Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Pseudo-cyclic structures of mono- and di-azaderivatives of malondialdehydes. Synthesis and conformational disentanglement by computational analyses

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8997-9010
DOI: 10.1039/C4OB01507J, PaperMaria P. Romero-Fernandez, Martin Avalos, Reyes Babiano, Pedro Cintas, Jose L. Jimenez, Mark E. Light, Juan C. Palacios
Aminoacroleins and vinamidines are structures featuring H-bonding and complex conformational and tautomeric equilibria, which have been dissected by computation.
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Synthesis of functionalized fulvenes: [3 + 2] annulation of ethyl [small alpha]-chlorocyclopropaneformates with 1,3-dicarbonyl compounds

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8828-8831
DOI: 10.1039/C4OB01973C, CommunicationYuequan Zhu, Min Zhang, Hongling Yuan, Yuefa Gong
An efficient method is reported to produce acidic multi-substituted fulvenes at high yields (up to 94%) through the base-promoted [3 + 2] annulation reaction of ethyl [small alpha]-chlorocyclopropaneformates with 1,3-dicarbonyl compounds.
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Approaches to design non-covalent inhibitors for human granzyme B (hGrB)

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8952-8965
DOI: 10.1039/C4OB01874E, PaperMi-Sun Kim, Lauriane A. Buisson, Dean A. Heathcote, Haipeng Hu, D. Christopher Braddock, Anthony G. M. Barrett, Philip G. Ashton-Rickardt, James P. Snyder
A structure-based design campaign for non-covalent small molecule inhibitors of hGrB was carried out by virtual screening employing three constraints and probe site-mapping with FTMAP to identify ligand "hot spots".
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Chemical and biological evaluation of unusual sugars, [small alpha]-aculosides, as novel Michael acceptors

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8832-8835
DOI: 10.1039/C4OB01877J, CommunicationHiromasa Ikeda, Erika Kaneko, Shunsuke Okuzawa, Daisuke Takahashi, Kazunobu Toshima
Unusual sugars, [small alpha]-aculosides, were found to be novel and selective Michael acceptors to a thiol function of cysteine residues of proteins in living cells.
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A straightforward modification in the thrombin binding aptamer improving the stability, affinity to thrombin and nuclease resistance

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8840-8843
DOI: 10.1039/C4OB01475H, CommunicationVeronica Esposito, Maria Scuotto, Antonella Capuozzo, Rita Santamaria, Michela Varra, Luciano Mayol, Antonella Virgilio, Aldo Galeone
Introduction of inversion of polarity sites at the 5[prime or minute]- and/or 3[prime or minute]-end in the thrombin binding aptamer is a simple modification able to improve, at the same time, thermal stability, affinity to thrombin and nuclease resistance.
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The design, synthesis and biological evaluation of novel thiamin diphosphate analog inhibitors against the pyruvate dehydrogenase multienzyme complex E1 from Escherichia coli

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8911-8918
DOI: 10.1039/C4OB01347F, PaperLingling Feng, Junbo He, Haifeng He, Lulu Zhao, Lingfu Deng, Li Zhang, Lin Zhang, Yanliang Ren, Jian Wan, Hongwu He
Optimal binding mode for the novel potent inhibitor 4j against PDHc-E1 from E. coli.
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Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-substituted benzo[e]- or [f]isoindolones via Csp2-H functionalization

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8861-8865
DOI: 10.1039/C4OB01644K, PaperPratik A. Ambasana, Dipak D. Vachhani, Marzia Galli, Jeroen Jacobs, Luc Van Meervelt, Anamik K. Shah, Erik V. Van der Eycken
Solvent steers the selectivity: Green and practical Csp2-H functionalization towards N-substituted benzo[e]- or [f]isoindolones.
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Structures, chemotaxonomic significance, cytotoxic and Na+,K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8919-8929
DOI: 10.1039/C4OB01545B, PaperRong-Rong Zhang, Hai-Yan Tian, Ya-Fang Tan, Tse-Yu Chung, Xiao-Hui Sun, Xue Xia, Wen-Cai Ye, David A. Middleton, Natalya Fedosova, Mikael Esmann, Jason T. C. Tzen, Ren-Wang Jiang
New cardenolides with potent cytotoxic and Na+,K+-ATPase inhibitory activities were isolated from the ornamental milkweed Asclepias curassavica.
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Synthesis of oligonucleotides containing N,N-disubstituted 3-deazacytosine nucleobases by post-elongation modification and their triplex-forming ability with double-stranded DNA

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,9011-9015
DOI: 10.1039/C4OB01760A, PaperMasaaki Akabane-Nakata, Satoshi Obika, Yoshiyuki Hari
A post-elongation modification for construction of N,N-disubstituted 3-deazacytosines was developed, and a 2[prime or minute]-O,4[prime or minute]-C-methylene-bridged 3-deazacytidine analog was found for recognition of a CG base pair in triplex DNA.
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The amphiphilic nature of saponins and their effects on artificial and biological membranes and potential consequences for red blood and cancer cells

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8803-8822
DOI: 10.1039/C4OB01652A, Review ArticleJoseph H. Lorent, Joelle Quetin-Leclercq, Marie-Paule Mingeot-Leclercq
Saponins, amphiphiles of natural origin with numerous biological activities, are widely used in research, the cosmetic and pharmaceutical industry.
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Highly diastereoselective 1,3-dipolar cycloadditions of chiral non-racemic nitrones to 1,2-diaza-1,3-dienes: an experimental and computational investigation

