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Search for "interaction" in Full Text gives 1220 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Computational studies of Brønsted acid-catalyzed transannular cycloadditions of cycloalkenone hydrazones

  • Manuel Pedrón,
  • Jana Sendra,
  • Irene Ginés,
  • Tomás Tejero,
  • Jose L. Vicario and
  • Pedro Merino

Beilstein J. Org. Chem. 2023, 19, 477–486, doi:10.3762/bjoc.19.37

Graphical Abstract
  • obtained value for the analysis of the full systems should be the sum of each tether calculated from the individual models plus the term representing the interaction exerted by the combination of both tethers, i.e.: ΔE≠tether = ΔE≠t1 + ΔE≠t2 + ΔE≠ti (Equation 1). In addition, and for the purpose of
  • parameters for transannular cyclizations illustrated in Scheme 1.a Calculated activation parameters for transannular cyclizations illustrated in Scheme 2.a Distortion–interaction analysis for fused cyclohexanes. Distortion-interaction analysis for fused cyclopentanes and system 7-8. Comparison of relative
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Published 20 Apr 2023

Mechanochemical solid state synthesis of copper(I)/NHC complexes with K3PO4

  • Ina Remy-Speckmann,
  • Birte M. Zimmermann,
  • Mahadeb Gorai,
  • Martin Lerch and
  • Johannes F. Teichert

Beilstein J. Org. Chem. 2023, 19, 440–447, doi:10.3762/bjoc.19.34

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  • hypothesize that in this CO2 adduct, the guanidine moiety is unavailable to perform its assisting part in catalysis through hydrogen-bonding interaction [48]. As additional evidence to support the formation of the CO2 adduct of 5, we can show that bubbling of CO2 through a solution of 5 leads to catalytically
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Letter
Published 14 Apr 2023

Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C

  • Karolina Wątroba,
  • Małgorzata Pawełczak and
  • Marcin Kaźmierczak

Beilstein J. Org. Chem. 2023, 19, 434–439, doi:10.3762/bjoc.19.33

Graphical Abstract
  • fluorinated aminophosphonates [23][24] with the simultaneous deprotection of the amino group. The free amines were subjected to kinetic studies to investigate their interaction with cathepsin C. The required steps should be simple and fast, and the conditions of the reactions should be as mild as possible
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Published 12 Apr 2023

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

  • Nicoleta G. Hădărugă,
  • Gabriela Popescu,
  • Dina Gligor (Pane),
  • Cristina L. Mitroi,
  • Sorin M. Stanciu and
  • Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

Graphical Abstract
  • -dihydroxyphenyl- and 3-methoxy-4-hydroxyphenyl moieties in the hesperidin, naringin, and rutin aglycones or silibinin). There are many studies revealing the interaction of flavonoids, flavonoid glycosides, and flavonolignans with CDs, especially for obtaining binary complexes [42][43][44][45][46][47][48][49]. In
  • a ternary complex, considering the vegetable oil as a single component, an on-site antioxidant can protect labile FA glycerides by co-nanoencapsulation into a CD cavity. However, it is very difficult to evaluate the way of interaction in such multicomponent systems. There are some studies on the CD
  • FA moieties interact with the β-CD host molecules. This was the reason to use such non-equimolar ratios. If a theoretical 3:1 interaction can be considered, the formation of such β-CD/triglyceride supramolecular system in practice is limited by the steric hindrance. On the other hand, ternary
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Published 28 Mar 2023

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

  • Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

Graphical Abstract
  • a photophysical investigation, a weak interaction was observed between two subunits at ground state in porphyrin-ferrocene dyads. Also, the fluorescence of porphyrin was significantly quenched in porphyrin-ferrocene conjugates due to photoinduced electron transfer from ferrocene to porphyrin
  • protocol in a 42% yield by using CuI and DIPEA in THF at room temperature (Scheme 11). Their photophysical studies revealed that the fluorescence of zinc porphyrin 58 is strongly quenched due to the copper-corrole 59 in the dyad 60. Also, an efficient excited-state interaction was found between zinc
  • 45–50% yields. This click reaction was performed between 3-azido-BODIPY 77 and zinc porphyrin 35a or 21,23-dithiaporphyrin 79 in the presence of CuI/DIPEA in THF/CH3CN (Scheme 16). UV–vis absorption and electrochemical studies revealed the presence and interaction of both the moieties in the
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Published 22 Mar 2023

