Royal Society of Chemistry

Pd(II)-Catalyzed C-H Arylation of Aryl and Benzyl Weinreb Amides

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02039A, CommunicationXi-Sheng Wang, Yan Wang, Kai Zhou, Quan Lan
The first example of palladium-catalyzed ortho-C-H arylation of aryl and benzyl Weinreb amides was developed, in which HOTf was used as a key promoter. This method exhibits good functional groups...
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Naphthalene Diimides as Red Fluorescent pH Sensors for Functional Cells Imaging

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02054E, PaperFilippo Doria, Marco Folini, Vincenzo Grande, Graziella Cimino-Reale, Nadia Zaffaroni, Mauro Freccero
A small library of hydrosoluble naphthalene diimides (NDIs) was designed and synthesized, as cell permeable pH "turned-on" fluorescent sensors, for cellular applications. The NDIs exhibit a non-emitting twisted intramolecular charge...
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Synthesis and evaluation of protein arginine N-methyltransferase inhibitors designed to simultaneously occupy both substrate binding sites

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01734J, PaperMatthijs van Haren, Linda Quarles van Ufford, Ed E. Moret, Nathaniel I. Martin
The protein arginine N-methyltransferases (PRMTs) are a family of enzymes that function by specifically transferring a methyl group from the cofactor S-adenosyl-L-methionine (AdoMet) to the guanidine group of arginine residues...
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1,1-Alkenylboration of diarylphosphino-enynes: convenient synthetic entry to vicinal P/B Lewis pairs at extended conjugated [small pi]-frameworks

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02134G, PaperGerald Kehr, G Erker, Constantin Gabriel Daniliuc, Guo-Qiang Chen
Alkenylboranes R-CH=CH-B(C6F5)2 undergo carbon-carbon coupling by means of 1,1-alkenylboration with diarylphosphino-enynes to give substituted conjugated hexatriene derivatives that bear a vicinal pair of B(C6F5)2 Lewis acid and PAr2 Lewis base...
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Development of a novel fluorescence probe capable of assessing the cytoplasmic entry of siderophore-based conjugates

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01810A, CommunicationHyeon Seok Kim, Woon Young Song, Hak Joong Kim
A novel fluorescence probe capable of assessing the cytoplasmic entry of siderophore-based conjugates was synthesized and evaluated by photochemical characterization and cell-based assays. The specific responsiveness to the cytoplasmic entry...
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A Facile Approach to Tryptophan Derivatives for the Total Synthesis of Argyrin Analogues

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02107J, CommunicationChou-Hsiung Chen, Sivaneswary Genapathy, Peter M Fischer, Weng Chan
A facile route has been established for the synthesis of indole-substituted (S)-tryptophans from corresponding indoles, which utilizes a chiral auxiliary-facilitated Strecker amino acid synthesis strategy. The chiral auxiliary reagents evaluated...
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Amino acid-linked porphyrin-nitroimidazole antibiotics targeting Porphyromonas gingivalis

Org. and Biomol. Chem. - 7 hours 38 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01841A, PaperSimon A. Dingsdag, Benjamin C-M. Yap, Neil Hunter, Maxwell J. Crossley
Amino acid-linked porphyrin-nitroimidazole adducts, as potent as metronidazole, are highly selective for Porphyromonas gingivalis.
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A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01977F, PaperRaveendra Babu Kaki, Faiz Ahmed Khan
An efficient acid induced rearrangement of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl system leading to substituted indenones is reported. This domino reaction involves dehydration, olefin isomerization, ketal hydrolysis, [3,3]-sigmatropic rearrangement and dehydrohalogenation. The resultant vicinal...
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Synthesis of coenzyme A thioesters using methyl acyl phosphates in an aqueous medium

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02079K, CommunicationMohan Pal, Stephen L. Bearne
Regioselective S-acylation of coenzyme A (CoA) is achieved under aqueous conditions using various aliphatic and aromatic carboxylic acids activated as their methyl acyl phosphate monoesters. Unlike many hydrophobic activating groups,...
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Late-Stage Diversification of Biologically Active Pyridazinones via Direct C-H Functionalization Strategy

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02061H, PaperWei Li, Zhoulong Fan, Kaijun Geng, Youjun Xu, Ao Zhang
Divergent C-H functionalization reactions (arylation, carboxylation, olefination, thiolation, acetoxylation, halogenation, naphthylation) using a pyridazinone moiety as an internal directing group were successfully established. This approach offers a late-stage, ortho-selective diversification...
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Sc(OTf)3-mediated 1,3-dipolar cycloaddition-ring cleavage-rearrangement: a highly stereoselective access to Z-[small beta]-enaminonitriles

