A cross-metathesis approach to novel pantothenamide derivatives

• Jinming Guan,
• Matthew Hachey,
• Lekha Puri,
• Vanessa Howieson,
• Kevin J. Saliba and
• Karine Auclair

Beilstein J. Org. Chem. 2016, 12, 963–968, doi:10.3762/bjoc.12.95

• the higher stability observed for 16 in blood, we expect this stereoselective synthetic route to find utility in accessing other new pantothenamide derivatives. Chemical structures of N-pentylpantothenamide (1) and of its methyl allyl derivative 2. Structure of Grubbs’ catalysts used in this study. In

Separation and identification of indene–C₇₀ bisadduct isomers

• Bolong Zhang,
• Jegadesan Subbiah,
• David J. Jones and
• Wallace W. H. Wong

Beilstein J. Org. Chem. 2016, 12, 903–911, doi:10.3762/bjoc.12.88

• serendipitous and surprising given the large number of chemical structures involved. It is noteworthy that there have been several studies on reducing the number of isomers in fullerene bisadduct materials using synthetic strategies and about the successful application in solar cell devices [18][19][20][21][22

Enantioselective carbenoid insertion into C(sp³)–H bonds

• J. V. Santiago and
• A. H. L. Machado

Beilstein J. Org. Chem. 2016, 12, 882–902, doi:10.3762/bjoc.12.87

• carbene, triplet carbene and carbenoids. Classification of the carbenoid intermediates by the electronic nature of the groups attached to the divalent carbene carbon. Chiral bis(oxazoline) ligands used in enantioselective copper carbenoid insertion. Chemical structures of complexes (R)-18 and (S)-18

Is conformation a fundamental descriptor in QSAR? A case for halogenated anesthetics

• Maria C. Guimarães,
• Mariene H. Duarte,
• Josué M. Silla and
• Matheus P. Freitas

Beilstein J. Org. Chem. 2016, 12, 760–768, doi:10.3762/bjoc.12.76

• stable minima (ruled by intramolecular interactions) do not necessarily coincide with the bioconformation (ruled by enzyme induced fit). Consequently, a QSAR model based on two-dimensional chemical structures was built and exhibited satisfactory modeling/prediction capability and interpretability, then

• useful for understanding the action mechanism of related drugs, as well as to drive the synthesis of new drug like compounds. Since the milestone work by Hansch and Fujita [1], a variety of MD´s have been developed to improve the correlation of chemical structures with bioactivity, ranging from

• requirements for drug development. Multivariate Image Analysis applied to QSAR (MIA-QSAR) is a genuine 2D method, since descriptors are pixels of molecular projections drawn as black and white wireframes [10] and, more recently, as colored 2D-images (chemical structures) with spheres representing atoms with

Art, auto-mechanics, and supramolecular chemistry. A merging of hobbies and career

• Eric V. Anslyn

Beilstein J. Org. Chem. 2016, 12, 362–376, doi:10.3762/bjoc.12.40

• functional models, it is not surprising that my career has focused on the creation of new molecular and supramolecular structures designed to execute a particular function or achieve a certain task. Further, while we all know “beauty is in the eye of the beholder”, many of our group’s chemical structures are

Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol

• Miriana Kfoury,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2016, 12, 29–42, doi:10.3762/bjoc.12.5

• presence of 10 mM of CD. The radical scavenging activity was expressed as Trolox equivalents TEAC (μmol Trolox/g of G) by using a Trolox calibration curve prepared for a concentration range of 2.5–25 μM. All analyses were done in triplicate. Chemical structures, logP values and molecular volumes (V) of

Physical properties and biological activities of hesperetin and naringenin in complex with methylated β-cyclodextrin

• Waratchada Sangpheak,
• Jintawee Kicuntod,
• Roswitha Schuster,
• Thanyada Rungrotmongkol,
• Peter Wolschann,
• Nawee Kungwan,
• Helmut Viernstein,
• Monika Mueller and
• Piamsook Pongsawasdi

