Royal Society of Chemistry

A Lewis acid-mediated conformational switch

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01556H, PaperPeter Clarke Knipe, Hannah Lingard, Ian M Jones, Sam Thompson, Andrew D Hamilton
Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis...
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Neither azeotropic drying, nor base, nor other additives - a minimalist approach to 18F-labeling

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01336K, PaperRaphael Richarz, Philipp Krapf, Elizaveta Alexandrovna Urusova, Bernd Neumaier, Boris Dmitrievitch Zlatopolskiy
A novel, efficient, time-saving and reliable radiolabeling procedure via nucleophilic substitution with [18F]fluoride is described. Different radiolabeled aliphatic and aromatic compounds were prepared in high radiochemical yields simply by the...
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Origins of exo-Stereoselectivity of Norbornene in Hetero Diels-Alder Reactions

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01217H, PaperSesil Agopcan, Selami Ercan, Sule Erol, Ilknur Dogan, Viktorya Aviyente
In this study the exo selectivity in the hetero Diels-Alder reaction of atropisomeric 5-benzylidine-2-arylimino-3-aryl-thiazolidine-4-thiones with norbornene has been investigated with computational tools. Taking into account the M/P chiral character of...
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Non-isoprenoid Polyene Natural Products - Structures and Synthetic Strategies

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01337A, Review ArticleAndrew Whiting, Katrina Madden, Fathia Mosa
This review provides insight into the variety of structures and biological activities found in the non-isoprenoid family of polyene natural products and examines the strategies and synthetic methods applied for...
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Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01358A, PaperXuan Zhao, Tian-Ze Li, Jing-Ying Qian, Feng Sha, Xin-Yan Wu
The first enantioselective aza-Morita-Baylis-Hillman reaction of acrylates with ketimines derived from isatins has been developed. With 2 mol% of chiral bifunctional phosphine-squaramide 4e, optically active 3-substituted-3-amino-2-oxindoles were obtained in excellent...
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Iron-catalyzed direct difunctionalization of alkenes with dioxygen and sulfinic acids: a highly efficient and green approach to [small beta]-ketosulfones

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01369G, CommunicationHua Wang, Wei Wei, Jiangwei Wen, Daoshan Yang, Min Wu, Jinmao You
A novel iron-catalyzed direct difunctionalization of alkenes with sulfinic acids and dioxygen for the synthesis of [small beta]-ketosulfones has been developed under mild conditions. The present protocol, which utilizes inexpensive iron...
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Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01063A, Review ArticleAlexander Drohat, Atanu Maiti
DNA glycosylases remove damaged or enzymatically modified nucleobases from DNA, thereby initiating the base excision repair (BER) pathway, which is found in all forms of life. These ubiquitous enzymes promote...
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A Small Synthetic Molecule Forms Selective Potassium Channels to Regulate Cell Membrane Potential and Blood Vessel Tone

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01420K, PaperD Yang, Hui-Yan Zha, Bing Shen, Kwok-Hei Yau, Shing-To Li, Xiao-Qiang Yao
In living cell membranes, K+ permeability is higher than other ions such as Na+ and Cl- owing to abundantly expressed K+ channels. Polarized membrane potential is mainly established by K+...
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Enantioselective copper catalysed C-H insertion reaction of 2-sulfonyl-2-diazoacetamides to form [gamma]-lactams.

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01430H, PaperAnita R Maguire, Leslie Ann Clarke, Aoife Ring, Alan Ford, Abhijeet Shekhar Sinha, Simon Lawrence
The first examples of asymmetric copper-catalysed intramolecular C-H insertion reactions of 2-sulfonyl-2-diazoacetamides are described; trans -lactams with up to 82%ee are achieved with the CuCl2-bisoxazoline-NaBARF catalyst system. The reactions generally...
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Nitroso Diels-Alder (NDA) reaction as an efficient tool for the functionalization of diene-containing natural products

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01033G, Review ArticleSerena Carosso, Marvin J. Miller
This review describes the use of nitroso Diels-Alder reactions for the functionalization of complex diene-containing natural products in order to generate libraries of compounds with potential biological activity.
To cite this article before page numbers are assigned, use the DOI form of citation above.
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Nitroxide-labeled pyrimidines for non-covalent spin-labeling of abasic sites in DNA and RNA duplexes

Org. and Biomol. Chem. - 18 August, 2014 - 17:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01095G, PaperSandip A. Shelke, Gunnar B. Sandholt, Snorri Th. Sigurdsson
Of ten new pyrimidine-derived nitroxide spin labels, an N1-ethylamino triazole-linked uracil derivative binds fully to both DNA and RNA duplexes containing an abasic site, as determined by CW-EPR.
To cite this article before page numbers are assigned, use the DOI form of citation above.
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Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01436G, CommunicationRadomir Nikola Saicic, Radomir Matovic, Filip Bihelovic, Maja Gruden-Pavlovic
Total synthesis of desmethylabyssomicin C analogue 1 was accomplished using diastereotopos-selective ring closing metathesis and Nozaki-Hiyama-Kishi cyclization as the key steps. The synthetic analogue retained the antibacterial activity against Methicillin-resistant...
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Adaptable synthesis of C-lactosyl glycoclusters and their binding properties with galectin-3

