4669-51-6Relevant articles and documents
NOVEL PHOSPHOROUS (V)-BASED REAGENTS, PROCESSES FOR THE PREPARATION THEREOF, AND THEIR USE IN MAKING STEREO-DEFINED ORGANOPHOSHOROUS (V) COMPOUNDS
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Paragraph 0243; 0246; 0248, (2019/11/04)
The present invention relates to novel phosphorous (V) (P(V)) reagents, methods for preparing thereof, and methods for preparing organophosphorous (V) compounds by using the novel reagents.
Use of phosphorodithioate-based compounds as hydrogen sulfide donors
Park, Chung-Min,Xian, Ming
, p. 127 - 142 (2015/03/04)
Synthetic hydrogen sulfide (H2S) donors are useful research tools as well as potential therapeutic agents. In this chapter, we report the detailed protocols for the synthesis and evaluation of a series of phosphorodithioate-based H2S donors. Fluorescence assays were used to determine H2S release from the donors in both aqueous buffers and in cultured cells. These donors were found to be slow-release donors, much like the well-known GYY4137. These donors also showed some protective effects against hydrogen peroxide (H2O2)-induced oxidative damage in myocytes.
Synthesis and evaluation of phosphorodithioate-based hydrogen sulfide donors
Park, Chung-Min,Zhao, Yu,Zhu, Zhaohui,Pacheco, Armando,Peng, Bo,Devarie-Baez, Nelmi O.,Bagdon, Powell,Zhang, Hui,Xian, Ming
, p. 2430 - 2434 (2013/09/23)
A series of O-aryl- and alkyl-substituted phosphorodithioates were designed and synthesized as hydrogen sulfide (H2S) donors. H2S releasing capability of these compounds was evaluated using fluorescence methods. O-aryl substituted do
Synthesis of a nucleoside phosphorodithioate analogue responsive to microenvironmental changes through chiral induction
Saneyoshi, Hisao,Mashimo, Takushi,Hatano, Ken,Ito, Yoshihiro,Abe, Hiroshi
, p. 1080 - 1083 (2013/04/10)
We have synthesized a 2′-aminomethyl branched-chain sugar nucleoside phosphorodithioate from 2,2′-anhydro uridine and subjected the material to a subsequent cyclization reaction under aqueous conditions using bi-functional linkers. The rate of the cycliza
New, stronger nucleophiles for nucleic acid-templated chemistry: Synthesis and application in fluorescence detection of cellular RNA
Miller, Gregory P.,Silverman, Adam P.,Kool, Eric T.
, p. 56 - 64 (2008/09/18)
Nucleic acid-templated chemistry is a promising strategy for imaging genetic sequences in living cells. Here we describe the synthesis of two new nucleophiles for use in templated nucleophilic displacements with DNA probes. The nucleophilic groups are pho
Syntheses, NMR characterization and semi-empirical structural studies of dithiaphospholane derivatives
Lima, Luiz Carlos Gomez de,Lima, Miriam Bernardes Gomes de,Matos, Robson Mendes,Menezes, Maria doRosario,Raslan, Delio Soares,Souza, Edward de,Souza, Ana Lucia A.B. de
, p. 1 - 14 (2007/10/03)
A new synthetic route for the preparation odf 2-chloro-1,3,2-dithiaphospholane 1 is reported with a better yield that the previous one. A one-pot preparation of S,S'-bis(1,3,2-dithiaphospholane)-1,2-ethanedithiol 2 is also described. These compounds were characterized using multunuclear NMR, mass and IR spectroscopies. Their 1H NMR spectra were fully resolved by NMR spectra simulation. Semi-empirical structural studies suggest that compound 1 is found, at room temperature, as anly one conformar whereas compound 2 can be found, at room temperature, as a mixture of conformers.
Synthesis and Kinetic Evaluation of Inhibitors of the Phosphatidylinositol-Specific Phospholipase C from Bacillus cereus
Matrin, Stephen F.,Wagman, Allan S.
, p. 8016 - 8023 (2007/10/03)
Substrate analogues of phosphatidylinositol (1) were synthesized and evaluated as potential inhibitors of the bacterial phosphatidylinositol-specific phospholipase C (PI-PLC) from Bacillus cereus.The chiral analogues of the water-soluble phospholipid substrate 5 were designed to probe the effects of varying the inositol C-2 hydroxyl group, which generally believed to serve as the nucleophile in the first step of the hydrolysis of phosphatidylinositols by PI-PLC.In the analogues 6-9, the C-2 hydroxyl group on the inositol ring of the phosphatidylinositol derivatives was rationally altered in several ways.Inversion of the stereochemistry at C-2 of the inositol ring led to the scyllo derivative 6.The inositol C-2 hydroxy group was replaced with inversion by a fluorine to produce the scyllo-fluoro inositol 7 and with a hydrogen atom to furnish the 2-deoxy compound 8.The C-2 hydroxyl group was O-methylated to prepare the methoxy derivative 9.The natural inositol configuration at C-2 was retained in the nonhydrolyzable phosphorodithioate analogue 10.The inhibition of PI-PLC by each of these analogues was then analyzed in a continuous assay using D-myo-inositol 1-(4-nitrophenyl phosphate) (25) as a chromogenic substrate.The kinetic parameters for each of these phosphatidylinositol derivatives were determined, and each was found to be a competitive inhibitor with Ki's as follows: 6, 0.2 mM; 10, 0.6 mM; 8, 2.6 mM; 9, 6.6 mM; and 7, 8.8 mM.This study further establishes that the hydrolysis of phosphatidylinositol analogues by bacterial PI-PLC requires not only the presence of a C-2 hydroxyl group on the inositol ring, but the stereochemistry at this position must also correspond to the natural myo-configuration.For future inhibitor design, it is perhaps noteworthy that the best inhibitors 6 and 10 each possess a hydroxyl group at the 2-position.Several of the inhibitors identified in this study are now being used to obtain crystallographic information for an enzyme-inhibitor complex to gain further insights regarding the mechanism of hydrolysis of phosphatidylinositides by this PI-PLC.
PREPARATION AND STRUCTURAL STUDIES OF A NUMBER OF HETEROCYCLIC PHOSPHORANES
Denney, Donald B.,Denney, Dorothy Z.,Liu, Lun-Tsu
, p. 71 - 84 (2007/10/02)
A series monocyclic five-membered ring containing trivalent phosphorous compound with oxygen, nitrogen and sulfur bonded to phosphorous, in various combinations has been allowed to react with trifluoroethyl and 1,1,1,3,3,3-hexafluoroisopropyl benzenesulfenates.In some cases, pentacoordinated phosphorous compounds resulted.These materials have been studied by various NMR techniques.The same trivalent phosphorous compounds were allowed to react with 3,4-(bistrifluoromethyl)1,2,dithiete.In some cases phosphoranes were formed and they were also studied by NMR.
