Org. and Biomol. Chem.

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Synthesis and spectroscopic properties of novel meso-cyano boron-pyridyl-isoindoline dyes

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01077A, PaperHui Liu, Hua Lu, Fan Wu, Zhifang Li, Nagao Kobayashi, Zhen Shen
Meso-cyano boron-pyridyl-isoindoline dyes with asymmetrical structures have been synthesized through a facile two-step reaction. Broad envelopes of intense vibrational bands are observed for the main spectral bands in the absorption...
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Stereoselective Intermolecular [2 + 2]-Photocycloaddition Reactions of Maleic Anhydride: Stereocontrolled and Regiocontrolled Access to 1,2,3-Trifunctionalized Cyclobutanes

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01383B, PaperFlorian HERNVANN, Gloria RASORE, Valerie DECLERCK, David J Aitken
Short synthetic sequences commencing with the photosensitized [2 + 2] cycloaddition reactions of maleic anhydride with either allyl alcohol or propargyl alcohol have been elaborated to provide access to 1,2,3-trisubstituted...
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Coumarin-Pterocarpan Conjugate- A Natural Product Inspired Hybrid Molecular Probe for DNA Recognition

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01360C, PaperShital K Chattopadhyay, Indranil Kundu, Ratnava Maitra
Thermally induced cascade sigmatropic rearrangement of a butynyloxycoumarin derivative has led to a quick access of coumarin-pterocarpan hybrid molecule. Biophysical studies together with molecular modeling show that this nature-inspired hybrid...
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Surface Patterning with Natural and Synthetic Polymers via an inverse Electron Demand Diels-Alder Reaction employing Microcontact Chemistry

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01379D, PaperOliver Roling, Artur Mardykov, Sebastian Lamping, Benjamin Vonhoeren, Stefan Rinnen, Heinrich Arlinghaus, Armido STUDER, Bart Jan Ravoo
Bioorthogonal ligation methods are the focus of current research due to their versatile applications in biotechnology and materials science for post-functionalization and immobilization of biomolecules. Recently, inverse electron demand Diels-Alder...
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The effects of CO2 pressure and pH on the Suzuki coupling of basic nitrogen containing substrates

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01630K, PaperC. Senter, A. Rumple, W. Medina-Ramos, D. Houle, Z. Cheng, C. Gelbaum, J. Fisk, B. Holden, P. Pollet, C. A. Eckert, Charles L. Liotta
The Suzuki coupling reaction of basic nitrogen containing substrates (2-bromo- and 2-chloro-4-aminopyridine, and 2-bromo and 2-chloropyridine) with phenylboronic acid using Pd(TPP)2Cl2/K3PO4 in acetonitrile-water biphasic solvent systems under a CO2 or a N2 atmosphere is discussed.
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Fast redox-triggered shuttling motions in a copper rotaxane based on a phenanthroline-terpyridine conjugate

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01206B, PaperEugenio Coronado, Pablo Gavina, Julia Ponce, Sergio Tatay
Fast shuttling motions in solution have been observed for a Cu-complexed [2] rotaxane, whose thread contains a bidentate 1,10-phenanthroline chelating unit directly connected through its 3-position to the 5-position of a tridentate 2,2[prime or minute]:6[prime or minute],2[prime or minute][prime or minute]-terpyridine.
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Evolution of a strategy for preparing bioactive small molecules by sequential multicomponent assembly processes, cyclizations, and diversification

20 August, 2014 - 18:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00835A, Review ArticleJames J. Sahn, Brett A. Granger, Stephen F. Martin
Multicomponent assembly processes are key steps in the synthesis of diverse polycyclic heterocycles with a broad array of biological activities.
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Exploring functional cyclophellitol analogues as human retaining beta-glucosidase inhibitors

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01611D, PaperHerman S. Overkleeft, Kah-Yee Li, Jianbin Jiang, Martin Witte, Wouter W Kallemeijn, Wilma Donker-Koopman, Rolf Boot, Johannes M. F. G. Aerts, Jeroen D Codee, Gijsbert A van der Marel
The natural product, cyclophellitol and its aziridine analogue are potent mechanism-based retaining [small beta]-glucosidase inhibitors. In this paper we explore the inhibitory potency of a number of cyclophellitol analogues against the...
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Theoretical insight into the antioxidant properties of melatonin and derivatives