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01374C, PaperWang Yao, Mengjie Xia, Xiangbao Meng, Qing Li, Zhongjun Li
We report here the syntheses of mono- to tetravalent glycoclusters containing 1-methylene-C-[small beta]-lactose. The 1-methylene-C-[small beta]-lactose moiety has been synthesized from octa-acetyl-[small beta]-lactose using the key carbonyl insertion reaction and linked to a...
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Synthesis and Evaluation of Photoresponsive Quencher for Fluorescent Hybridization Probes

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01185F, PaperMarina Kovaliov, Chaim Wachtel, Eylon Yavin, Bilha Fischer
This is an Accepted Manuscript, which has been through the RSC Publishing peer review process and has been accepted for publication. Accepted manuscripts are published online shortly after acceptance. This version of the article will be replaced by the fully edited, formatted and proof read Advance Article as soon as this is available.
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Design Strategy for Small Molecule-based Targeted MRI Contrast Agents: Application for Detection of Atherosclerotic Plaques

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01270D, PaperShimpei Iwaki, Kazuya Hokamura, Mikako Ogawa, Yasuo Takehara, Yasuaki Muramatsu, Takehiro Yamane, Kazuhisa Hirabayashi, Yuji Morimoto, Kohsuke Hagisawa, Kazuhide Nakahara, Tomoko Mineno, Takuya Terai, Toru Komatsu, Tasuku Ueno, Keita Tamura, Yusuke Adachi, Yasunobu Hirata, Makoto Arita, H. Arai, Kazuo Umemura, Tetsuo Nagano, kenjiro Hanaoka
Gadolinium(III) ion (Gd3+) complexes are widely used as contrast agents in magnetic resonance imaging (MRI), and many attempts have been made to couple them to sensor moieties in order to...
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Molecular Iodine-Mediated Reaction of 2-(2-phenylethynyl)-Morita-Baylis-Hillman Adducts: An Easy Access to Naphthyl ketones and Iodo-Substituted Isochromenes

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00938J, PaperChing-Fa Yao, Janreddy Donala, Veerababurao Kavala, Trimurtulu Kotipalli, Rajawinslin. R. R, Chun-Wei Kuo, Wen-Chang Huang
The molecular iodine-promoted reaction of 2-(2-phenylethynyl)-Morita-Baylis-Hillman adducts is reported. In the presence of I2, naphthyl ketone derivatives are produced, whereas, in the presence of I2/K3PO4, iodo-substituted isochromenes derivatives are produced.
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CONFORMATIONALLY CONSTRAINED NUCLEOSIDE PHOSPHONIC ACIDS - POTENT INHIBITORS OF HUMAN MITOCHONDRIAL AND CYTOSOLIC 5'(3')-DEOXYNUCLEOTIDASES

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01332H, PaperOndrej Simak, Petr Pachl, Milan Fabry, Milos Budesinsky, Tomas Jandusik, Ales Hnizda, Radka Sklenickova, Magdalena Petrova, Vaclav Veverka, Pavlina Rezacova, Jiri Brynda, Ivan Rosenberg
This work describes novel in vitro inhibitors of human mitochondrial (mdN) and cytosolic (cdN) 5'(3')-deoxynucleotidases. We designed a series of derivatives of the lead compound (S)-1-[2-deoxy-3,5-O-(phosphonobenzylidene)-[small beta]-D-threo-pentofuranosyl]thymine bearing various substituents in...
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Synthesis of Fluorescent 2,3,5,6-Tetraalkynylpyridines by Site-Selective Sonogashira-Reactions of 2,3,5,6-Tetrachloropyridines

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01292E, PaperPeter Ehlers, Andranik Petrosyan, Antje Neubauer, Timo Broese, Stefan Lochbrunner, Tariel Ghochikyan, Ashot Saghyan, Peter Langer
4-Substituted 2,3,5,6-tetraalkynylpyridines were prepared by tetra-fold Sonogashira reactions of the corresponding 2,3,5,6-tetrachloropyridines. 2,6-Dialkynyl-3,5-dichloropyridines were prepared by site-selective Sonogashira reactions from various 4-unsubstituted and 4-substituted tetrachloropyridines. Subsequent two-fold Sonogashira reactions of...
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Asymmetric Michael addition of ketones to nitroolefins: Pyrrolidinyl-oxazole-carboxamides as new efficient organocatalysts

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01223B, PaperAhmed Kamal, Sathish Manda, vunnam srinivasulu, Chetna Jadala, Chandra Shekar Kunta, Shalini Nekkanti, Yellaiah Tangella, Nagula Shankaraiah
Chiral pyrrolidinyl-oxazole-carboxamides were synthesized and used as efficient new organocatalysts for the asymmetric Michael addition of ketones with nitroalkenes under solvent-free conditions. Gratifyingly, the corresponding Michael adducts were obtained in...
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Multiple optical properties of naphthoquinone pigment: 2-methyl-3-(hydroxyphenylthio)-1,4-naphthalenedione

Org. and Biomol. Chem. - 18 August, 2014 - 17:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01058B, PaperHirotaka Akiyama, Takafumi Inoue, Nobuo Tajima, Reiko Kuroda, Yoshitane IMAI
Naphthoquinone pigments 2-methyl-3-(4- or 2-hydroxyphenylthio)-1,4-naphthalenedione show characteristic optical properties in solution and in the solid state. The position of the OH group in the pigment leads to varied optical properties,...
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