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Design, synthesis and biological evaluation of bicyclic iminosugar hybrids: conformational constraint as an effective tool for tailoring the selectivity of [small alpha]-glucosidase inhibitors

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00486H, PaperInderpreet Arora, Vivek Kr. Kashyap, Alok Kumar Singh, Arunava Dasgupta, Brijesh Kumar, Arun K. Shaw
Selective inhibition by conformational restriction of pyrrolidine iminosugars. Click conceived pyrrolidotriazoles incorporate essential features to access the mimicry of the transition state of carbohydrate processing enzymes.
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Copper-catalyzed arylsulfonylation of N-arylsulfonyl-acrylamides with arylsulfonohydrazides: synthesis of sulfonated oxindoles

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01231C, CommunicationQingshan Tian, Ping He, Chunxiang Kuang
A copper-catalyzed arylsulfonylation of N-arylsulfonyl-acrylamides with sulfonylhydrazides through a tandem radical process was developed.
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Asymmetric borylation of [small alpha],[small beta]-unsaturated esters catalyzed by novel ring expanded N-heterocyclic carbenes based on chiral 3,4-dihydro-quinazolinium compounds

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01101E, CommunicationLiliang Huang, Yong Cao, Manping Zhao, Zhongfeng Tang, Zhihua Sun
A series of novel ring expanded N-heterocyclic carbene (NHC) precursors were synthesized, which showed excellent enantioselectivities for borylation of [small alpha],[small beta]-unsaturated esters.
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Comparison of the substrate selectivity and biochemical properties of human and bacterial [gamma]-butyrobetaine hydroxylase

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01167H, CommunicationAnna M. Rydzik, Ivanhoe K. H. Leung, Grazyna T. Kochan, Nikita D. Loik, Luc Henry, Michael A. McDonough, Timothy D. W. Claridge, Christopher J. Schofield
BBOX is a 2-oxoglutarate dependent oxygenase that can catalyse formation of vicinal diols and amino alcohols.
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Total synthesis of the cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids derived from 2-hydroxy-6-methylcarbazole

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01151A, PaperCemena Gassner, Ronny Hesse, Arndt W. Schmidt, Hans-Joachim Knolker
The synthesis of seven pyrano[3,2-a]carbazole alkaloids has been achieved using their putative biogenetic precursor 2-hydroxy-6-methylcarbazole as key intermediate.
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Demonstration of a common indole-based aromatic core in natural and synthetic eumelanins by solid-state NMR

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01066C, PaperSubhasish Chatterjee, Rafael Prados-Rosales, Sindy Tan, Boris Itin, Arturo Casadevall, Ruth E. Stark
Comparing natural and synthetic eumelanin pigment structures: high-field 2D solid-state NMR reveals a common indole-based aromatic core for ubiquitous protective pigments that inspire engineered materials.
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Fluorous chiral bisoxazolines: application in copper-catalyzed asymmetric [small alpha]-hydrophosphonylation

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5843-5846
DOI: 10.1039/C4OB01144A, CommunicationTao Deng, Hongjun Wang, Chun Cai
A copper-catalyzed asymmetric [small alpha]-hydrophosphonylation of isatins with a novel fluorous bis(oxazoline) as a ligand is presented.
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A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines via dual C(sp3)-H/C(sp2)-H functionalizations

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5839-5842
DOI: 10.1039/C4OB01256A, CommunicationZhi-Qiang Zhu, Tian-Tian Wang, Peng Bai, Zhi-Zhen Huang
A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines has been developed through dual C(sp3)-H/C(sp2)-H functionalizations.
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N-Bromoacetamide-mediated domino cyclization and elimination of homoallylic trichloroacetimidates: a novel approach toward the synthesis of 1-bromo-2-amino-3-butene derivatives

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01126K, PaperRui Zhu, Kai Yu, Zhenhua Gu
Allylic amides 3 were synthesized efficiently from homoallylic trichloroacetimidates 1 via domino bromo-cyclization and elimination reactions.
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Novel phthalamides containing sulfiliminyl moieties and derivatives as potential ryanodine receptor modulators

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00716F, PaperSha Zhou, Tao Yan, Yuxin Li, Zhehui Jia, Baolei Wang, Yu Zhao, Yuanyuan Qiao, Lixia Xiong, Yongqiang Li, Zhengming Li
The present work firstly reported that the new diamides incorporating sulfiliminyl moieties are potential candidate structures for new ryanodine receptor modulators.
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Stereoselective one-pot synthesis of [small beta]-alkylsulfide enol esters. Base-triggered rearrangement under mild conditions

