Org. and Biomol. Chem.

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Synthesis of substituted indenones and indanones by a Suzuki-Miyaura coupling/acid-promoted cyclisation sequence

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,728-731
DOI: 10.1039/C3OB41974F, CommunicationAlexey N. Butkevich, Beatrice Ranieri, Lieven Meerpoel, Ian Stansfield, Patrick Angibaud, Andrei Corbu, Janine Cossy
A one-pot Suzuki-Miyaura cross-coupling/acid-catalyzed cyclisation leading to indenones and indanones in modest to good yields is reported.
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Dimerization of a heat shock protein 90 inhibitor enhances inhibitory activity

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,765-773
DOI: 10.1039/C3OB41722K, PaperHendra Wahyudi, Yao Wang, Shelli R. McAlpine
Heat shock protein 90 (hsp90) accounts for 1-2% of the total proteins in normal cells and it functions as a dimer.
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Giant amino acids designed on the polysaccharide scaffold and their protein-like structural interconversion

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,815-822
DOI: 10.1039/C3OB41845F, PaperShun-ichi Tamaru, Daisuke Tokunaga, Kaori Hori, Sayaka Matsuda, Seiji Shinkai
Protein-like polysaccharides possessing pH-responsive structural interconversion were developed. The unique artificial protein model polysaccharides can act as a new potential polymeric host to construct bio-compatible smart materials.
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Fluorescent macrocyclic probes with pendant functional groups as markers of acidic organelles within live cells

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,823-831
DOI: 10.1039/C3OB41773E, PaperPrashant D. Wadhavane, M. Angeles Izquierdo, Dennis Lutters, M. Isabel Burguete, Maria J. Marin, David A. Russell, Francisco Galindo, Santiago V. Luis
A new family of acidity sensitive fluorescent macrocycles has been synthesized and fully characterized.
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Design, synthesis and evaluation of novel tacrine-rhein hybrids as multifunctional agents for the treatment of Alzheimer's disease

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,801-814
DOI: 10.1039/C3OB42010H, PaperSu-Yi Li, Neng Jiang, Sai-Sai Xie, Kelvin D. G. Wang, Xiao-Bing Wang, Ling-Yi Kong
A series of tacrine-rhein hybrid compounds have been designed and synthesized as novel multifunctional potent ChE inhibitors.
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CuI-catalyzed cycloisomerization of propargyl amides

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,795-800
DOI: 10.1039/C3OB42030B, PaperAli Alhalib, Wesley J. Moran
The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported.
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Synthesis and in vitro evaluation of tetrahydroisoquinolines with pendent aromatics as sigma-2 ([sigma]2) selective ligands

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,783-794
DOI: 10.1039/C3OB42254B, PaperMark E. Ashford, Vu H. Nguyen, Ivan Greguric, Tien Q. Pham, Paul A. Keller, Andrew Katsifis
Sigma-2 selective ligands - a SAR study showing increased potency and selectivity with derivatives showing the potential to be converted into radiolabelled ligands.
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Diphenyl-benzo[1,3]dioxole-4-carboxylic acid pentafluorophenyl ester: a convenient catechol precursor in the synthesis of siderophore vectors suitable for antibiotic Trojan horse strategies

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,749-757
DOI: 10.1039/C3OB41990H, PaperEtienne Baco, Francoise Hoegy, Isabelle J. Schalk, Gaetan L. A. Mislin
Diphenyl-benzo[1,3]dioxole-4-carboxylic acid pentafluorophenylester was used in the synthesis of alkyne functionalized bis- and tris-catechol compounds shuttling efficiently iron(III) into E. coli and P. aeruginosa.
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Formation of a pseudo-[small beta]-hairpin motif utilizing the Ant-Pro reverse turn: consequences of stereochemical reordering

22 January, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,774-782
DOI: 10.1039/C3OB42016G, PaperRoshna V. Nair, Amol S. Kotmale, Snehal A. Dhokale, Rupesh L. Gawade, Vedavadi G. Puranik, Pattuparambil R. Rajamohanan, Gangadhar J. Sanjayan
Herein, we report a special case of pseudo-[small beta]-hairpin formation by tetrapeptide sequences featuring a two-residue Ant-Pro dipeptide motif (Ant = anthranilic acid and Pro = proline) at the loop region.
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NMR elucidation of the role of Mg2+ on the structure and stability of the conserved RNA motifs of the EMCV IRES element

20 January, 2014 - 14:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB41840E, PaperVasudevan Ramesh, Sadia Mohammed, Marie M Phelan, Usman Rasul
The three dimensional solution structures of a highly conserved 16mer RNA, endowed with a classic 'GNRA' tetraloop motif, and a 17mer RNA containing a cytosine-rich heptaloop which is predicted to...
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Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization and application to enhancement of electroluminescence