Beilstein J. Org. Chem. 2015, 11, 2763–2773, doi:10.3762/bjoc.11.297

• beneficial biological properties, i.e., free radical scavenging activity [3], cardioprotective action [4], antibacterial and antiviral activities [5]. Two flavonoids in the class of flavanones, hesperetin and naringenin (chemical structures in Figure 1), can be extracted from citrus fruits such as lemon

Learning from the unexpected in life and DNA self-assembly

• Jennifer M. Heemstra

Beilstein J. Org. Chem. 2015, 11, 2713–2720, doi:10.3762/bjoc.11.292

• systems, subtle changes to the energetics of DNA assembly can have rather large effects on the position of equilibrium. We were fortunately able to overcome this challenge by replacing the Cy3 with a hexachlorofluorescein (HEX). HEX and FAM are spectrally orthogonal, but have similar chemical structures

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• dissolution profiles. Chemical structures of 2-methoxyestradiol (top) and the derivatised CDs DIMEB and TRIMEB (bottom). The mode of inclusion of 2ME in the DIMEB cavity (a), space-filling side view of the complex with the 2ME molecule in green (b) and cutaway view (c), location of the A-ring of 2ME

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• -triggered disassembly of the host–guest complex. b) Chemical structures of the building blocks used here. c) Binding of Fc by CD and subsequent dissociation upon oxidation of Fc. Hydrodynamic diameters, d, and zeta potentials, ζ, measured by DLS of SNPs prepared at increasing salt concentrations (0–0.2 M

Synthesis of constrained analogues of tryptophan

• Elisabetta Rossi,
• Valentina Pirovano,
• Marco Negrato,
• Giorgio Abbiati and
• Monica Dell’Acqua

Beilstein J. Org. Chem. 2015, 11, 1997–2006, doi:10.3762/bjoc.11.216

• naturally occurring or chemically synthesized non-proteinogenic amino acids are classified [1]. Chemically synthesized non-proteinogenic amino acids embody in principle a countless collection of assorted chemical structures and are mainly employed as they are or as scaffolds for pharmacologically active

Stereochemistry of ring-opening/cross metathesis reactions of exo- and endo-7-oxabicyclo[2.2.1]hept-5-ene-2-carbonitriles with allyl alcohol and allyl acetate

• Piotr Wałejko,
• Michał Dąbrowski,
• Lech Szczepaniak,
• Jacek W. Morzycki and
• Stanisław Witkowski

Beilstein J. Org. Chem. 2015, 11, 1893–1901, doi:10.3762/bjoc.11.204

• ” and H-2”, H-2 and H-3’, H-5 and H-1” Hz; J-resolved; 1H NMR (CDCl3) 3JH1’,H2’ = 11 Hz. RI: 1583 (tR = 34.92 min); TOF MS ES+ m/z [M + Na]+ 202; HRMS m/z: [M + Na]+ calcd for C12H15NO3Na 202.0844; found: 202.0850. Chemical structures of catalysts [Ru]1–6 used in this work. Representative GC

Ruthenium indenylidene “1^st generation” olefin metathesis catalysts containing triisopropyl phosphite

• Stefano Guidone,
• Fady Nahra,
• Alexandra M. Z. Slawin and
• Catherine S. J. Cazin

Beilstein J. Org. Chem. 2015, 11, 1520–1527, doi:10.3762/bjoc.11.166

• shorten or provide alternative synthetic pathways for the synthesis of natural products displaying complex chemical structures [5][6][7][8][9]. Ru-based pre-catalysts are known to be more air-, moisture- and functional-group tolerant compared to early transition metal complexes [10][11][12][13]. In

Synthesis and evaluation of the biostability and cell compatibility of novel conjugates of nucleobase, peptidic epitope, and saccharide

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum,
• Khalid Omar Al Footy,
• Khadija Omar Badahdah and
• Bing Xu