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8888-8901
DOI: 10.1039/C4OB01371A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Roberta Majer, Olga Konechnaya, Ignacio Delso, Tomas Tejero, Orazio A. Attanasi, Stefania Santeusanio, Pedro Merino
Asymmetric 1,3-dipolar cycloadditions between 1,2-diaza-1,3-dienes and chiral non-racemic nitrones to give 3-substituted-5-diazenyl isoxazolidines were studied.
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Effect of C7-substitution of 1-arylsulfonyl-5-(N-hydroxyacrylamide)indolines on the selectivity towards a subclass of histone deacetylases

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8966-8976
DOI: 10.1039/C4OB00542B, PaperHsueh-Yun Lee, Li-Ting Wang, Yu-Hsuan Li, Shiow-Lin Pan, Yi-Lin Chen, Che-Ming Teng, Jing-Ping Liou
This study focused on the substitution effect at position C7 of 1-arylsulfonyl-5-(N-hydroxyacrylamide)indolines.
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N- and C-alkylation of seven-membered iminosugars generates potent glucocerebrosidase inhibitors and F508del-CFTR correctors

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8977-8996
DOI: 10.1039/C4OB00325J, PaperJ. Desire, M. Mondon, N. Fontelle, S. Nakagawa, Y. Hirokami, I. Adachi, R. Iwaki, G. W. J. Fleet, D. S. Alonzi, G. Twigg, T. D. Butters, J. Bertrand, V. Cendret, F. Becq, C. Norez, J. Marrot, A. Kato, Y. Bleriot
The synthesis and biological evaluation of a library of novel seven-membered iminosugars is reported.
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Clicked bis-PEG-peptide conjugates for studying calmodulin-Kv7.2 channel binding

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8877-8887
DOI: 10.1039/C4OB01338G, PaperM. Angeles Bonache, Alessandro Alaimo, Covadonga Malo, Oscar Millet, Alvaro Villarroel, Rosario Gonzalez-Muniz
Small bis-conjugates helix A329-350-PEG-triazole-PEG-helix B508-526 (41 residues), prepared through click chemistry of PEGylated peptide derivatives, bind to CaM with nanomolar affinity, behaving as mimics of the Kv7.2 native fragment (239 residues).
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NIS-mediated oxidative cyclization of N-(2-trifluoromethyl-3-alkynyl) hydroxylamines: a facile access to 4-trifluoromethyl-5-acylisoxazoles

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8942-8946
DOI: 10.1039/C4OB01790K, PaperLi Zhang, Qin Zeng, Ao Mao, Ziang Wu, Tian Luo, Yuanjing Xiao, Junliang Zhang
A NIS mediated sequential procedure involving oxidation and electrophilic cycloisomerization of N-(2-trifluoromethyl-3-alkynyl) hydroxylamines for 4-trifluoromethyl-5-acylisoxazole synthesis is developed.
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Stability and bioactivity of thrombin binding aptamers modified with D-/L-isothymidine in the loop regions

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8866-8876
DOI: 10.1039/C4OB01525H, PaperBaobin Cai, Xiantao Yang, Lidan Sun, Xinmeng Fan, Liyu Li, Hongwei Jin, Yun Wu, Zhu Guan, Liangren Zhang, Lihe Zhang, Zhenjun Yang
D-/L-IsoT were used to modify the loop regions of TBA and greatly improved its bioactivity as well as stability.
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Imides modified benzopicenes: synthesis, solid structure and optoelectronic properties

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8902-8910
DOI: 10.1039/C4OB01486C, PaperDi Wu, Haojie Ge, Zhao Chen, Jinhua Liang, Jie Huang, Yufeng Zhang, Xiaoqiang Chen, Xianggao Meng, Sheng Hua Liu, Jun Yin
Imide-modified polycyclic aromatic hydrocarbons can be widely applied in the field of optoelectronic materials.
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A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans from [small alpha]-oxo ketene dithioacetals and propargyl alcohols via domino coupling/annulations

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8947-8951
DOI: 10.1039/C4OB01300J, PaperXiaobing Yang, Fangzhong Hu, Hongjing Di, Xinxin Cheng, Dan Li, Xiaoli Kan, Xiaomao Zou, Qichun Zhang
A convenient base-mediated synthesis of 3-aryol-4-methyl (or benzyl)-2-methylthio furans 2 has been developed through the domino coupling/annulations from [small alpha]-oxo ketene dithioacetals 1 and propargyl alcohols.
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Anion binding of a neutral bis(cyclopeptide) in water-methanol mixtures containing up to 95% water

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8851-8860
DOI: 10.1039/C4OB01497A, PaperFabian Sommer, Stefan Kubik
Selectivity of a synthetic anion receptor reverses from strongly coordinating sulfate to weakly coordinating iodide anions upon increasing the water content of the solution.
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Directed arene/alkyne annulation reactions via aerobic copper catalysis

28 October, 2014 - 10:17

Org. Biomol. Chem., 2014, 12,8844-8850
DOI: 10.1039/C4OB01312C, PaperYi Zhang, Qian Wang, Huidong Yu, Yong Huang
We describe a straightforward protocol for a smooth dehydrogenative annulation reaction between various arenes and terminal alkynes using a catalytic amount of CuBr2 and molecular oxygen.
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