Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Removal of amino groups from anilines through diazonium salt-based reactions

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,6965-6971
DOI: 10.1039/C4OB01286K, Review ArticleLinman He, Guanyinsheng Qiu, Yueqiu Gao, Jie Wu
In situ generation of diazonium salts from anilines represents an efficient and practical pathway, leading to a series of useful structures. The amino group in anilines acts as a formal leaving group in various coupling reactions.
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An easy access to [small alpha]-aryl substituted [gamma]-ketophosphonates: Lewis acid mediated reactions of 1,3-diketones with [small alpha]-hydroxyphosphonates and tandem regioselective C-C bond cleavage

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, 12,7140-7149
DOI: 10.1039/C4OB01091D, PaperGangaram Pallikonda, Manab Chakravarty, Manoj K. Sahoo
The [small alpha]-aryl substituted (+/-)-[gamma]-ketophosphonates are produced by Lewis acid mediated reactions of [small alpha]-hydroxyphosphonates with 1,3-diketones.
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Design and synthesis of a macrosphelide A-biotin chimera

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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

20 August, 2014 - 18:17

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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Multiple optical properties of naphthoquinone pigment: 2-methyl-3-(hydroxyphenylthio)-1,4-naphthalenedione

20 August, 2014 - 18:17
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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Recognition of double-stranded DNA using energetically activated duplexes with interstrand zippers of 1-, 2- or 4-pyrenyl-functionalized O2'-alkylated RNA monomers

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01183J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Saswata Karmakar, Andreas S Madsen, Dale Guenther, Bradley C Gibbons, Patrick Jerzy Hrdlicka
Despite advances with triplex-forming oligonucleotides, peptide nucleic acids, polyamides and - more recently - engineered proteins, there remains an urgent need for synthetic ligands that enable specific recognition of double-stranded...
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Pyrazole-oxadiazole Conjugates: Synthesis, Antiproliferative Activity and Inhibition of Tubulin Polymerization

20 August, 2014 - 18:17
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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Thiomyristoyl Peptides as Cell-Permeable Sirt6 Inhibitors

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB00860J, CommunicationBin He, Jing Hu, Xiaoyu Zhang, Hening Lin
Sirtuins regulate a variety of biological pathways and inhibitors of sirtuins have been actively pursued as tool compounds to study sirtuin biology and as potential therapeutics. Here we demonstrate that...
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Generalized access to fluorinated [small beta]-keto amino compounds through asymmetric additions of [small alpha],[small alpha]-difluoroenolates to CF3-sulfinylimine

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01575D, PaperChen Xie, Lingmin Wu, Haibo Mei, Vadim A Soloshonok, Jianlin Han, Yi Pan
CF3-containing chiral imines readily react with [small alpha],[small alpha]-difluoroenolates affording a novel type of -keto-amino compounds featuring R-CO-CF2-CH(NH2)-CF3 moiety. The reactions feature exceptional generality allowing preparation of various aromatic, hetero-aromatic and aliphatic...
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AcOH-mediated dichloroimination of indoles using chloramine-B: A facile access to 2,3-functionalized indolines

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01179A, CommunicationXiaozu Liu, Qinghong Hu, Zeli Yuan, Peijun Liu
A new and mild method for the efficient synthesis of 3,3-dichloro-2-sulfonyliminoindolines via AcOH-mediated dichloroimination of indoles using chloramineB is presented. Application of this method to the efficient construction of pyrrolidinoindoles...
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Palladium-catalyzed ortho-Acylation of 2-Benzyl-1,2,3-Triazoles with Aldehydes

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01406E, CommunicationQingshan Tian, Ping He, Chunxiang Kuang
A palladium-catalyzed ortho-acylation of 2-benzyl-1,2,3-triazoles with aldehydes as acyl source is developed. A wide variety of ketones containing 1,2,3-triazoles were obtained in good to excellent yields. This methodology provides a...
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