Beilstein J. Org. Chem. 2015, 11, 1352–1359, doi:10.3762/bjoc.11.145

• incorporation of peptidic epitopes into molecular conjugates that consist of a nucleobase, amino acids, and a saccharide for potentially developing new supramolecular biomaterials. Results and Discussion Molecular design Scheme 1 shows the chemical structures of the conjugates explored in this work. In the NAS

• different concentrations for 7 days. Cell viability of (A) HeLa and (B) PC12 cells incubated with 5 + 8 at different concentrations. Chemical structures of the conjugates (nucleobase–amino acids–saccharide (NAS)), and nucleopeptides (NA). The representative synthesis route of conjugates NAS (1, including

Synthesis of γ-hydroxypropyl P-chirogenic (±)-phosphorus oxide derivatives by regioselective ring-opening of oxaphospholane 2-oxide precursors

• Iris Binyamin,
• Shoval Meidan-Shani and
• Nissan Ashkenazi

Beilstein J. Org. Chem. 2015, 11, 1332–1339, doi:10.3762/bjoc.11.143

• once binded to metals which favor a six-membered ring geometry. Moreover, these compounds could be advantageously used in organocatalysis and are commonly embedded in inorganic or organic matrix for various heterogeneous applications. Chemical structures of 2-methoxy-1,3,2-dioxaphospholane 2-oxide (1

New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y₂) isolated from the South China Sea

• Senhua Chen,
• Zhaoming Liu,
• Yayue Liu,
• Yongjun Lu,
• Lei He and
• Zhigang She

Beilstein J. Org. Chem. 2015, 11, 1187–1193, doi:10.3762/bjoc.11.133

• . Chemical structures of 1–10. Selected HMBC (arrow) correlations of 1–3. 1H,1H COSY (bold) and selected HMBC (arrow) correlations of 7 and 9. Kinetic analysis of the inhibition of α-glucosidase by 2 (left) and 6 (right). 1H and 13C NMR spectroscopic data for compounds 1–3. 1H and 13C NMR spectroscopic data

New tris- and pentakis-fused donors containing extended tetrathiafulvalenes: New positive electrode materials for rechargeable batteries

• Shintaro Iwamoto,
• Yuu Inatomi,
• Daisuke Ogi,
• Satoshi Shibayama,
• Yukiko Murakami,
• Minami Kato,
• Kazuyuki Takahashi,
• Kazuyoshi Tanaka,
• Nobuhiko Hojo and
• Yohji Misaki

Beilstein J. Org. Chem. 2015, 11, 1136–1147, doi:10.3762/bjoc.11.128

• derivatives and higher homologues of 5, which are expected to exhibit higher charge–discharge performance than the materials described in this paper. Chemical structures of 1–9 and TTP. Molecular orbitals of 5a (trans isomer). Molecular orbitals of 6a (trans isomer). Molecular orbitals of 8a (trans isomer

Synthesis of novel N-cyclopentenyl-lactams using the Aubé reaction

• Madhuri V. Shinde,
• Rohini S. Ople,
• Ekta Sangtani,
• Rajesh Gonnade and
• D. Srinivasa Reddy

Beilstein J. Org. Chem. 2015, 11, 1060–1067, doi:10.3762/bjoc.11.119

• the production of a variety of chemical structures and generated new techniques in chemistry [5][6][7][8][9][10]. Additionally, it was applied to the synthesis of different natural products of biological importance [11][12][13][14][15]. In the Aubé reaction, an intermolecular reaction takes place

A hybrid electron donor comprising cyclopentadithiophene and dithiafulvenyl for dye-sensitized solar cells

• Gleb Sorohhov,
• Chenyi Yi,
• Michael Grätzel,
• Silvio Decurtins and
• Shi-Xia Liu

Beilstein J. Org. Chem. 2015, 11, 1052–1059, doi:10.3762/bjoc.11.118

• iodide (PMII; 1 M), iodine (60 mM), 4-tert-butylpyridine (0.5 M), and lithium perchlorate (0.1 M) in acetonitrile. Chemical structures of the target dyes 1 and 2. Cyclic voltammograms of 1 (blue line), 2 (red line) and 6 (black line) in CH2Cl2 (0.1 M Bu4NPF6; Pt working electrode; scan rate 100 mV s−1