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01011F, PaperAdrian A. Heredia, Silvia M. Soria-Castro, Lydia M. Bouchet, Gabriela Oksdath-Mansilla, Cecilia A. Barrionuevo, Daniel A. Caminos, Fabricio R. Bisogno, Juan E. Arguello, Alicia B. Penenory
(Z)-Vinyl sulfides are easily synthesised through a multicomponent reaction. An intramolecular S,O-acyl migration accounts for the observed stereoselectivity.
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Syntheses and characterization of liposome-incorporated adamantyl aminoguanidines

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,6005-6013
DOI: 10.1039/C4OB00592A, PaperMarina Sekutor, Adela Stimac, Kata Mlinaric-Majerski, Ruza Frkanec
A series of mono and bis-aminoguanidinium adamantane derivatives has been synthesized and incorporated into liposomes.
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Studies on copper(I)-catalyzed highly regio- and stereo-selective hydroboration of alkynamides

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5945-5953
DOI: 10.1039/C4OB00979G, PaperGuangke He, Shan Chen, Qiang Wang, Hai Huang, Qijun Zhang, Dongming Zhang, Rong Zhang, Hongjun Zhu
The regio-selectivity of the Cu(I)-catalyzed hydroboration of N-(1-alkynyl)amides is unexpectedly opposite to that in the carbometallation reaction of alkynamides.
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Structurally modified natural sesquiterpene lactones constitute effective and less toxic schistosomicidal compounds

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00426D, PaperDaiane Cristina Sass, Gustavo Oliveira Morais, Ricardo Augusto Crema Miranda, Lizandra Guidi Magalhaes, Wilson Roberto Cunha, Raquel Alves dos Santos, Nilton Syogo Arakawa, Fernando Batista Da Costa, Mauricio Gomes Constantino, Vladimir Constantino Gomes Heleno
Selective obtention of novel natural sesquiterpene lactone derivatives with interesting schistosomicidal activity and low toxicity, together with complete NMR assignments.
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Synthesis of 3,3-disubstituted-2,3-dihydroazanaphthoquinones via simultaneous alkyne oxidation and nitrile hydration of ortho-alkynylarenenitriles

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00852A, PaperKaruppusamy Sakthivel, Kannupal Srinivasan
Simultaneous activation of alkynes and nitriles in o-alkynylarenenitriles in the presence of Pd(OAc)2/H2O/(+/-)-CSA afforded 3,3-disubstituted-2,3-dihydroazanaphthoquinones in moderate to excellent yields.
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Solid-phase synthesis of peptoid-like oligomers containing diverse diketopiperazine units

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, 12,5831-5834
DOI: 10.1039/C4OB00829D, CommunicationSujit Suwal, Thomas Kodadek
An efficient protocol for the solid-phase synthesis of diverse diketopiperazines is reported.
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An acridinium-based sensor as a fluorescent photoinduced electron transfer probe for proton detection modulated by anionic micelles

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00559G, PaperStefano Basili, Tiziana Del Giacco, Fausto Elisei, Raimondo Germani
Photoinduced electron transfer has been demonstrated to be the quenching mechanism for the fluorescent pH sensor based on the 9-amino-10-methylacridinium chromophore. The presence of anionic micelles causes a significant increase in the detection sensitivity of pH.
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SN2 regioselectivity in the esterification of 5- and 7-membered azacycloalkane quaternary salts: a DFT study to reveal the transition state ring conformation prevailing over the ground state ring strain

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00695J, PaperAkihiro Kimura, Susumu Kawauchi, Takuya Yamamoto, Yasuyuki Tezuka
SN2 regioselectivity in 5- and 7-membered azacycloalkanes quaternary salts is directed by the transition state ring conformation.
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Synthesis and evaluation of antineurotoxicity properties of an amyloid-[small beta] peptide targeting ligand containing a triamino acid

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00959B, PaperDmytro Honcharenko, Partha Pratim Bose, Jyotirmoy Maity, Firoz Roshan Kurudenkandy, Alok Juneja, Erik Floistrup, Henrik Biverstal, Jan Johansson, Lennart Nilsson, Andre Fisahn, Roger Stromberg
A new triamino acid enables synthesis of an amyloid-[small beta] peptide (A[small beta]) targeting ligand with additional A[small beta]-ligand interactions that gives protection towards A[small beta]-induced reduction of gamma oscillations in hippocampal slice preparation.
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Convenient access to readily soluble symmetrical dialkyl-substituted [small alpha]-oligofurans

Org. and Biomol. Chem. - 23 July, 2014 - 09:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00898G, PaperEdward E. Korshin, Gregory M. Leitus, Michael Bendikov
A combination of heteroatom directed lithiation/CuCl2-induced homocoupling, Wittig olefination/Pd-catalyzed transfer hydrogenation followed by Suzuki-Miyaura or Stille cross-coupling enables convenient access to dialkyl-substituted [small alpha]-oligofurans of potential interest for organic electronics.
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