Org. and Biomol. Chem.

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Benzimidazoles and benzoxazoles via the nucleophilic addition of anilines to nitroalkanes

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00131E, PaperAlexander V Aksenov, Alexander N Smirnov, Nicolai A Aksenov, Asiyat S Bijieva, Inna V Aksenova, Michael Rubin
PPA-induced umpolung triggers efficient nucleophilic addition of unactivated anilines to nitroalkanes to produce N-hydroxyimidamides. The latter undergo sequential acid-promoted cyclocondensation with ortho-OH or ortho-NHR moieties to afford benzoxazoles and benzimidazoles,...
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Synthesis of 2-Anilinopyridyl-Triazole Conjugates as Antimitotic Agents

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00232J, PaperAhmed Kamal, Subba Rao A.V., Vishnuvardhan MVPS, Srinivas Reddy T, Swapna Konderu, chandrakant Bagul, Subba Reddy N. V., vunnam srinivasulu
A series of 2-anilinopyridyl-triazole conjugates (6a-t) were prepared and evaluated for their cytotoxic activity against a panel of three human cancer cell lines. Among them compounds 6q, 6r and 6s...
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IDB-containing low molecular weight short peptide as efficient DNA cleavage reagent

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02518K, PaperChunying Ma, Huan Chen, Chao Li, Jin Zhang, Renzhong Qiao
Artificial nucleases have attracted significant interest due to their abilities in accelerating DNA cleavage, which makes the possibility of genome manipulation. However, compared with natural nucleases, currently available artificial nucleases...
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"Off-On" Aggregation-Based Fluorescent Sensor for the Detection of Chloride in Water

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02409E, PaperMichelle M. Watt, Jeffrey M Engle, Kurtis C. Fairley, Timothy E Robitshek, Michael M Haley, Darren Johnson
Receptors selective for anions in aqueous media are a crucial component in the detection of anions for biological and environmental applications. Recent sensor designs have taken advantage of systems known...
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Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00157A, PaperS. De, E. Groaz, L. Margamuljana, M. Abramov, P. Marliere, P. Herdewijn
The incorporation and extension of synthetically unprecedented nucleoside phosphoramidate sulfonates is demonstrated using thermophilic and mesophilic microbial polymerases.
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Sodium Periodate Mediated Oxidative Transformations in Organic Synthesis

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00238A, Review ArticleSudalai Arumugam, Alexander M. Khenkin, Ronny Neumann
Investigation of new oxidative transformation for the synthesis of carbon-heteroatom and heteroatom-heteroatom bonds is of fundamental importance in the synthesis of numerous bioactive molecules and fine chemicals. In this context,...
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Flow Synthesis of Ethyl Isocyanoacetate Enabling the Telescoped Synthesis of 1,2,4-Triazoles and Pyrrolo-[1,2-c]pyrimidines

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00245A, PaperMarcus Baumann, Antonio M. Rodriguez Garcia, Ian R Baxendale
The efficient flow synthesis of important heterocyclic building blocks based on the 1,2,4-triazole and pyrrolo[1,2-c]pyrimidine scaffold has been achieved. Crucially, a telescoped continuous flow process was developed based on the...
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Visible Light Mediated sp3 C-H Bond Functionalization of N-Aryl-1,2,3,4-tetrahydroisoquinolines via Ugi-type Three-component Reaction

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00201J, PaperYunyun Chen, Gaofeng Feng
An efficient and high yield process for sp3 C-H bond functionalization of N-aryl-1,2,3,4-tetrahydroisoquinolines was disclosed through a visible light mediated photoredox Ugi-type reaction with carboxylic acids and isonitriles under aerobic...
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N-Branched acyclic nucleoside phosphonates as monomers for the synthesis of modified oligonucleotides

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02265C, PaperDana Hockova, Sarka Rosenbergova, Petra Menova, Ondrej Pav, Radek Pohl, Pavel Novak, Ivan Rosenberg
Protected N-branched nucleoside phosphonates containing adenine and thymine bases were prepared as the monomers for the introduction of aza-acyclic nucleotide units into modified oligonucleotides. The phosphotriester and phosphoramidite methods were...
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Editorial: Recognition and reactivity at interfaces

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB90040A, EditorialPaolo Scrimin
Showcasing a collection of cutting edge contributions on the topic of Recognition and Reactivity at Interfaces.
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3-(Benzo[d][1,3]dioxol-5-ylamino)-N-(4-fluorophenyl)thiophene-2-carboxamide overcomes cancer chemoresistance via inhibition of angiogenesis and P-glycoprotein efflux pump activity