Donor–acceptor type co-crystals of arylthio-substituted tetrathiafulvalenes and fullerenes

• Xiaofeng Lu,
• Jibin Sun,
• Shangxi Zhang,
• Longfei Ma,
• Lei Liu,
• Hui Qi,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 1043–1051, doi:10.3762/bjoc.11.117

• structure of 2·(C70)4·(PhCl)2. a) Interactions between C70 molecule A and 2; b) Interactions between C70 molecule B and 2. The blue and black dashed lines indicated the intermolecular C–S and C–C contacts, respectively. The hydrogen atoms are omitted for clarity. Chemical structures of Ar-S-TTFs 1–8

Copper ion salts of arylthiotetrathiafulvalenes: synthesis, structure diversity and magnetic properties

• Longfei Ma,
• Jibin Sun,
• Xiaofeng Lu,
• Shangxi Zhang,
• Hui Qi,
• Lei Liu,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 850–859, doi:10.3762/bjoc.11.95

• . Chemical structures of arylthio-substituted tetrathiafulvalenes (1–7). Electrochemical data of TTFs in this report.a Preparation, composition, yield, and appearance of the salts.a Selected bond lengths, calculated charge, and conformations of TTFs. Supporting Information Supporting Information File 347

Mono- and multilayers of molecular spoked carbazole wheels on graphite

• Stefan-S. Jester,
• A. Vikas Aggarwal,
• Daniel Kalle and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 2783–2788, doi:10.3762/bjoc.10.295

• behave as more or less rigid objects of certain sizes and shapes – depending on their chemical structures. In addition, the images provide insight into the multilayer growth of the molecular spoked wheels (MSWs), where the first adlayer acts as a template for the commensurate adsorption of molecules in

• polymer light emitting diodes [12]. The chemical structures of both compounds are shown in Figure 1. Their synthesis and characterization has been reported before [11]. Here, we present scanning tunnelling microscopy (STM) investigations of both compounds, aiming at an extended description of the observed

• calibration, was performed using the SPIP 5 (Image Metrology) software package. Chemical structures of precursor 1 and MSW 2. Hub, spokes, and rim units are shown in green, red, and blue colors, respectively. (a)–(d) STM images, a molecular, and a supramolecular model of 1 at the OA/HOPG interface. (a) STM

Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism

• Joscha Vollmeyer,
• Friederike Eberhagen,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2014, 10, 2774–2782, doi:10.3762/bjoc.10.294

• diether (3) strand. Rather, it is a result of the chemical structures of the backbones and extraannular side chains that is schematically represented in Figure 5a. Each naphthylene unit is 2,7-disubstituted to realize the 120° angle in the rigid macrocyclic backbone (Figure 3b), and carries additional

• (undecyl diether strand, 2), and a polar interior (tetraethylene glycol strand, 3). (a) Schematic structures. The bold lines represent the (identical) macrocycle backbones; the thin straight, dash-dotted, and dash-double-dotted lines indicate alkoxy side chains. (b) Chemical structures. (c) Molecular

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• -CD physical mixture, (g) HSPC/γ-CD complex, (h) PEG/γ-CD PPRX. (C) Effects of CDs on the entrapment ratio of DOX into LP or PEG-LP. (A) Chemical structures of DSPE and PEG-DSPE, (B) photographs of the γ-CD solutions after adding DOX/LP or DOX/PEG-LP, and (C) turbidity of the DOX/PEG-LP solution in

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• ] calculations were performed using wB97XD [63] functional with TZVP [64] basis set and SMD [65] solvent model implemented in Gaussian 09 [66]. Alkyl chains were shortened to methyl groups to lessen the computational cost. Chemical structures of DPP core 1 and BODIPY core 2. Cyclic voltammetry of 9 (black) and