Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Synthesis, characterization and biological evaluation of carboranylmethylbenzo[b]acridones as novel agents for boron neutron capture therapy

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5201-5211
DOI: 10.1039/C4OB00644E, PaperA. Filipa F. da Silva, Raquel S. G. R. Seixas, Artur M. S. Silva, Joana Coimbra, Ana C. Fernandes, Joana P. Santos, Antonio Matos, Jose Rino, Isabel Santos, Fernanda Marques
Acridone derivatives bearing carboranyl moieties as fluorescent probes for boron neutron capture therapy (BNCT) of the glioblastoma.
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Multicomponent reaction for the first synthesis of 2,2-dialkyl- and 2-alkyl-2-aralkyl-5,6-diaryl-2H-1,3-thiazines as scaffolds for various 3,4-dihydro-2H-1,3-thiazine derivatives

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5168-5181
DOI: 10.1039/C4OB00866A, PaperFabian Brockmeyer, Robin Schoemaker, Marc Schmidtmann, Jurgen Martens
2H-1,3-thiazines, prepared via a novel and efficient multicomponent reaction, can be used as scaffolds for the synthesis of diverse 3,4-dihydro-2H-1,3-thiazines.
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Methylthiodeoxynivalenol (MTD): insight into the chemistry, structure and toxicity of thia-Michael adducts of trichothecenes

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5144-5150
DOI: 10.1039/C4OB00458B, PaperPhilipp Fruhmann, Theresa Weigl-Pollack, Hannes Mikula, Gerlinde Wiesenberger, Gerhard Adam, Elisabeth Varga, Franz Berthiller, Rudolf Krska, Christian Hametner, Johannes Frohlich
Synthesis and investigation of MTD revealed characteristic hemiketalisation and partial detoxification as effects of thia-Michael addition to type B trichothecenes.
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Mercuration of thiacalix[4]arenes in the cone and 1,3-alternate conformations

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5136-5143
DOI: 10.1039/C4OB00799A, PaperF. Botha, S. Bohm, H. Dvorakova, V. Eigner, P. Lhotak
A monomercuration reaction of thiacalix[4]arenes immobilized in the cone or 1,3-alternate conformations gave a mixture of two regioisomers (meta and para) in approx. 4 : 1 and 2 : 1 ratios, respectively.
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Outstanding effects on antithrombin activity of modified TBA diastereomers containing an optically pure acyclic nucleotide analogue

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5235-5242
DOI: 10.1039/C4OB00149D, PaperM. Scuotto, M. Persico, M. Bucci, V. Vellecco, N. Borbone, E. Morelli, G. Oliviero, E. Novellino, G. Piccialli, G. Cirino, M. Varra, C. Fattorusso, L. Mayol
Optically pure modified acyclic nucleosides offer unique advantages in exploring the effect on thrombin inhibition of single residue modifications at key positions of TBA.
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Polyamine modification by acrolein exclusively produces 1,5-diazacyclooctanes: a previously unrecognized mechanism for acrolein-mediated oxidative stress

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5151-5157
DOI: 10.1039/C4OB00761A, PaperAyumi Tsutsui, Rie Imamaki, Shinobu Kitazume, Shinya Hanashima, Yoshiki Yamaguchi, Masato Kaneda, Shinya Oishi, Nobutaka Fujii, Almira Kurbangalieva, Naoyuki Taniguchi, Katsunori Tanaka
Polyamines were found to react with acrolein to produce 1,5-diazacyclooctane.
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A colorimetric and ratiometric fluorescent probe for the imaging of endogenous hydrogen sulphide in living cells and sulphide determination in mouse hippocampus

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5115-5125
DOI: 10.1039/C4OB00285G, PaperLing Zhang, Sai Li, Mei Hong, Yuqing Xu, Shuaishuai Wang, Yi Liu, Yong Qian, Jing Zhao
A naphthalimide-azide based colorimetric and ratiometric fluorescent probe has been developed for the selective and sensitive detection of hydrogen sulphide.
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Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5108-5114
DOI: 10.1039/C4OB00398E, PaperBrian M. Muller, Jesse Mai, Reid A. Yocum, Marc J. Adler
The impact of substitution on a novel colorimetric dynamic covalent switching scaffold was investigated using UV/Vis and NMR spectroscopy.
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An ESIPT fluorescent probe sensitive to protein [small alpha]-helix structures

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5250-5259
DOI: 10.1039/C4OB00405A, PaperNan Jiang, Chanli Yang, Xiongwei Dong, Xianglang Sun, Dan Zhang, Changlin Liu
A benzazole derivative, 1, was observed to undergo the excited-state intramolecular proton transfer (ESIPT) process with [small alpha]-helical proteins. The cell images showed a difference in the staining of normal and cancerous prostate cells by 1, which might be due to the different membrane protein levels.
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Pd-catalyzed carbonylation for the construction of tertiary and quaternary carbon centers with sp3 carbon partners

1 July, 2014 - 04:17

Org. Biomol. Chem., 2014, 12,5243-5249
DOI: 10.1039/C4OB00568F, PaperWei Lu, Yang Li, Chao Wang, Dong Xue, Jian-Gang Chen, Jianliang Xiao
The first examples of a Pd-catalyzed carbonylation of aryl boronic acids with sp3 carbon partners are presented.
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Multivalent agents containing 1-substituted 2,3,4-trihydroxyphenyl moieties as novel synthetic polyphenols directed against HIV-1

