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Search for "similarity" in Full Text gives 289 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Azologization and repurposing of a hetero-stilbene-based kinase inhibitor: towards the design of photoswitchable sirtuin inhibitors

  • Christoph W. Grathwol,
  • Nathalie Wössner,
  • Sören Swyter,
  • Adam C. Smith,
  • Enrico Tapavicza,
  • Robert K. Hofstetter,
  • Anja Bodtke,
  • Manfred Jung and
  • Andreas Link

Beilstein J. Org. Chem. 2019, 15, 2170–2183, doi:10.3762/bjoc.15.214

Graphical Abstract
  • photoswitchable, compounds 4a and 4b were synthesized to test the influence of a rigid conformation around the C=C double bond on sirtuin inhibition. Interestingly, this increased rigidity provokes a complete loss of activity against Sirt1. Despite the fact, that all mammalian sirtuins possess profound similarity
  • the LC–HRMS, clearly confirming the experimentally found blue shift of 0.75 eV and 0.54 eV compared to compounds (E)-2b and (Z)-2b, respectively. Also here, we conclude that the calculations clearly support the formation of compounds 8a and/or 8b. However, due to the similarity of the spectra of 8a
  • and 8b, calculations do not allow to predict which of the two isomers was present in the respective fraction analysed. Regarding the high similarity between 8a/8b and selisistat, it was likely that these cyclized compounds could possess biological activity against sirtuins, too. On the other hand they
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Published 16 Sep 2019

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

  • Silvie Rimpelová,
  • Michal Jurášek,
  • Lucie Peterková,
  • Jiří Bejček,
  • Vojtěch Spiwok,
  • Miloš Majdl,
  • Michal Jirásko,
  • Miloš Buděšínský,
  • Juraj Harmatha,
  • Eva Kmoníčková,
  • Pavel Drašar and
  • Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

Graphical Abstract
  • of action are unknown. Therefore, based on the structural similarity between compound 1 and 2, we suspected that new interesting and relevant information on this biologically largely undescribed SL could be identified. In order to study the action of these commercially unavailable compounds
  • trilobolide (2), from the seeds of Laserpitium archangelica Wulfen, we extended the knowledge on the first one, so far almost undescribed. We revealed that despite a high degree of structural similarity with two cytotoxic SLs, compound 2 and thapsigargin, compound 1 exhibited cytotoxicity neither in the
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Published 13 Aug 2019

Halide metathesis in overdrive: mechanochemical synthesis of a heterometallic group 1 allyl complex

  • Ross F. Koby,
  • Nicholas R. Rightmire,
  • Nathan D. Schley,
  • Timothy P. Hanusa and
  • William W. Brennessel

Beilstein J. Org. Chem. 2019, 15, 1856–1863, doi:10.3762/bjoc.15.181

Graphical Abstract
  • that both [KA']∞ and [CsKA'2] display three such angles, two of which are relatively similar at ca. 135–140°, and a third that is substantially more bent (<120°) (see the Supporting Information File 1, Figure S2, for a visualization of the similarity). The significance of this is that [KA'] can be
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Published 02 Aug 2019

The cyclopropylcarbinyl route to γ-silyl carbocations

  • Xavier Creary

Beilstein J. Org. Chem. 2019, 15, 1769–1780, doi:10.3762/bjoc.15.170

Graphical Abstract
  • ]. The similarity of products formed from acetolysis of 32 and 42 implies that the same cation rearrangement manifold is involved. Scheme 9 gives a mechanistic rationale for these products. Capture of an unrearranged discrete cyclopropylcarbinyl cation 43 gives the major product 38, while migration of
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Published 24 Jul 2019

Fluorine-containing substituents: metabolism of the α,α-difluoroethyl thioether motif

  • Andrea Rodil,
  • Alexandra M. Z. Slawin,
  • Nawaf Al-Maharik,
  • Ren Tomita and
  • David O’Hagan

