catalysed expeditious synthesis of α-hydroxyphosphonates via a modified Abramov synthetic protocol has been developed. The scope of the current protocol is broad, with a range of aromatic, α,β-unsaturated and heterocyclic aldehydes
Palladium-catalysed O-Allylation of α-Hydroxyphosphonates: An Expedient Entry into Phosphono-oxaheterocycles
Kerim, Mansour Dolé,Cattoen, Martin,Fincias, Nicolas,Dos Santos, Aurélie,Arseniyadis, Stellios,El Ka?m, Laurent
supporting information, p. 449 - 454 (2017/12/04)
We report here an unprecedented palladium-catalysed O-allylation of α-hydroxyphosphonates. The method was eventually included in a sequential Pudovik/Tsuji-Trost type O-allylation/Ring-Closing Metathesis to afford a variety of phosphorylated heterocycles
Hydrophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes
Cabrita, Ivania R.,Florindo, Pedro R.,Costa, Paulo J.,Oliveira, M. Concei??o,Fernandes, Ana C.
, p. 77 - 86 (2018/03/22)
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
Efficient synthesis of ether phosphonates using trichloroacetimidate and acetate coupling methods
Fathalla, Walid,Ali, Ibrahim A. I.,Pazdera, Pavel
, p. 7385 - 7395 (2018/03/01)
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.
Efficient synthesis of α-substituted-α-arylmethyl phosphonates using trichloroacetimidate C–C coupling method
Fathalla, Walid,Pazdera, Pavel,El-Rayes, Samir,Ali, Ibrahim.A.I.
, p. 1681 - 1691 (2018/03/01)
A simple convenient protocol for the synthesis of diethyl α,α-diaryl methylphosphonate derivatives 5a-f, 6b-f, 7a-f and 8a-f, diethyl α-alkenyl α-aryl methylphosphonates 9a-d and 10a-d and α-(oxoalkyl) α-aryl methylphosphonate 11a-d and 12a-d is described. Trichloroacetimidates 3a-d were treated with activated arenes, styrene, allyltrimethylsilane or silylenol ethers C-nucleophiles in the presence TMSOTf to afford the desired products in good yields and short reaction time.