29 June, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,5278-5294
DOI: 10.1039/C4OB00445K, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Aida Flores, Maria Jose Camarasa, Maria Jesus Perez-Perez, Ana San-Felix, Jan Balzarini, Ernesto Quesada
A series of synthetic polyphenols inspired by the multivalent architecture of naturally-occurring hydrolysable tannins exhibited selective inhibitory activity against HIV-1.
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Unusual truncation of N-acylated peptoids under acidic conditions

29 June, 2014 - 03:54

Org. Biomol. Chem., 2014, 12,5222-5226
DOI: 10.1039/C3OB42572J, PaperSoomin Kim, Goutam Biswas, Shinae Park, Arim Kim, Hyunjung Park, Eunsook Park, Jeongmi Kim, Yong-Uk Kwon
Systematic studies on the unusual truncation of N-acylated peptoids were carried out to examine the electronic effects of acyl groups, and thus to control the formation of deletion sequences based on a plausible mechanism.
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Fluoroacetate biosynthesis from the marine-derived bacterium Streptomyces xinghaiensis NRRL B-24674

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4828-4831
DOI: 10.1039/C4OB00970C, CommunicationSheng Huang, Long Ma, Ming Him Tong, Yi Yu, David O'Hagan, Hai Deng
Streptomyces xinghaiensis is the first fluorometabolite producing microorganism identified from the marine environment.
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Halide selective anion recognition by an amide-triazolium axle containing [2]rotaxane

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4924-4931
DOI: 10.1039/C4OB00801D, PaperNicholas G. White, Ana R. Colaco, Igor Marques, Vitor Felix, Paul D. Beer
A [2]rotaxane incorporating the novel 3-amido-phenyl-triazolium motif exhibits unusually high selectivity for halide anions over larger more basic oxoanions. Computational studies offer insight into this selectivity preference.
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[2]Pseudorotaxane formation between rigid Y-shaped 2,4,5-triphenylimidazolium axles and [24]crown-8 ether wheels

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4824-4827
DOI: 10.1039/C4OB00975D, CommunicationNasim Farahani, Kelong Zhu, Nadim Noujeim, Stephen J. Loeb
A new templating motif for the formation of [2]pseudorotaxanes is described in which rigid, Y-shaped axles with an imidazolium core and aromatic substituents at the 2-, 4- and 5-positions interact with [24]crown-8 ether wheels ([24]crown-8 and dibenzo[24]crown-8).
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Dual responsive supramolecular amphiphiles: guest molecules dictate the architecture of pyridinium-tailored anthracene assemblies

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4820-4823
DOI: 10.1039/C4OB00936C, CommunicationJun Hu, Peiyi Wang, Yuan Lin, Song Yang, Baoan Song, Qian Wang
By introducing an electron-deficient guest molecule and a counter anion, the assembly morphology of 1-[11-(2-anthracenylmethoxy)-11-oxoundecyl]pyridinium bromide (2-AP) was transformed to microsheets and nanofibers from microtubes, respectively.
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Synthesis of DIBAC analogues with excellent SPAAC rate constants

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,5031-5037
DOI: 10.1039/C4OB00694A, PaperMarjoke F. Debets, Jasper S. Prins, Donny Merkx, Sander S. van Berkel, Floris L. van Delft, Jan C. M. van Hest, Floris P. J. T. Rutjes
Four new DIBAC analogues showed excellent SPAAC rate constants making them comparable to the fastest cyclooctynes currently known.
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Rare Streptomyces sp. polyketides as modulators of K-Ras localisation

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4872-4878
DOI: 10.1039/C4OB00745J, PaperAngela A. Salim, Xue Xiao, Kwang-Jin Cho, Andrew M. Piggott, Ernest Lacey, John F. Hancock, Robert J. Capon
A rare class of oxanthromicin polyketides was isolated from a soil-derived Streptomyces sp. SAR-investigation showed that selected analogues can induce significant K-Ras plasma membrane mislocalisation and can synergise the K-Ras plasma membrane mislocalisation properties of staurosporine.
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A total synthesis of (+)-negamycin through isoxazolidine allylation

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4879-4884
DOI: 10.1039/C4OB00537F, PaperRoderick W. Bates, Rab'iah Nisha Khanizeman, Hajime Hirao, Yu Shan Tay, Patcharaporn Sae-Lao
The [small beta]-amino acid antibiotic (+)-negamycin has been synthesised in ten steps from epichlorohydrin via Sakurai allylation of an isoxazolidine intermediate.
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Cerium(III)-catalyzed cascade cyclization: an efficient approach to functionalized pyrrolo[1,2-a]quinolines

25 June, 2014 - 02:54

Org. Biomol. Chem., 2014, 12,4837-4840
DOI: 10.1039/C4OB00708E, CommunicationChengtao Feng, Yizhe Yan, Zhenglei Zhang, Kun Xu, Zhiyong Wang
A general and practical route to the synthesis of multisubstituted pyrrolo[1,2-a]quinolines has been described from 2-alkylazaarenes and nitroolefins using cerium chloride as a catalyst via a tandem Michael addition, cyclization and aromatization.
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