Royal Society of Chemistry

Regioselective Ruthenium catalysed H-D exchange using D2O as the deuterium source

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01798F, PaperSteve Nolan, Simone Manzini, Jose Fernandez-Salas, Lorenzo Piola
An efficient and convenient ruthenium catalysed method for a regiospecific H/D exchange using D2O is described. Organic moieties such as pyridine, oxazole, imidazole, pyrazole, ester, ketone and carboxylic acid have...
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Catalyst-Free Reductive Amination of Aromatic Aldehydes with Ammonium Formate and Hantzsch Ester

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01590H, CommunicationPan-Pan Zhao, Xin-Feng Zhou, Jian-Jun Dai, Hua-Jian Xu
The protocol of the reductive amination of aromatic aldehydes using ammonium formate and Hantzsch Ester is described. It's a mild, convenient, acid- and catalyst-free system applied for the synthesis of...
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Chemical and biological evaluation of unusual sugars, [small alpha]-aculosides, as novel Michael acceptors

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01877J, CommunicationHiromasa Ikeda, Erika Kaneko, Shunsuke Okuzawa, Daisuke Takahashi, Kazunobu Toshima
The unusual sugars [small alpha]-aculosides, which appear in certain antibiotics and have an [small alpha],[small beta]-unsaturated ketone structure, were found to be novel and selective Michael acceptors for the thiol function of cysteine...
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A straightforward modification in the thrombin binding aptamer improving stability, affinity to thrombin and nuclease resistance

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01475H, CommunicationAldo Galeone, Veronica Esposito, maria scuotto, Antonella Capuozzo, Rita Santamaria, Michela Varra, Luciano Mayol, Antonella Virgilio
Degradation of nucleic acids in biological environments is a major drawback of the therapeutic use of aptamers. Among approaches used to circumvent this negative aspect, the introduction of 3'-3' inversion...
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TBHP-promoted sequential carboxamidation and aromatisation of aryl isonitriles with formamides

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01850H, PaperJin-Tao Yu, Xiaomei Feng, Hui Zhu, Lei Wang, Yan Jiang, Jiang Cheng
The tert-butyl hydroperoxide (TBHP)-promoted sequential carboxamidation and aromatisation of isonitriles with formamides was developed. This procedure tolerates a series of functional groups, such as methyl, fluoro, chloro, acetyl, methoxy carbonyl...
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Organocatalytic enantioselective [small alpha]-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01921K, CommunicationBaomin Wang, Huanrui Zhang, Longchen Cui, Ying Li, Jingping Qu, Yuming Song
We report a highly efficient approach to construct chiral N,S-acetals using 5-substituted rhodanines as sulfur-bound pronucleophiles catalyzed by natural cinchona alkaloids quinine or quinidine. This [small alpha]-amination reaction has a broad...
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The design, synthesis and biological evaluation of novel thiamin diphosphate analog inhibitors against pyruvate dehydrogenase multienzyme complex E1 from Escherichia coli

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01347F, Paperlingling feng, Junbo He, Haifeng He, Lulu Zhao, Lingfu Deng, Li Zhang, Lin Zhang, yanliang ren, Jian Wan, Hongwu He
Pyruvate dehydrogenase multienzyme complex E1 (PDHc E1) is a potential target enzyme for finding inhibitors to combat microbial disease. In this study, we designed and synthesized a series of novel...
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Solvent switchable cycloaddition: a (one-pot) metal-free approach towards N-subsituted benzo[e]- or [f]isoindolones via Csp2-H functionalization

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01644K, PaperPratik A Ambasana, Dipak D Vachhani, Marzia Galli, Jeroen Jacobs, Luc Van Meervelt, Anamik shah, Erik V�lery Van der Eycken
The tuning of selective ring closure is a nontrivial challenge in synthetic organic chemistry. Herein we report a solvent switchable metal-free [4+2] cycloaddition approach via Csp2-H functionalization. The protocol is...
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Organocatalysts of oxidative protein folding inspired by protein disulphide isomerase

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01738B, CommunicationJohn C. Lukesh, Kristen A. Andersen, Kelly K. Wallin, Ronald T. Raines
Organocatalysts derived from diethylenetriamine effect the rapid isomerization of non-native protein disulfide bonds to native ones. These catalysts contain a pendant hydrophobic moiety to encourage interaction with the non-native state,...
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Relative stability of benziporphyrin and naphthiporphyrin tautomers and the emergence of macrocyclic diatropicity

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01659A, PaperTimothy D Lash, Deyaa I AbuSalim
The conformations of a series of benziporphyrins, naphthiporphyrins, oxybenziporphyrins, and related structures were minimized using DFT-B3LYP/6-311++G(d,p). The relative stabilities of the tautomers for each series were also calculated using M06-2X...
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Structures, chemotaxonomic significance, cytotoxic and Na+,K+-ATPase inhibitory activities of new cardenolides from Asclepias curassavica