Beilstein J. Org. Chem. 2019, 15, 1441–1447, doi:10.3762/bjoc.15.144

Graphical Abstract
  • other areas of bioactives discovery research, to complement the widely used ROCF3 and RSCF3 groups and there is a clear similarity to the ‘polar lipophilic’ groups ROCF2H, and RSCF2H [26]. Experimental Microorganism growth Cunninghamella elegans DSM1908 was grown on Saboraud dextrose agar gel plates for
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Published 28 Jun 2019

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

  • Pierre-Olivier Schwartz,
  • Sebastian Förtsch,
  • Astrid Vogt,
  • Elena Mena-Osteritz and
  • Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

Graphical Abstract
  • waves in the cyclic voltammograms, the LUMO energy levels were calculated from Egopt and the HOMO energy and decrease with increasing amount of selenium atoms in the heterotriacenes. Because of the structural similarity of heterotriacenes 1–4 to 2,2’-bithiophene and 2,2’-biselenophene, which can be
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Published 24 Jun 2019

Catalytic asymmetric oxo-Diels–Alder reactions with chiral atropisomeric biphenyl diols

  • Chi-Tung Yeung,
  • Wesley Ting Kwok Chan,
  • Wai-Sum Lo,
  • Ga-Lai Law and
  • Wing-Tak Wong

Beilstein J. Org. Chem. 2019, 15, 955–962, doi:10.3762/bjoc.15.92

Graphical Abstract
  • supramolecular helices or dimers through intermolecular hydrogen bonding of two axially chiral biphenyl hybrid diols (1 and 2 in Scheme 1) which contain point chirality at the side arms and axial chirality at the biphenyl backbone [37]. We envisage the structural similarity and the ability of our scaffold to
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Published 18 Apr 2019

An efficient synthesis of the guaiane sesquiterpene (−)-isoguaiene by domino metathesis

  • Yuzhou Wang,
  • Ahmed F. Darweesh,
  • Patrick Zimdars and
  • Peter Metz

Beilstein J. Org. Chem. 2019, 15, 858–862, doi:10.3762/bjoc.15.83

Graphical Abstract
  • roots of Parthenium hysterophorus [5]. A recent enantioselective synthesis of (−)-isoguaiene (1) from (+)-dihydrocarvone [6] enabled an unambiguous assignment of its absolute configuration as depicted in Figure 1. Due to the structural similarity of 1 and the trisnorsesquiterpene clavukerin A (2), we
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Published 09 Apr 2019

Selective benzylic C–H monooxygenation mediated by iodine oxides

  • Kelsey B. LaMartina,
  • Haley K. Kuck,
  • Linda S. Oglesbee,
  • Asma Al-Odaini and
  • Nicholas C. Boaz

Beilstein J. Org. Chem. 2019, 15, 602–609, doi:10.3762/bjoc.15.55

Graphical Abstract
  • the use of a catalytic system using HNO3, dioxygen, iodine and NHPI in the acetoxylation of C–H bonds [47]. Given this similarity, we believe that the two systems are operating by similar mechanisms. In the Minisci system, a phthalimide N-oxyl (PINO) radical, which is formed by the oxidation of NHPI
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Published 05 Mar 2019

Computational characterization of enzyme-bound thiamin diphosphate reveals a surprisingly stable tricyclic state: implications for catalysis

  • Ferran Planas,
  • Michael J. McLeish and
  • Fahmi Himo

Beilstein J. Org. Chem. 2019, 15, 145–159, doi:10.3762/bjoc.15.15

Graphical Abstract
  • , albeit more indirect, comes from an inhibition study using omeprazole, which was predicted to possibly interact with ThDP-dependent enzymes. The prediction was based on the similarity of omeprazole to the tricyclic form of thiamin. This was confirmed experimentally when omeprazole was subsequently shown
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Published 16 Jan 2019

Synthesis, biophysical properties, and RNase H activity of 6’-difluoro[4.3.0]bicyclo-DNA

