The chemical behavior of terminally tert-butylated polyolefins

• Dagmar Klein,
• Henning Hopf,
• Peter G. Jones,
• Ina Dix and
• Ralf Hänel

Beilstein J. Org. Chem. 2015, 11, 1246–1258, doi:10.3762/bjoc.11.139

• shown in Figure 6. The O–O bond length is 1.4755(12) Å, which corresponds well to the mean value of 1.480 Å obtained from the Cambridge Crystallographic Database [17] for similar ring systems (69 hits, 81 values; one severe outlier omitted). The six-membered ring has an approximate “sofa” conformation

Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

• Marcel Mirel Popa,
• Emilian Georgescu,
• Mino R. Caira,
• Florentina Georgescu,
• Constantin Draghici,
• Raluca Stan,
• Calin Deleanu and
• Florea Dumitrascu

Beilstein J. Org. Chem. 2015, 11, 1079–1088, doi:10.3762/bjoc.11.121

• π-stacking, with shortest ring centroid-to-centroid distances of 3.743 Å in 6 and 3.766 Å in 8. It was ascertained from a search of the Cambridge Structural Database [34] (CSD) that the crystal of 6 is isostructural with that of 4,4’-bipyrimidine as the trans-rotamer (CSD refcode SACPAN). This is

An intramolecular C–N cross-coupling of β-enaminones: a simple and efficient way to precursors of some alkaloids of Galipea officinalis

• Hana Doušová,
• Radim Horák,
• Zdeňka Růžičková and
• Petr Šimůnek

Beilstein J. Org. Chem. 2015, 11, 884–892, doi:10.3762/bjoc.11.99

• ). According to the literature [55], as well as the Cambridge Structural Database, there is a plethora of compounds with an intramolecular N–H···O=C contact like 1a; on the other hand, the family of structurally related 1,2-dihydroquinolines [56] and ethanones [57] is limited to only seven examples. In the

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

• Tor E. Kristensen

Beilstein J. Org. Chem. 2015, 11, 446–468, doi:10.3762/bjoc.11.51

• structure-adapted database searches will uncover such protected amino acid derivatives in abundance, with little effort involved. Part of the reason for the impulsive willingness to adopt protective group chemistry is most surely connected to the fact that only minor quantities of end material are required

The preparation of new functionalized [2.2]paracyclophane derivatives with N-containing functional groups

• Henning Hopf,
• Swaminathan Vijay Narayanan and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 437–445, doi:10.3762/bjoc.11.50

• ) displays no formal crystallographic inversion symmetry, but is approximately inversion-symmetric (rmsd 0.02 Å). Again, we have reported the structure of the corresponding pseudo-gem isomer [20]. A search of the Cambridge database [31] revealed, perhaps surprisingly, that there are only two other X-ray

Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• solid-state inclusion complexes between RSV and CDs, despite the fact that such complexes have strong potential for incorporation into tablets or capsules when formulated for medicinal use. A search of the Cambridge Crystallographic Database [10] revealed that no CD·RSV crystal structures have been

• is a robust motif, occurring in all three inclusion complexes described here. Furthermore, this motif is unique to the trans-resveratrol inclusion complexes described here: no analogous motifs were found on searching the Cambridge Structural Database [10]. It is also important to note that for the

Synthesis and characterization of a new photoinduced switchable β-cyclodextrin dimer

• Florian Hamon,
• Claire Blaszkiewicz,
• Marie Buchotte,
• Estelle Banaszak-Léonard,
• Hervé Bricout,
• Sébastien Tilloy,
• Eric Monflier,
• Christine Cézard,
• Laurent Bouteiller,
• Christophe Len and
• Florence Djedaini-Pilard

Beilstein J. Org. Chem. 2014, 10, 2874–2885, doi:10.3762/bjoc.10.304

• AmberTools 1.4 distribution, following the strategy and methodology previously established [45]. Except for the linker, the CD fragments were taken from the R.E.DD.B. database [46] under project F-85 (http://q4md-forcefieldtools.org/REDDB/). Both the linker fragment and the cation were defined and