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01801J, PaperYing-chun Wang, Yu-Yang Xie, Xian-chun Tan, Hengshan Wang, Ying-ming Pan
A novel and highly stereoselective synthesis of Z-[small beta]-enaminonitriles from azides and [small alpha],[small beta]-unsaturated nitriles is reported. The reaction proceeds via a 1,3-dipolar cycloaddition-ring cleavage-rearrangement cascade mediated by catalytic amount of Sc(OTf)3....
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The synthesis of 3-hydroxy-2,4,8-trimethyldec-8-enolides and an approach to 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01792G, PaperRosario Hern�ndez- Gal�n, Jose Manuel Botubol, Maria Jesus Duran-Pena, Antonio Jose Macias-Sanchez, I. G. Collado, James R Hanson
The synthesis of several derivatives of 3-hydroxy-2,4,8-trimethyldec-8-enolide and attempts at the synthesis of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1), a structure which has been assigned to a metabolite of the phytopathogenic fungus, Botrytis cinerea,...
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Trifluoromethanesulfonyloxy-Group-Directed Regioselective (3+2) Cycloadditions of Benzynes for the Synthesis of Functionalized Benzo-Fused Heterocycles

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01627K, PaperTakashi Ikawa, Hideki Kaneko, Shigeaki Masuda, Erika Ishitsubo, Hiroaki TOKIWA, shuji akai
Highly regioselective (3+2) cycloadditions of (trifluoromethanesulfonyloxy)benzynes [(triflyloxy)benzynes] with 1,3-dipoles followed by cross-coupling reactions provided multisubstituted benzo-fused heterocycles. The triflyloxy group at the 3-position of benzynes, and even that at the...
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Ametantrone-based compounds as potential regulators of Tau pre-mRNA alternative splicing

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01925C, PaperGerard Artigas, Paula Lopez-Senin, Carlos Gonzalez, Nuria Escaja, Vicente Marchan
Tau pre-mRNA contains a stem-loop structure involved in the regulation of the alternative splicing of tau protein. We describe here a new family of Tau RNA ligands selected by a...
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Anion carrier formation by calix[4]arene-bis-hydroxymethylphosphonic acid in bilayer membranes

Org. and Biomol. Chem. - 7 hours 38 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01886A, PaperOleg Ya. Shatursky, Ludmila A. Kasatkina, Roman V. Rodik, Sergiy O. Cherenok, Alexander A. Shkrabak, Tatiana O. Veklich, Tatiana A. Borisova, Sergyi O. Kosterin, Vitaly I. Kalchenko
Calix[4]arene C-99-mediated ionic transport follows mobile carrier mode of facilitated diffusion (relative permeability PCl-/PK+ [similar] 3) with the passage of 20 ions per second.
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Novel Synthesis of 5-methyl-5,10-dihydroindolo[3,2-b]indoles by Pd-catalyzed C-C and two-fold C-N coupling reactions

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01723D, PaperTran Quang Hung, Soren Hancker, Alexander Villinger, Stefan Lochbrunner, Tuan T Dang, Aleksey Friedrich, Wolfgang Breitsprecher, Peter Langer
A series of 5,10-dihydroindolo[3,2-b]indoles was successfully prepared by an efficient two-step strategy based on site-selective Pd-catalyzed cross-coupling reaction with N-methyl-2,3-dibromoindole and subsequent cyclization by two-fold Pd-catalyzed C-N coupling with amines....
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Indium-Catalyzed Intramolecular Hydroarylation of Aryl Propargyl Ethers

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02033B, PaperLorena Alonso-Maranon, M. Montserrat Martinez, Luis Sarandeses, Jose Perez Sestelo
Indium(III) halides catalyze efficiently the intramolecular hydroarylation (IMHA) of aryl propargyl ethers. The reaction proceeds regioselectively with a variety of electron-rich and electron-deficient benzenes and with terminal and internal alkynes...
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Visible light-mediated dehydrogenative [small beta]-arylsulfonylation of tertiary aliphatic amines with arylsulfonyl chlorides

Org. and Biomol. Chem. - 7 hours 38 min ago

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01713G, CommunicationMin Chen, Zhi-Tang Huang, Qi-Yu Zheng
[small beta]-Arylsulfonyl enamines were synthesized exclusively in E-form by the reaction of tertiary aliphatic amines with arylsulfonyl chlorides under visible light open to air with 1 mol% Ru(bpy)3(PF6)2 as the photosensor.
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Evaluation of a Focused Virtual Library of Heterobifunctional Ligands for Clostridium difficile Toxins

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01838A, PaperDavid R Bundle, Carlos A Sanhueza, Jonathan Cartmell, Amr El-Hawiet, Adam Szpacenko, Elena Kitova, Rambod Daneshfar, John Klassen, Luiz Eugenio, Kenneth Ng, Pavel I Kitov, Dean E Lang
A focused library of virtual heterobifunctional ligands was generated in silico and a set of ligands with recombined fragments was synthesized and evaluated for binding to Clostridium difficile toxins. The...
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Preparation of Cycloheptane Ring by Nucleophilic Cyclopropanation of 1,2-Diketones with Bis(iodozincio)methane

Org. and Biomol. Chem. - 7 hours 38 min ago
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01474J, PaperSeijiro Matsubara, Ryosuke Haraguchi, Yoshiaki Takada
We used a microflow system to study the nucleophilic cyclopropanation of hexa-1,5-diene-3,4-diones with bis(iodozincio)methane. This reaction afforded the zinc alkoxides of cis-dialkenylcylopropane-1,2-diols stereoselectively. The subsequent oxy-Cope rearrangement of cis-dialkenylcylopropane-1,2-diols afforded...
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