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
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 Middleton, Natalya Fedosova, Mikael Esmann, Jason T.C. Tzen, Renwang Jiang
Five new cardenolide lactates (1-5) and one new dioxane double linked cardenolide glycoside (17) along with 15 known compounds (6-16 and 18-21) were isolated from the ornamental milkweed Asclepias curassavica....
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2-Alkynylbenzaldoxime: A versatile building block for the generation of N-heterocycles

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01618A, Review ArticleLinman He, Guanyinsheng Qiu, Yueqiu Gao, Jie Wu
2-Alkynylbenzaldoxime as a versatile building block has been applied widely for the construction of N-heterocycles in organic synthesis. Since it could be easily transferred to isoquinoline N-oxide via intramolecular 6-endo...
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Selective chromo-fluorogenic detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) with a unique probe based on a boron dipyrromethene (BODIPY) dye

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01299B, PaperAna M. Costero, Andrea Barba Bon, Salvador Gil, Ramon Martinez-Manez, Felix Sancenon
A novel colorimetric probe (P4) for the selective differential detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) was prepared. Probe P4 contains three reactive sites;...
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Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01743A, PaperMAYA SHANKAR SINGH, Tanmoy Chanda, Sushobhan Chowdhury, Suvajit Koley, Namrata Anand
A facile and efficient synthesis of chromen-4-one and isoflavone frameworks has been achieved by domino C-acylation/O-acylation/aldolization sequence. This operationally simple one-pot elegant strategy provides structurally unique chromen-4-ones and isoflavones directly...
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Influence of the aromatic aglycon of galactoclusters on the binding of LecA: Case study with O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl aglycons

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01599A, PaperFrancesca Casoni, Lucie Dupin, Gerard Vergoten, Albert Meyer, Caroline Ligeour, Thomas Gehin, Olivier Vidal, Eliane Souteyrand, Jean-Jacques Vasseur, Yann Chevolot, Francois Morvan
A library of 24 new mannose-centered tetragalactoclusters with four different linkers (di- and triethyleneglycol with phosphodiester or phosphorothioate linkages) and six different aromatic aglycons (O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and...
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Rhodium(II) catalyzed synthesis of macrocycles incorporating oxindole via O-H/N-H insertion reactions

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01671H, PaperSengodagounder Muthusamy, Thangaraju Karikalan
A wide variety of 10- to 29-membered oxaza-macrocycles incorporating oxindole unit were synthesized in good yield via rhodium(II) acetate dimer catalyzed intramolecular O-H/N-H insertion reactions. Interestingly, synthesis of C2-symmetric macrocycles...
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Discovery and synthesis of a novel series of potent, selective inhibitors of the PI3K[small alpha]: 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01589D, PaperYong Yin, Xun Wu, Hong-Wei Han, Shao Sha, She-Feng Wang, Fang Qiao, Aimin Lu, Peng-Cheng Lv, Hai-Liang Zhu
A series of novel 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives were synthesized and evaluated their biological activities as PI3K inhibitors. In vitro biological evaluation against four human tumor cell lines revealed that most target...
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Synthesis, Gelation and Topochemical Polymerization of meta-Linked Oligophenylenebutadiynylene Derivatives

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01322K, PaperIsabelle Levesque, Simon Rondeau-Gagne, Jules Romeo Neabo, Jean-Francois Morin
Rational design of meta-linked oligophenylbutadiynylene (OPBDs) derivatives has been conducted in order to gain insights on their gelation properties and reactivity toward topochemical polymerization to yield polydiacetylenes (PDAs). Different structural...
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Theoretical study of ternary indole-cation-anion complexes

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01879F, PaperJorge A. Carrazana-Garcia, Enrique M. Cabaleiro-Lago, Alba Campo-Cacharron, Jesus Rodriguez-Otero
The simultaneous interactions of an anion and a cation with a [small pi] system have been investigated using MP2 and M06-2X theoretical calculations. Indole was chosen as a model [small pi] system...
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Robust Asymmetric Synthesis of Unnatural Alkenyl Amino Acids for Conformationally Constrained [small alpha]-Helix Peptides

Org. and Biomol. Chem. - 22 September, 2014 - 02:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01832J, PaperAndrew George Jamieson, Boris Aillard, Naomi Stephanie Robertson, Adam Baldwin, Siobhan Robins
A series of enantiopure unnatural alkenyl amino acids required for peptide 'stapling' have been synthesised in good overall yields using NiII Schiff base complexes derived from a (S)-N-(2-benzoylphenyl)-1-(2-fluorobenzyl)-pyrrolidine-2-carboxamide 4 (2-FBPB)...
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