Autonomous assembly of synthetic oligonucleotides built from an expanded DNA alphabet. Total synthesis of a gene encoding kanamycin resistance

• Kristen K. Merritt,
• Kevin M. Bradley,
• Daniel Hutter,
• Mariko F. Matsuura,
• Diane J. Rowold and
• Steven A. Benner

Beilstein J. Org. Chem. 2014, 10, 2348–2360, doi:10.3762/bjoc.10.245

• database (NCBI). Using the OligArch software designed for this purpose [21], a gene that encodes the protein was constructed to be assembled from 20 single-stranded DNA fragments containing two, three, or four S (2’-deoxy-5-methylisocytidine) and B (2’-deoxyisoguanosine) nucleotides at their 5’ and 3’ ends

An experimental and theoretical NMR study of NH-benzimidazoles in solution and in the solid state: proton transfer and tautomerism

• Carla I. Nieto,
• Pilar Cabildo,
• M. Ángeles García,
• Rosa M. Claramunt,
• Ibon Alkorta and
• José Elguero

Beilstein J. Org. Chem. 2014, 10, 1620–1629, doi:10.3762/bjoc.10.168

• Database (refcode: ZAQRIU01) [4][26]. There are two independent molecules and in one of them, the CF3 is disordered (Figure 5). The most probable explanation of the splittings of Figure 4 is the existence of two independent molecules, a fact that is well documented in the literature [27][28][29][30]. We

Streptopyridines, volatile pyridine alkaloids produced by Streptomyces sp. FORM5

• Ulrike Groenhagen,
• Michael Maczka,
• Jeroen S. Dickschat and
• Stefan Schulz

Beilstein J. Org. Chem. 2014, 10, 1421–1432, doi:10.3762/bjoc.10.146

• series of n-alkanes (C8–C32). Compounds were identified by comparison of mass spectra to database spectra (Wiley 7, NIST 08 and our own created from synthesized reference compounds), by comparison of the retention index data to standards (own database and NIST Chemistry WebBook (2013) [14]) and by

Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide

• Richard J. Ingham,
• Claudio Battilocchio,
• Joel M. Hawkins and
• Steven V. Ley

Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56

• database for medicinal chemistry. For example, piperazine-2-carboxamide (1, Figure 2a) is an amino acid derivative with interesting biological properties [17]. At the time of writing, racemic 1 was identified as a notably expensive building block [18] and thus a good target for this transformation. We have

The regulation and biosynthesis of antimycins

• Ryan F. Seipke and
• Matthew I. Hutchings

Beilstein J. Org. Chem. 2013, 9, 2556–2563, doi:10.3762/bjoc.9.290

• (Figure 2). This sigma factor appears to be unique to the 14 known ant clusters in the database and they form a new sub-family of ECF sigma factors (Figure 4). Expression of the antFG and antHIJKLMNO genes is completely dependent on σAntA and over-expression of antA results in antFGHIJKLMNO expression in

Structure of 1,5-benzodiazepinones in the solid state and in solution: Effect of the fluorination in the six-membered ring

• Marta Pérez-Torralba,
• Rosa M. Claramunt,
• M. Ángeles García,
• Concepción López,
• M. Carmen Torralba,
• M. Rosario Torres,
• Ibon Alkorta and
• José Elguero

Beilstein J. Org. Chem. 2013, 9, 2156–2167, doi:10.3762/bjoc.9.253

• conditions afforded 6,7,8,9-tetrafluoro-1,4-dimethyl-1,3-dihydro-2H-1,5-benzodiazepin-2-one (2) in 80% yield. Geometries The geometries of two related structures together with their codes as reported in the Cambridge Structural Database [8][9] are shown in Figure 2. Compound 1 crystallizes in the monoclinic

Activation of cryptic metabolite production through gene disruption: Dimethyl furan-2,4-dicarboxylate produced by Streptomyces sahachiroi