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01396D, PaperJeffrey R Johns, James A Platts
Density functional theory calculations on melatonin, metabolites and synthetic derivatives thereof, and a range of other biological antioxidant molecules are presented, with a view to understanding the antioxidant ability of...
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First Synthesis of the Antiangiogenic Homoisoflavanone, Cremastranone

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01604A, CommunicationBit Lee, Halesha D Basavarajappa, Rania Sulaiman, Xiang Fei, Seung-Yong Seo, Timothy William Corson
An antiangiogenic homoisoflavanone, cremastranone, was synthesized for the first time. This scalable synthesis, which includes selective demethylation, could be used to develop lead molecules to treat angiogenesis-induced eye diseases. Synthetic...
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9-amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01648C, PaperWenwen Peng, Jingwei Wan, xuebing ma, Bing Xie
A new class of 9-amino-(9-deoxy) cinchona alkaloid-derived chiral phase-transfer catalysts bearing amino groups was developed by using the known cinchona alkaloids as starting materials. Due to the transformation of 9-hydroxyl...
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Correction: Identification and optimization of short helical peptides with novel reactive functionality as catalysts for acyl transfer by reactive tagging

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB90119C, CorrectionSilvia Bezer, Masaomi Matsumoto, Michael W. Lodewyk, Stephen J. Lee, Dean J. Tantillo, Michel R. Gagne, Marcey L. Waters
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A Lewis acid-mediated conformational switch

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01556H, PaperPeter Clarke Knipe, Hannah Lingard, Ian M Jones, Sam Thompson, Andrew D Hamilton
Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis...
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Neither azeotropic drying, nor base, nor other additives - a minimalist approach to 18F-labeling

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014
DOI: 10.1039/C4OB01336K, PaperRaphael Richarz, Philipp Krapf, Elizaveta Alexandrovna Urusova, Bernd Neumaier, Boris Dmitrievitch Zlatopolskiy
A novel, efficient, time-saving and reliable radiolabeling procedure via nucleophilic substitution with [18F]fluoride is described. Different radiolabeled aliphatic and aromatic compounds were prepared in high radiochemical yields simply by the...
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Origins of exo-Stereoselectivity of Norbornene in Hetero Diels-Alder Reactions

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01217H, PaperSesil Agopcan, Selami Ercan, Sule Erol, Ilknur Dogan, Viktorya Aviyente
In this study the exo selectivity in the hetero Diels-Alder reaction of atropisomeric 5-benzylidine-2-arylimino-3-aryl-thiazolidine-4-thiones with norbornene has been investigated with computational tools. Taking into account the M/P chiral character of...
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Non-isoprenoid Polyene Natural Products - Structures and Synthetic Strategies

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01337A, Review ArticleAndrew Whiting, Katrina Madden, Fathia Mosa
This review provides insight into the variety of structures and biological activities found in the non-isoprenoid family of polyene natural products and examines the strategies and synthetic methods applied for...
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Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01358A, PaperXuan Zhao, Tian-Ze Li, Jing-Ying Qian, Feng Sha, Xin-Yan Wu
The first enantioselective aza-Morita-Baylis-Hillman reaction of acrylates with ketimines derived from isatins has been developed. With 2 mol% of chiral bifunctional phosphine-squaramide 4e, optically active 3-substituted-3-amino-2-oxindoles were obtained in excellent...
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Iron-catalyzed direct difunctionalization of alkenes with dioxygen and sulfinic acids: a highly efficient and green approach to [small beta]-ketosulfones

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01369G, CommunicationHua Wang, Wei Wei, Jiangwei Wen, Daoshan Yang, Min Wu, Jinmao You
A novel iron-catalyzed direct difunctionalization of alkenes with sulfinic acids and dioxygen for the synthesis of [small beta]-ketosulfones has been developed under mild conditions. The present protocol, which utilizes inexpensive iron...
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Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01063A, Review ArticleAlexander Drohat, Atanu Maiti
DNA glycosylases remove damaged or enzymatically modified nucleobases from DNA, thereby initiating the base excision repair (BER) pathway, which is found in all forms of life. These ubiquitous enzymes promote...
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A Small Synthetic Molecule Forms Selective Potassium Channels to Regulate Cell Membrane Potential and Blood Vessel Tone

20 August, 2014 - 18:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01420K, PaperD Yang, Hui-Yan Zha, Bing Shen, Kwok-Hei Yau, Shing-To Li, Xiao-Qiang Yao
In living cell membranes, K+ permeability is higher than other ions such as Na+ and Cl- owing to abundantly expressed K+ channels. Polarized membrane potential is mainly established by K+...
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