  • Sibylle Frei,
  • Adam K. Katolik and
  • Christian J. Leumann

Beilstein J. Org. Chem. 2019, 15, 79–88, doi:10.3762/bjoc.15.9

Graphical Abstract
  • opposite the modified part and 2’-O-methyl RNA flanks. The same construct was previously applied for the evaluation of 2’F-tc-ANA [35] and a similar one for CeNA [52]. For the assay E. coli RNase H was used due to its commercial availability and its similarity to the human enzyme [22]. The cleavage pattern
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Published 08 Jan 2019

Lectins of Mycobacterium tuberculosis – rarely studied proteins

  • Katharina Kolbe,
  • Sri Kumar Veleti,
  • Norbert Reiling and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

Graphical Abstract
  • products of Rv1753 and Rv2082 were reported to have 27% and 25% amino acid sequence similarity to the ALS1 gene from Candida albicans, which encodes the candida adhesin [78]. This lectin is cell surface-localized and mediates adherence of the fungus to endothelial and epithelial cells [86][87]. Fucose
  • Rv2082, and an associated ALS-like lectin function is only speculation. Mannose-sensitive hemagglutinin Two Mtb gene products, encoded by Rv2813 and Rv3659, were classified as MSHA-like proteins, with the highest amino acid similarity directed to MshM (41%) and MshE (26%), respectively, of the marine
  • homodimers, homotrimers, and higher-ordered oligomers, which increases their avidity for multivalent ligands. C-Type lectins play key roles in cell–cell interactions, such as host–pathogen interactions, and phagocytosis [92]. The Mtb gene product of Rv2075c shows partial amino acid sequence similarity to
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Published 02 Jan 2019

N-Acylated amino acid methyl esters from marine Roseobacter group bacteria

  • Hilke Bruns,
  • Lisa Ziesche,
  • Nargis Khakin Taniwal,
  • Laura Wolter,
  • Thorsten Brinkhoff,
  • Jennifer Herrmann,
  • Rolf Müller and
  • Stefan Schulz

Beilstein J. Org. Chem. 2018, 14, 2964–2973, doi:10.3762/bjoc.14.276

Graphical Abstract
  • and ESI mass spectra revealed fragmentation patterns helpful for the detection of similar compounds derived from other amino acids. Some of these compounds showed antimicrobial activity. The structural similarity of N-acylated amino acid methyl esters and similar lipophilicity to AHLs might indicate a
  • retention index for iso-C15:0 and anteiso-C15:0-NAME are Ic = 2352 and Ic = 2365, respectively, while all other methyl branch locations had a lower value. The close similarity of Inat = 2354 and Ic = 2352 suggested the methyl branch to be located in the iso-position. Consequently, iso-C15:0-NAME (6) was
  • against E. coli TolC, and it was the only compound that showed moderate cytotoxicity on a human cancer cell line. The close similarity of NAMEs, NAVMEs, and NAGMEs to AHLs might indicate a function as signalling compounds, although experiments with NAMEs and AHL reporter assays did not reveal any activity
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Published 03 Dec 2018

The activity of indenylidene derivatives in olefin metathesis catalysts

  • Maria Voccia,
  • Steven P. Nolan,
  • Luigi Cavallo and
  • Albert Poater

Beilstein J. Org. Chem. 2018, 14, 2956–2963, doi:10.3762/bjoc.14.275

Graphical Abstract
  • 29.6% for SIMes-based catalysts 1, 3 and 5, respectively (see Figure 1). The same trend applies to the IMes-based catalysts 2, 4 and 6, with %VBur values of 30.0%, 29.7% and 29.6%, respectively. On the other hand, as expected since there is similarity in the part bonded to the metal [49], no
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Published 30 Nov 2018

Protein–protein interactions in bacteria: a promising and challenging avenue towards the discovery of new antibiotics

  • Laura Carro

Beilstein J. Org. Chem. 2018, 14, 2881–2896, doi:10.3762/bjoc.14.267

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  • was screened by X-ray crystallography leading to the identification of four fragment hits. In an attempt to improve their binding affinities, another library was searched for compounds displaying similarity to these initial hits. After a docking-based screening followed by a fluorescence polarization
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Published 21 Nov 2018