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00233H, PaperRamesh Mudududdla, Santosh Guru, Abubakar Wani, Sadhana Sharma, Prashant Joshi, Ram A Vishwakarma, Ajay Kumar, Shashi Bhushan, Sandip Bibishan Bharate
3-((Quinolin-4-yl)methylamino)-N-(4-(trifluoromethoxy)phenyl)thiophene-2-carboxamide (OSI-930, 1) is a potent inhibitor of c-kit and VEGFR2, currently under phase I clinical trials in patients with advanced solid tumors. In order to understand the structure-activity relationship,...
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Conformationally restricted 3[prime or minute]-modified ABA analogs for controlling ABA receptors

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02662D, PaperJun Takeuchi, Toshiyuki Ohnishi, Masanori Okamoto, Yasushi Todoroki
The physiological functions of abscisic acid (ABA) are regulated by a signal transduction pathway involving cytosolic ABA receptors, which include 14 PYR/PYL/RCAR (PYL) proteins in Arabidopsis. The development of a...
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Oxidative Cleavage of Allyl Ethers by an Oxoammonium Salt

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00270B, PaperChristopher Kelly, John Ovian, Robin Cywar, Taylor Gosselin, Rebecca Wiles, Nicholas E. Leadbeater
A method to oxidatively cleave allyl ethers to their corresponding aldehydes mediated by an oxoammonium salt 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (4-NHAc-TEMPO+ BF-4, 1a) is described. Using a biphasic solvent system and mild...
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PYRROC: the first functionalized cycloalkyne that facilitates isomer-free generation of organic molecules by SPAAC

2 March, 2015 - 16:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C5OB00212E, CommunicationCorinna Grost, Thorsten Berg
PYRROC is the first functionalized cycloalkyne which cannot form isomers in the strain-promoted cycloaddition with azides, and displays unprecedented rate accelerations and rate constants in aqueous buffer.
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Synthesis and structural reconfirmation of bacillamide B

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00093A, PaperXue Sun, Yi Liu, Jun Liu, Guofenggu GU, Yuguo Du
A concise total synthesis of natural product bacillamide B was accomplished in 30% overall yield starting from L-Cystine. The key step was a one-pot four-step process of thiazoline formation via...
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One-pot Total Synthesis of Streptindole, Arsindoline B and Their Congeners Through Tandem Decarboxylative Deaminative Dual-Coupling Reaction of Amino Acids with Indoles

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00025D, PaperJia-Chen Xiang, Jun-Gang Wang, Miao Wang, Xiang-Gao Meng, An-Xin Wu
This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and further applied to one-pot total synthesis of natural products. Such method featured...
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Replacement of the CysA7-CysB7 disulfide bond with a 1,2,3-triazole linker causes unfolding in insulin glargine

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00160A, PaperMargaret A Brimble, Geoffrey Williams, Garth Cooper, Xun Little, Kathryn Lee
Two analogues of insulin glargine containing a 1,4-disubstituted 1,2,3-triazole group in place of the CysA7-CysB7 disulfide bond were prepared using CuAAC click chemistry to efficiently join the peptide chains. The...
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A novel synthetic chemistry approach to linkage-specific ubiquitin conjugation

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00130G, CommunicationRachel E. Morgan, Vijay Chudasama, Paul R. Moody, Mark E. B. Smith, S Caddick
Ubiquitination is of great importance as the post-translational modification of proteins with ubiquitin, or ubiquitin chains, facilitates a number of vital cellular processes. Herein we present a facile method of...
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Investigations into the decomposition of aminoacyl-substituted monosaccharide scaffolds from a drug discovery library

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00122F, PaperQi Qi He, Norbert Wimmer, Geraldine Verquin, Wim Meutermans, Vito Ferro
This study investigated the unexpected decomposition and associated intermediates of compound 1, a specific member of a drug discovery library based on a monosaccharide scaffold. LC/MS and NMR spectroscopic analyses...
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Pd-Catalyzed Asymmetric Allylic Amination Using Easily Accessible Metallocenyl P,N-Ligands

2 March, 2015 - 16:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C5OB00032G, PaperHongwei Wu, Fang Xie, Yanlan Wang, Xiaohu Zhao, Delong Liu, Wanbin Zhang
Compared to their C1-symmetric counterparts, planar chiral C2-symmetric metallocenyl P,N-ligands are efficient chiral ligands for Pd-catalyzed asymmetric allylic aminations, providing a number of amination products with high enantioselectivities. A non-C2-symmetric...
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