Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Design and synthesis of a macrosphelide A-biotin chimera

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7127-7135
DOI: 10.1039/C4OB01028K, PaperHwayoung Yun, Jaehoon Sim, Hongchan An, Jeeyeon Lee, Hun Seok Lee, Young Kee Shin, Seung-Mann Paek, Young-Ger Suh
The rational design and synthesis of a biochemical probe of natural (+)-macrosphelide A, a potent cell-cell adhesion inhibitor, was completed to aid in the identification of its biological target.
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A large dipole moment to promote gelation for 4-nitrophenylacrylonitrile derivatives with gelation-induced emission enhancement properties

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7110-7118
DOI: 10.1039/C4OB00768A, PaperPengchong Xue, Boqi Yao, Yuan Zhang, Peng Chen, Kechang Li, Baijun Liu, Ran Lu
4-Nitrophenylacrylonitrile derivatives were gelator, but analogues without nitro group were not, indicating that the electron-withdrawing nitro moiety was important for gel formation. Moreover, the organogels exhibited fluorescence enhancement.
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Effect of conformational rigidity on the stereoselectivity of nucleophilic additions to five-membered ring bicyclic oxocarbenium ion intermediates

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7083-7091
DOI: 10.1039/C4OB01251H, PaperOlga Lavinda, Vi Tuong Tran, K. A. Woerpel
Nucleophilic substitution reactions of five-membered ring acetals bearing fused rings reveal that subtle changes in the structure of the fused ring can exert dramatic influences on selectivity.
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Expedient synthesis of an [small alpha]-S-(1[rightward arrow]6)-linked pentaglucosyl thiol

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7119-7126
DOI: 10.1039/C4OB01094A, PaperHuali Wang, Xiangming Zhu
An [small alpha]-S-(1[rightward arrow]6)-linked pentaglucosyl thiol (1) is synthesized via the longest linear sequence of eleven steps from an [small alpha]-glucosyl thiol (7).
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Ratiometric fluorescence chemosensor based on tyrosine derivatives for monitoring mercury ions in aqueous solutions

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7100-7109
DOI: 10.1039/C4OB01044B, PaperPonnaboina Thirupathi, Ponnaboina Saritha (nee Gudelli), Keun-Hyeung Lee
Ratiometric fluorescent chemosensors 1 and 2 were synthesized based on tyrosine amino acid derivatives with a pyrene fluorophore.
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Monitoring penetratin interactions with lipid membranes and cell internalization using a new hydration-sensitive fluorescent probe

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7036-7044
DOI: 10.1039/C4OB01242A, PaperOleksandr M. Zamotaiev, Viktoriia Y. Postupalenko, Volodymyr V. Shvadchak, Vasyl G. Pivovarenko, Andrey S. Klymchenko, Yves Mely
A new hydration-sensitive fluorescent label attached to the N-terminus of a cell-penetrating peptide allows visualization of the nanoscopic environment of its internalization pathway.
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Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (+/-)-epi-indolizidine 167B and 209D

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7026-7035
DOI: 10.1039/C4OB01130A, PaperAnil K. Saikia, Kiran Indukuri, Jagadish Das
A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (+/-)-epi-indolizidine 167B and 209D.
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Combinatorial synthesis of nicotine analogs using an Ugi 4-CR/cyclization-reduction strategy

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7068-7082
DOI: 10.1039/C4OB00767K, PaperLuis A. Polindara-Garcia, Alfredo Vazquez
A simple and convenient synthetic methodology to prepare nicotine derivatives is reported.
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Novel EDTA-ligands containing an integral perylene bisimide (PBI) core as an optical reporter unit

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7045-7058
DOI: 10.1039/C4OB01007H, PaperMario Marcia, Prabhpreet Singh, Frank Hauke, Michele Maggini, Andreas Hirsch
The synthesis, characterization and metal complexation of a new class of perylene bisimides (PBIs) as an integral part of ethylenediaminetetraacetic acid (EDTA) are reported.
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Control of reaction pathways in the photochemical reaction of a quinone with tetramethylethylene by metal binding

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,7004-7017
DOI: 10.1039/C4OB00659C, PaperHiroaki Yamamoto, Kei Ohkubo, Seiji Akimoto, Shunichi Fukuzumi, Akihiko Tsuda
Supramolecular photochemical reactions of a quinone derivative, bearing an oligoether sidearm, with tetramethylethylene occur upon noncovalent complexations with metal salts.
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Evaluation of 4-substituted styrenes as functional monomers for the synthesis of theophylline-specific molecularly imprinted polymers

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, 12,6994-7003
DOI: 10.1039/C4OB00517A, PaperHazit Zayas, Clovia I. Holdsworth, Michael C. Bowyer, Adam McCluskey
Six novel functional monomers (M1-M6) were examined for their ability to imprint theophylline (1). The best selectivity was observed with M2.
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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

26 August, 2014 - 19:54
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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Approaches to the total synthesis of chaetochalasin A

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01308E, PaperEric J. Thomas, Mark Willis
Chaetochalasin A is a complex natural product whose biosynthesis may involve two domino Diels-Alder reactions.
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CONFORMATIONALLY CONSTRAINED NUCLEOSIDE PHOSPHONIC ACIDS - POTENT INHIBITORS OF HUMAN MITOCHONDRIAL AND CYTOSOLIC 5'(3')-DEOXYNUCLEOTIDASES

24 August, 2014 - 19:17
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

24 August, 2014 - 19:17
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

24 August, 2014 - 19:17
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

24 August, 2014 - 19:17
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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Pyrazole-oxadiazole Conjugates: Synthesis, Antiproliferative Activity and Inhibition of Tubulin Polymerization

24 August, 2014 - 19:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01152J, PaperAhmed Kamal, Anver Basha Shaik, Sowjanya Polepalli, Santhosh Reddy Vangala, Bharath Kumar G, Soma Gupta, Nagabhushana Ananthamurthy, Rakesh K Mishra, Nishant Jainb, Venkata Siva Ramakrishna Kallaganti
A number of pyrazole-oxadiazole conjugates were synthesized and evaluated for their ability to function as antiproliferative agents on various human cancer cell lines. These conjugates comprise of pyrazole and oxadiazole...
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Rhodium-catalyzed olefination of aryl tetrazoles via direct C-H bond activation

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01440E, CommunicationLiang Wang, Wen Wu, Qun Chen, Ming-Yang He
Rh(III)-catalyzed direct olefination reaction via aromatic C-H bond activation is described using tetrazole as the directing group. This reaction provides a straightforward way for the synthesis of ortho-alkenyl aryl tetrazoles....
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Indole synthesis from N-allenyl-2-iodoanilines under mild conditions mediated by samarium(II) diiodide

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6812-6815
DOI: 10.1039/C4OB01164C, CommunicationHiroki Iwasaki, Kenji Suzuki, Mitsunari Yamane, Shohei Yoshida, Naoto Kojima, Minoru Ozeki, Masayuki Yamashita
A novel method for indole skeleton synthesis under mild conditions mediated by samarium(II) diiodide has been developed.
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