22381-54-0Relevant articles and documents
COMPOSITIONS AND METHODS FOR SYNTHESIS OF PHOSPHORYLATED MOLECULES
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, (2019/10/29)
The invention provides compositions and methods for synthesis of phosphorylated organic compounds, including nucleoside triphosphates.
Design, Synthesis, and Evaluation of 2-(arylsulfonyl)oxiranes as Cell-permeable Covalent Inhibitors of Protein Tyrosine Phosphatases
Dana, Dibyendu,Das, Tirtha K.,Kumar, Ish,Davalos, Anibal R.,Mark, Kevin J.,Ramai, Daryl,Chang, Emmanuel J.,Talele, Tanaji T.,Kumar, Sanjai
, p. 489 - 499 (2012/11/06)
A structure-based design approach has been applied to develop 2-(arylsulfonyl)oxiranes as potential covalent inhibitors of protein tyrosine phosphatases. A detailed kinetic analysis of inactivation by these covalent inhibitors reveals that this class of compounds inhibits a panel of protein tyrosine phosphatases in a time- and dose-dependent manner, consistent with the covalent modification of the enzyme active site. An inactivation experiment in the presence of sodium arsenate, a known competitive inhibitor of protein tyrosine phosphatase, indicated that these inhibitors were active site bound. This finding is consistent with the mass spectrometric analysis of the covalently modified protein tyrosine phosphatase enzyme. Additional experiments indicated that these compounds remained inert toward other classes of arylphosphate-hydrolyzing enzymes, and alkaline and acid phosphatases. Cell-based experiments with human A549 lung cancer cell lines indicated that 2-(phenylsulfonyl)oxirane (1) caused an increase in intracellular pTyr levels in a dose-dependent manner thereby suggesting its cell-permeable nature. Taken together, the newly identified 2-(arylsulfonyl)oxiranyl moiety could serve as a novel chemotype for the development of activity-based probes and therapeutic agents against protein tyrosine phosphatase superfamily of enzymes.
METHOD AND COMPOUNDS FOR RNA SYNTHESIS
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Page/Page column 17, (2010/11/27)
The 2-(4-tolylsulfonyl)ethoxymethyl (TEM) as a new 2'-OH protecting group is reported for the RNA synthesis on the solid support using the phosphoramidite chemistry. The usefulness of the 2'-0-TEM group is exemplified by the synthesis of 12 different oligo-RNAs of various sizes (14-38nt long). The stepwise coupling yield varied from 97 - 99 % with an optimized coupling time of 120s. Synthesis of all four pure phosphoramidite building blocks are also described. Two new reliable parameters, δc2' - δc3s and δn2' - δH3' have been suggested for the characterization of isomeric 2'-0-TEM and 3'-0-TEM as well as other isomeric mono 273 '-protected ribonucleoside derivatives. The most striking feature of this strategy is that the crude RNA prepared using our 2'-0-TEM strategy is sufficiently pure (>90 %) for molecular biology research without any additional purification step, thereby making oligo-RNAs easily available at a relatively low cost, saving both time and lab resources.
2-(4-Tolylsulfonyl)ethoxymethyl (TEM) - A new 2′-OH protecting group for solid-supported RNA synthesis
Zhou, Chuanzheng,Honcharenko, Dmytro,Chattopadhyaya, Jyoti
, p. 333 - 343 (2008/03/27)
The 2-(4-tolylsulfonyl)ethoxymethyl (TEM) as a new 2′-OH protecting group is reported for solid-supported RNA synthesis using phosphoramidite chemistry. The usefulness of the 2′-O-TEM group is exemplified by the synthesis of 12 different oligo-RNAs of var
A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
Dransfield, Paul J.,Dilley, Anja S.,Wang, Shaohui,Romo, Daniel
, p. 5223 - 5247 (2007/10/03)
Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine.
Process for producing [2-(arylsulfonyl) ethenyl] benzene derivatives
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, (2008/06/13)
The present invention provides a safer and more efficient process for producing [2-(arylsulfonyl)ethenyl]benzene derivatives of the formula (3): wherein R1, R2, R3 and R4 are the same or different and each independently represent a hydrogen, fluorine, or chlorine atom, a lower alkyl group, or the like, and two adjacent R3 and R4 may bond each other at their terminals to form a ring, which the process is characterized in that a 2-(arylsulfonyl)ethanol of formula (1): wherein R1 and R2 are as defined above, and an acid anhydride are reacted in the presence of a base, and the reaction liquid obtained is supplied to a reaction with an aromatic halide of formula (2): wherein X represents a chlorine, bromine, or iodine atom, and R3 and R4 are the same as defined above, in the presence of a palladium catalyst and a base.
Remote Participation during Photooxidation at Sulfur. Eidence for Sulfurane Intermediates
Clennan, E. L.,Yang, Kang
, p. 4477 - 4487 (2007/10/02)
The photooxidations of geminally substituted γ-hydroxy sulfides results in formation of unusual oxidative elimination products.Detailed spectral data and the independent synthesis of a close analogue provide compelling evidence for the structures of these
Regioselective ring opening of oxiranes catalysed by montmorillonite clay: A simple synthesis of β-hydroxy sulfones
Biswas,Bhattacharyya
, p. 569 - 573 (2007/10/02)
Oxiranes and sodium p-toluene sulfinate salt react smoothly in a regioselective manner in the presence of montmorillonite clay to furnish the corresponding β-hydroxy sulfones in good to excellent yield.
Novel 1H-Benzimidazol-4-ols with Potent 5-Lipoxygenase Inhibitory Activity
Buckle, Derek R.,Foster, Keith A.,Taylor, John F.,Tedder, John M.,Thody, Veronica E.,et al.
, p. 2216 - 2221 (2007/10/02)
The synthesis and structure-activity profile of 2-substituted benzimidazol-4-ols as inhibitors of cell-free RBL-1 5-lipoxygenase are discussed, and their potency is compared with that of the standard inhibitors phenidone, AA 861, BW 755C, and nordihydroguaiaretic acid.In contrast to the standard comounds, most did not inhibit the release of slow-reacting substance of anaphylaxis (SRS-A) in vivo when administered at 200 μM ip to rats subjected to peritoneal anaphylaxis, although five compounds containing a methoxylated benzyl group (compounds 36, 39, 42, and 43) or hydroxylated benzyl group (41) showed similar activity to that of phenidone, nordihydroguaiaretic acid, and AA 861.Of the many compounds tested, two, 5-tert-butyl-7-methyl-2-(trifluoromethyl)-1H-benzimidazol-4-ol (57) and 2-(4-methoxybenzyl)-7-methyl-1H-benzimidazol-4-ol (36), like dexamethasone, inhibited monocyte accumulation in a pleural exudate model of inflammation.Standard lipoxygenase inhibitors such as phenidone, BW 755C, and AA 861 were inactive in this system.