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

  • Jacqueline Pollini,
  • Valentina Bragoni and
  • Lukas J. Gooßen

Beilstein J. Org. Chem. 2018, 14, 2737–2744, doi:10.3762/bjoc.14.252

Graphical Abstract
  • are certainly drawbacks for larger scale production (Scheme 2) [27]. Due to the structural similarity of ginkgolic and anacardic acids, we believed that a particularly desirable synthesis of 2-hydroxy-6-tridecylbenzoic acid (3) would involve CNSL as the substrate basis. However, the functionalization
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Published 31 Oct 2018

Synthesis and biological evaluation of 1,2-disubstituted 4-quinolone analogues of Pseudonocardia sp. natural products

  • Stephen M. Geddis,
  • Teodora Coroama,
  • Suzanne Forrest,
  • James T. Hodgkinson,
  • Martin Welch and
  • David R. Spring

Beilstein J. Org. Chem. 2018, 14, 2680–2688, doi:10.3762/bjoc.14.245

Graphical Abstract
  • analogues was observed to inhibit production of the virulence factor pyocyanin in the human pathogen Pseudomonas aeruginosa, which may be a result of their similarity to the Pseudomonas quinolone signal (PQS) quorum sensing autoinducer. This provided new insights regarding the effect of N-substitution in
  • was noted for the compounds possessing a linear octanyl side chain. We speculate that this is due to the similarity to the heptanyl chain present in the native PQS ligand. This observation is highly intriguing, as HHQ (Figure 1), which differs from these analogues only by the lack of an N-substituent
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Published 19 Oct 2018

Non-native autoinducer analogs capable of modulating the SdiA quorum sensing receptor in Salmonella enterica serovar Typhimurium

  • Matthew J. Styles and
  • Helen E. Blackwell

Beilstein J. Org. Chem. 2018, 14, 2651–2664, doi:10.3762/bjoc.14.243

Graphical Abstract
  • correlation is interesting because sdiA is the descendent of a horizontal gene transfer of rhlR [63]. Indeed, the sequence of SdiA from Salmonella is 45% identical to RhlR, more than it is to LasR (27%), QscR (33%), TraR (23%), LuxR (27%), or CviR (32%) [21]. In further support of a possible similarity
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Published 17 Oct 2018

Targeting the Pseudomonas quinolone signal quorum sensing system for the discovery of novel anti-infective pathoblockers

  • Christian Schütz and
  • Martin Empting

Beilstein J. Org. Chem. 2018, 14, 2627–2645, doi:10.3762/bjoc.14.241

Graphical Abstract
  • similarity to the signal molecule synthase were investigated. Here, substrates of chalcone synthase CHS2 from Medicago sativa were tested for their ability to block PqsD function. Indeed, caffeic acid analogues, such as 15, were identified as hits and further characterized as channel blockers as described
  • before [59]. Further interesting starting points for the discovery of PqsD inhibitors have been provided by a dedicated screening campaign involving fragment-based hit discovery, in silico screening and a similarity-guided approach starting from FabH inhibitors [60]. The most potent hit 16 of this study
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Published 15 Oct 2018

Synthesis of 3-aminocoumarin-N-benzylpyridinium conjugates with nanomolar inhibitory activity against acetylcholinesterase

  • Nisachon Khunnawutmanotham,
  • Cherdchai Laongthipparos,
  • Patchreenart Saparpakorn,
  • Nitirat Chimnoi and
  • Supanna Techasakul

Beilstein J. Org. Chem. 2018, 14, 2545–2552, doi:10.3762/bjoc.14.231

Graphical Abstract
  • acetylcholinesterase complexed with donepezil (PDB code 4ey7) [18] retrieved from the Protein Data Bank was used in the study because of its high similarity (approximately 88% similarity), good resolution (at 2.35 Å) and ligand state with donepezil of Human AChE structure. Molecular docking of AChE via the GOLD v5.2.2
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Published 02 Oct 2018