• Dinesh Simkhada,
• Huitu Zhang,
• Shogo Mori,
• Howard Williams and
• Coran M. H. Watanabe

Beilstein J. Org. Chem. 2013, 9, 1768–1773, doi:10.3762/bjoc.9.205

• –MS fragmentation of the compound matched that provided in the Ultra GC–DSQ (ThermoElectron, Waltham, MA) GC–MS database. The structure of the compound was determined by NMR analysis in CDCl3 (Table 1). The presence of two O-CH3 groups at C-2’ (δc 51.99, δH 3.94) and C-2” (δc 52.31, δH 3.88) and

Lanostane- and cycloartane-type triterpenoids from Abies balsamea oleoresin

• Serge Lavoie,
• Charles Gauthier,
• Jean Legault,
• Sylvain Mercier,
• Vakhtang Mshvildadze and
• André Pichette

Beilstein J. Org. Chem. 2013, 9, 1333–1339, doi:10.3762/bjoc.9.150

• assessment. The photograph from our graphical abstract is from Robert H. Mohlenbrock @ USDA-NRCS PLANTS Database / USDA NRCS. 1995. Northeast wetland flora: Field office guide to plant species. Northeast National Technical Center, Chester.

Host–guest complexes of mixed glycol-bipyridine cryptands: prediction of ion selectivity by quantum chemical calculations, part V

• Svetlana Begel,
• Ralph Puchta and
• Rudi van Eldik

Beilstein J. Org. Chem. 2013, 9, 1252–1268, doi:10.3762/bjoc.9.142

• topic. Here we discuss two hybrid cryptands between [2.2.2] and [bpy.bpy.bpy]. They are abbreviated as [2.2.bpy] and [2.bpy.bpy] and are presented in Figure 2. Results and Discussion Although as of spring 2013 more than 650 X-ray structures are listed in the Cambridge Structural Database for [2.2.2] and

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• compounds performed poorly, binding with higher affinity to blood proteins than to SOD1, suggesting that these compounds may have significant off-target activity [37]. Docking calculations were performed to model the inhibitors at the dimer interface and a database of small molecules was screened to

A computational study of base-catalyzed reactions of cyclic 1,2-diones: cyclobutane-1,2-dione

• Nargis Sultana and
• Walter M. F. Fabian

Beilstein J. Org. Chem. 2013, 9, 594–601, doi:10.3762/bjoc.9.64

• ] basis sets, were used, respectively. Initial coordinates for [OH(H2O)4]– were taken from the WATER27 subset of the GMTKN30 database [40][41] and reoptimized with M06-2X/6-31+G(d,p). [OH(H2O)4]– was then placed about 6 Å above 1·(H2O)2 and the combined system again optimized, resulting in the ion-dipole

Synthesis of 5-(ethylsulfonyl)-2-methoxyaniline: An important pharmacological fragment of VEGFR2 and other inhibitors

• Miroslav Murár,
• Gabriela Addová and
• Andrej Boháč

Beilstein J. Org. Chem. 2013, 9, 173–179, doi:10.3762/bjoc.9.20

• collection) [8]. Nevertheless, compound 5 is cited in the database Reaxys (Reaxys Registry Number 783509, 37 reactions) and SciFinder Scholar database (CAS [5339-62-8], 191 reactions). In all cases, this compound was mentioned exclusively as a starting material or reactant [9]. Surprisingly the synthesis of

• mentioned only in the SciFinder database and originated from Bio-Rad Laboratories data collection [9]. Considering the above situation, we decided to develop a smart synthesis of substituted aniline 5 from available starting materials and determine all of the important physicochemical characteristics of the

• arylsulfonyl chloride 1 by treatment with Na2SO3, NaHCO3 at 65 °C in 98% yield [13] or in 67% yield [14]. Compound 2 has not been described. The physicochemical properties of compound 2 were not found in the SciFinder database. The Reaxys database contains its 1H NMR (300 MHz, CD3OD) [15] and IR spectra [16

The β-cyclodextrin/benzene complex and its hydrogen bonds – a theoretical study using molecular dynamics, quantum mechanics and COSMO-RS

