5276-94-8Relevant academic research and scientific papers
Structure-based design, synthesis, and evaluation of the biological activity of novel phosphoroorganic small molecule IAP antagonists
?upicka-S?owik, Agnieszka,Psurski, Mateusz,Grzywa, Renata,Cuprych, Monika,Ciekot, Jaros?aw,Goldeman, Waldemar,Wojaczyńska, El?bieta,Wojaczyński, Jacek,Oleksyszyn, Józef,Sieńczyk, Marcin
, p. 1350 - 1364 (2020/04/24)
One of the strategies employed by novel anticancer therapies is to put the process of apoptosis back on track by blocking the interaction between inhibitor of apoptosis proteins (IAPs) and caspases. The activity of caspases is modulated by the caspases themselves in a caspase/procaspase proteolytic cascade and by their interaction with IAPs. Caspases can be released from the inhibitory influence of IAPs by proapoptotic proteins such as secondary mitochondrial activator of caspases (Smac) that share an IAP binding motif (IBM). The main purpose of the present study was the design and synthesis of phosphorus-based peptidyl antagonists of IAPs that mimic the endogenous Smac protein, which blocks the interaction between IAPs and caspases. Based on the structure of the IAP antagonist and recently reported thiadiazole derivatives, we designed and evaluated the biochemical properties of a series of phosphonic peptides bearing the N-Me-Ala-Val/Chg-Pro-OH motif (Chg: cyclohexylglycine). The ability of the obtained compounds to interact with the binding groove of the X-linked inhibitor of apoptosis protein baculovirus inhibitor of apoptosis protein repeat (XIAP BIR3) domain was examined by a fluorescence polarization assay, while their potential to induce autoubiquitination followed by proteasomal degradation of cellular IAP1 was examined using the MDA-MB-231 breast cancer cell line. The highest potency against BIR3 was observed among peptides containing C-terminal phosphonic phenylalanine analogs, which displayed nanomolar Ki values. Their antiproliferative potential as well as their proapoptotic action, manifested by an increase in caspase-3 activity, was examined using various cell lines.
Microwave-assisted synthesis of N,N-bis(phosphinoylmethyl)amines and N,N,N-tris(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms
Bálint, Erika,Tripolszky, Anna,Heged?s, László,Keglevich, Gy?rgy
supporting information, p. 469 - 473 (2019/03/07)
A family of N,N-bis(phosphinoylmethyl)amines bearing different substituents on the phosphorus atoms was synthesized by the microwave-assisted and catalyst-free Kabachnik–Fields reaction of (aminomethyl)phosphine oxides with paraformaldehyde and diphenylphosphine oxide. The three-component condensation of N,N-bis(phosphinoylmethyl)amine, paraformaldehyde and a secondary phosphine oxide affording N,N,N-tris(phosphinoylmethyl)amine derivatives was also elaborated. This method is a novel approach for the synthesis of the target products.
Reduction of Tertiary Phosphine Oxides by BH 3 Assisted by Neighboring Activating Groups
Sowa, Sylwia,Stankevi?, Marek,Flis, Anna,Pietrusiewicz, K. Micha?
, p. 2106 - 2118 (2018/02/28)
Tertiary sulfanylphosphine and aminoalkylphosphine oxides can be easily converted into the corresponding tertiary sulfanylphosphine- and aminoalkylphosphine-boranes, respectively, through the facile P=O bond reduction by borane complexes. The easy reduction of the strong P=O bond by BH 3, a mild reducing agent, has been achieved through an intramolecular P=O - B complexation directed by proximal SH or NH activating groups located at the α- or β-position to the P=O bond. A generalized reduction mechanism has been proposed.
NOVEL PYRROLE DERIVATIVES AND THEIR SYNTHESIS
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Page/Page column 3, (2011/11/06)
The present invention relates to two novel pyrrole derivatives [3-Phenyl-4-(phenylcarbamoyl)-2-(4-fluorophenyl)-5-(1-methylethyl)-pyrrole-1-yl]methyl(diphenyl)phosphine oxide and Diethyl [3-Phenyl-4-(phenylcarbamoyl)-2-(4-fluorophenyl)-5-(1-methylethyl)-pyrrole-1-yl]methylphosphonate. These pyrrole derivatives can be used as intermediates for the synthesis of the anticholesterol drug atorvastatin.
Asymmetric Michael addition catalyzed by D-glucose-based azacrown ethers
Novák,Tatai,Bakó,Czugler,Keglevich,Toke
, p. 424 - 426 (2007/10/03)
Novel sugar-based azacrown ethers with phosphinoxido-alkyl side chain (2a-e) have been synthesized. They show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2-nitropropane to chalcone (95% ee) and to 3-fur-2-yl-1-phenyl-propenone (80% ee).
Synthesis of new phosphorus 2,4,5-imidazolidinetriones
Plenat, Francoise,Cassagne, Murielle,Cristau, Henri Jean
, p. 9551 - 9558 (2007/10/02)
Phosphorus 2,4,5-imidazolidinetriones are obtained in two different ways: the synthesis of dithiophosphate and phosphonium salt derivatives involves the reaction between a common N-chloromethyl heterocycle and corresponding phosphorus partners, while the
Diphenylphosphinoyl-Substituted Ylides. 1. Thermal 1,3-Dipolar Cycloaddition of α-(Diphenylphosphinoyl)glycine Ester Imines. Dipole Formation as the Rate-Determining Step.
Es, J. J. G. Steven van,Jaarsveld, Korien,Gen, Arne van der
, p. 4063 - 4069 (2007/10/02)
The thermal 1,3-dipolar cycloaddition of N-benzylidene-α-(diphenylphosphinoyl)glycine esters 4 to N-phenylmaleimide is described.With this reactive dipolarophile, dipole formation is the rate-determining step.Addition to less reactive dipolarophiles is co