The enzymes of microbial nicotine metabolism

  • Paul F. Fitzpatrick

Beilstein J. Org. Chem. 2018, 14, 2295–2307, doi:10.3762/bjoc.14.204

Graphical Abstract
  • predicted sequences of Kdha and Kdhb show significant similarity to the small and medium subunits of nicotine dehydrogenase, while that of Kdhc shows the highest similarity to chicken xanthine dehydrogenase. The spectral properties of the partially purified protein are consistent with 6
  • in (S)-nicotine to form N-methylmyosmine. The recent evidence that the product of the oxidation of 6-hydroxynicotine by LHNO and DHNO arises from oxidation of a carbon–nitrogen bond [18][24] and the similarity of the active sites of LHNO and NicA2 to that of MAO makes it much more likely that the
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Published 31 Aug 2018

Lanyamycin, a macrolide antibiotic from Sorangium cellulosum, strain Soce 481 (Myxobacteria)

  • Lucky S. Mulwa,
  • Rolf Jansen,
  • Dimas F. Praditya,
  • Kathrin I. Mohr,
  • Patrick W. Okanya,
  • Joachim Wink,
  • Eike Steinmann and
  • Marc Stadler

Beilstein J. Org. Chem. 2018, 14, 1554–1562, doi:10.3762/bjoc.14.132

Graphical Abstract
  • ]+ with high congruency of measured and calculated ion intensities while the [M + H]+ ion cluster was completely absent. In spite of their similarity, the lanyamycin epimers 1 and 2 could be separated by repeated RP-HPLC on Nucleodur Phenyl-Hexyl with an isocratic water/acetonitrile solvent system (52:48
  • other bafilomycin type antibiotics, show very little similarity in their structures. The typical α-methyl-β-hydroxy part of the bafilomycin side chain is absent in 1/2, which features a unique α-methylene group. However, both share a carbonyl function in δ-position to the macrolide, which often is
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Published 26 Jun 2018

Spectroelectrochemical studies on the effect of cations in the alkaline glycerol oxidation reaction over carbon nanotube-supported Pd nanoparticles

  • Dennis Hiltrop,
  • Steffen Cychy,
  • Karina Elumeeva,
  • Wolfgang Schuhmann and
  • Martin Muhler

Beilstein J. Org. Chem. 2018, 14, 1428–1435, doi:10.3762/bjoc.14.120

Graphical Abstract
  • structural similarity of the possible oxidation products makes the assignment of occurring IR bands to certain species challenging. Glycerol oxidation was studied over different catalytically active metals, such as Au [15], AuAg/C [16], Pt [17][18], Au/C [19][20], Pt/C [20][21], Pd/C [20], PdAu/C [22], PdNi
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Letter
Published 12 Jun 2018

Oligonucleotide analogues with cationic backbone linkages

  • Melissa Meng and
  • Christian Ducho

Beilstein J. Org. Chem. 2018, 14, 1293–1308, doi:10.3762/bjoc.14.111

Graphical Abstract
  • oligonucleotide was observed. Other types of oligonucleotides with aminoalkyl moieties as part of artificial internucleotide linkages have also been reported. With respect to their structural similarity to Letsinger's aminoalkyl phosphoramidate linkages, these variants are categorized as 'related systems' in this
  • retained base-pairing fidelity and improved cellular uptake have been reported for some oligonucleotides with structural similarity to Letsinger's first-generation aminoalkylated phosphoramidates. Bruice's guanidinium- and S-methylthiourea-linked systems have a pronounced tendency to form triple-helical
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Published 04 Jun 2018

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

  • Anna Czarnecka,
  • Emilia Kowalska,
  • Agnieszka Bodzioch,
  • Joanna Skalik,
  • Marek Koprowski,
  • Krzysztof Owsianik and
  • Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

Graphical Abstract
  • are to be expected. This task is additionally difficult to accomplish due to a chemical similarity of oxygen and sulfur, two neighboring heteroatoms from the main group VI of the periodic table. A longer atomic radius of sulfur than oxygen should make the C–S bond weaker and more reactive than the C–O
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Published 29 May 2018
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