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42070A, PaperChia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo, Yun Chen
Using environmentally stable metal as the cathode in polymer light-emitting diode (PLED) is an essential requirement for its practical application. We present the preparation of water/alcohol soluble copoly(p-phenylene) (P1) containing...
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Fluorene-Based Material Containing Triple Azacrown Ether Groups: Synthesis, Characterization and Application in Chemosensor and Electroluminescent Device

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42054J, PaperChia-Shing Wu, Ying-Ju Lin, Yun Chen
We design a novel multifunctional fluorene-based material containing triple azacrown ether (FTC) to not only apply in aqueous solution of chemosensor towards Fe3+ but also enhance electroluminescence of PLEDs using...
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Deproto-metallation using a mixed lithium-zinc base and computed CH acidity of 1-aryl 1H-benzotriazoles and 1-aryl 1H-indazoles

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42380H, PaperElisabeth NAGARADJA, Floris Chevallier, Thierry Roisnel, Vincent DORCET, Yury Halauko, Oleg A. Ivashkevich, Vadim E. Matulis, Florence Mongin
1-Aryl-1H-benzotriazoles and -1H-indazoles were synthesized, and their deproto-metallation using the base prepared by mixing LiTMP with ZnCl2[round bullet, filled]TMEDA (1/3 equiv) was studied. In the indazole series, reactions occuring at the 3...
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A cascading reaction sequence involving ligand-directed azaelectrocyclization and autooxidation-induced fluorescence recovery enables visualization of target proteins on the surfaces of live cells

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42267D, PaperKatsunori Tanaka, Masataka Kitadani, Ayumi Tsutsui, Ambara R. Pradipta, Rie Imamaki, Shinobu Kitazume, Naoyuki Taniguchi, Koichi Fukase
A general probe designed to induce a cascading sequence of reactions on a target protein was efficiently synthesized. The cascading reaction sequence involved (i) ligand-directed azaelectrocyclization with lysine, and (ii)...
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Out-Basicity of 1,8-bis(dimethylamino)naphthalene: The experimental and theoretical challenge

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB41986J, PaperValery A. Ozeryanskii, Alexander F. Pozharskii, Alexander S. Antonov, Aleksander Filarowski
A possibility of nonconventional two-step protonation of 1,8-bis(dimethylamino)naphthalene (proton sponge) is discussed. Unlike generally accepted mechanism, involving relatively slow direct penetration of a proton into the cleft between the peri-NMe2...
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Oxenoids in Organic Synthesis

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42349B, Review Articlellan Marek, Yury Minko
Recent studies focused on the reactivity of metalated peroxides as oxenoids (electrophilic oxidants) revealed their unique properties allowing for highly selective and efficient oxidation processes involving nucleophilic organometallics. In this...
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Synthesis of Polysubstituted Pyrroles via [3 + 2]-Annulation of Aziridines and [small beta]-Nitroalkenes Under Aerobic Conditions

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42324G, PaperShaoYin Wang, Zhu Xiancui, Zhuo Chai, Shaowu Wang
Polysubstituted pyrroles were regioselectively synthesized in moderate to good yields via the copper acetate-catalyzed [3 + 2] annulation reaction of readily accessible aziridines and nitroalkenes. This reaction was proposed to...
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Cationic lipophosphoramidates with two different lipid chains: synthesis and evaluation as gene carriers.

16 January, 2014 - 13:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42270D, PaperPaul-Alain Jaffres, Stephanie Sandra Le Corre, Mathieu Berchel, Nawal Belmadi, Caroline Denis, Jean-Pierre Haelters, Pierre Lehn, Tristan Montier, Tony Le GAll
Cationic lipids constitute a family of synthetic vectors commonly used for nucleic acids delivery. We herein report the results of a systematic study that aimed to compare the transfection efficacies...
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Huisgen-based conjugation of water-soluble porphyrins to deprotected sugars: towards mild strategies for the labelling of glycans

14 January, 2014 - 12:54
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42306A, CommunicationRoss W Boyle, Francesca Giuntini, Francesca Bryden, Eoin Scanlan, Robin Daly
Fully deprotected alkynyl-functionalised mono- and oligosaccharides undergo CuAAC-based conjugation with water-soluble porphyrin azides in aqueous environments. The mild reaction conditions are fully compatible with the presence of labile glycosidic bonds....
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A remarkable regiocontrol in the palladium-catalyzed silylstannylation of fluoroalkylated alkynes -Highly regio- and stereoselective synthesis of multi-substituted fluorine-containing alkenes

14 January, 2014 - 12:54
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB41903G, PaperTsutomu Konno, Ryoko Kinugawa, Takashi Ishihara, Shigeyuki Yamada
On treating fluorine-containing internal alkynes with 1.2 equiv of (trimethylsilyl)tributyltin in the presence of 2.5 mol% of Pd(PPh3)2Cl2 in THF at the reflux temperature for 6 h, the silylstannylation reaction...
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