• Jutta Erika Helga Köhler and
• Nicole Grczelschak-Mick

Beilstein J. Org. Chem. 2013, 9, 118–134, doi:10.3762/bjoc.9.15

• and were most different from the two O23l models, regardless of which orientation the hydrogen bonds had at the O6 rim. By the time these four empty β-CD models have been combined into one set of β-CD conformers and stored like this in the COSMO database, thermodynamic analysis with COSMOthermX will

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

• Dyanne L. Cruickshank,
• Natalia M. Rougier,
• Raquel V. Vico,
• Susan A. Bourne,
• Elba I. Buján,
• Mino R. Caira and
• Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117, doi:10.3762/bjoc.9.14

• in the Cambridge Crystallographic Database [15], which necessitated its ab initio structural solution by using direct methods. Density considerations indicated an asymmetric unit containing two complex molecules. In addition, prior to structural solution, a special feature was evident from the X-ray

Chemical–biological characterization of a cruzain inhibitor reveals a second target and a mammalian off-target

• Jonathan W. Choy,
• Clifford Bryant,
• Claudia M. Calvet,
• Patricia S. Doyle,
• Shamila S. Gunatilleke,
• Siegfried S. F. Leung,
• Kenny K. H. Ang,
• Steven Chen,
• Jiri Gut,
• Juan A. Oses-Prieto,
• Jonathan B. Johnston,
• Michelle R. Arkin,
• Alma L. Burlingame,
• Jack Taunton,
• Matthew P. Jacobson,
• James M. McKerrow,
• Larissa M. Podust and
• Adam R. Renslo

Beilstein J. Org. Chem. 2013, 9, 15–25, doi:10.3762/bjoc.9.3

• and MS/MS analysis using a hybrid linear ion-trap-Orbitrap mass spectrometer. Tandem mass spectra acquired were searched against the UniProtKb database employing ProteinProspector; four MS/MS spectra corresponding to the same peptide sequence were identified (Figure 7). This sequence was found to

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

• Laurie F. Mottram,
• Safiyyah Forbes,
• Brian D. Ackley and
• Blake R. Peterson

Beilstein J. Org. Chem. 2012, 8, 2156–2165, doi:10.3762/bjoc.8.243

• rhodamine (HRB, 9, and HR101, 10). Normalized absorbance (Panel A) and fluorescence emission (Panel B) spectra. Fluorophores were analyzed at 10 µM (absorbance) or 5 nM (fluorescence) in MeOH. The spectra for rhodamine 123 (4) in MeOH were downloaded from a publically accessible database [41]. Maximum

Synthesis of a library of tricyclic azepinoisoindolinones

• Bettina Miller,
• Shuli Mao,
• Kara M. George Rosenker,
• Joshua G. Pierce and
• Peter Wipf

Beilstein J. Org. Chem. 2012, 8, 1091–1097, doi:10.3762/bjoc.8.120

• these and other screening data disclosed for this series in the PubChem database that the tricyclic isoindolinone scaffolds hold strong potential for the development of selective and potent lead structures. Representative isoindolinone natural products and pharmaceuticals. X-Ray structure of epoxide 5

Synthesis and in silico screening of a library of β-carboline-containing compounds

• Kay M. Brummond,
• John R. Goodell,
• Matthew G. LaPorte,
• Lirong Wang and
• Xiang-Qun Xie

Beilstein J. Org. Chem. 2012, 8, 1048–1058, doi:10.3762/bjoc.8.117

• [16][17]. In this study, structural similarities were calculated between the compounds of the β-carboline library and the bioactive compounds in the well-annotated database, ChEMBL version 13, the largest publicly available compound-target database, containing 1,143,682 distinct compounds, 8,845

• database, and only β-carboline compounds with a Tc greater than 0.60 were considered for bioactivity analysis. A lower Tc threshold was used to identify a larger number of bioactivity targets. Table 4 lists the most promising bioactive targets for the newly synthesized β-carbolines together with the