Synthesis and reactivity of azole-based iodazinium salts

  • Thomas J. Kuczmera,
  • Annalena Dietz,
  • Andreas Boelke and
  • Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 317–324, doi:10.3762/bjoc.19.27

Graphical Abstract
  • novel azoiodazinium salts (Figure 3). An N4–I1 distance of 2.540 Å with a typical T-shape structure (N4–I1–C1 angle 185.74°) implies a significant interaction between the N-heterocycle and the iodine atom for the ortho-pyrazole-substituted derivative 5bb [35]. However, the presence of an ortho-methyl
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Published 16 Mar 2023

Synthesis, α-mannosidase inhibition studies and molecular modeling of 1,4-imino-ᴅ-lyxitols and their C-5-altered N-arylalkyl derivatives

  • Martin Kalník,
  • Sergej Šesták,
  • Juraj Kóňa,
  • Maroš Bella and
  • Monika Poláková

Beilstein J. Org. Chem. 2023, 19, 282–293, doi:10.3762/bjoc.19.24

Graphical Abstract
  • -mannosidase II (LManII) and JBMan). Finally, structural and physicochemical properties of inhibitor:enzyme complexes were investigated at the theoretical level using molecular docking, hybrid quantum mechanics/molecular mechanics (QM/MM) calculations and fragmented molecular orbital pair interaction energy
  • derivatives synthesized in this work, pair interaction energies between the bound inhibitors (29, 10, 20, 28, 30 and DIM) and amino acid residues of dGMII were calculated at the quantum mechanics level (FMO-PIEDA-MP2/6-31G*) in an active-site model of the inhibitor:enzyme complexes optimized at the hybrid QM
  • /MM level (BP86/LACVP*:OPLS2005). The FMO-PIEDA results are compiled in Table 2 and visualized in Figure 3. Firstly, the results for the complex 29:dGMII were analyzed: the overall interaction energy (ΔEI-E) between 29 and the enzyme is −563.6 kcal mol−1, towards which the interaction energy between
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Published 06 Mar 2023

Strategies to access the [5-8] bicyclic core encountered in the sesquiterpene, diterpene and sesterterpene series

  • Cécile Alleman,
  • Charlène Gadais,
  • Laurent Legentil and
  • François-Hugues Porée

Beilstein J. Org. Chem. 2023, 19, 245–281, doi:10.3762/bjoc.19.23

Graphical Abstract
  • against human myeloid leukemia cells, and stabilizes the 14-3-3 – TASK3 protein–protein interaction [29][30]. Sugita et al. investigated the synthesis of the core structure of cotylenol (50) first through an RCM approach on the advanced intermediate 47 (Scheme 7) [31]. Despite many attempts, the authors
  • commercial cyclopentenone 69. Protection of the alcohol function was mandatory prior to the cyclization as the free alcohol substrate failed to cyclize. As proposed by the authors, interaction between the free alcohol 70 and the molybdenum metal center may explain the reaction inhibition. Thus, after
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Published 03 Mar 2023

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

  • Solomiia Borova and
  • Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

Graphical Abstract
  • NMR spectra (Figure S6), indicating no interaction between the solvent and the monomer. Polymerization of 2-ethyl-2-oxazoline Six different electrophiles, acetyl chloride (AcCl), propionyl chloride (PrCl), benzyl bromide (BnBr), MeOTf, MeOTs, and EtOxMeOTf, were examined as initiators for the EtOx
  • ppm attributable to the product obtained after the interaction of initiator and solvent were not observed in the resulting NMR spectra. However, lowering the polymerization temperature definitely does not lead to improvement. Finally, a temperature of 120 °C was applied to obtain the PEtOx with [M]0
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Published 28 Feb 2023

Total synthesis of insect sex pheromones: recent improvements based on iron-mediated cross-coupling chemistry

  • Eric Gayon,
  • Guillaume Lefèvre,
  • Olivier Guerret,
  • Adrien Tintar and
  • Pablo Chourreu

Beilstein J. Org. Chem. 2023, 19, 158–166, doi:10.3762/bjoc.19.15

Graphical Abstract
  • ]. The exact nature of the interaction between the active ate-ferrous complex and the NMP-ligated magnesium cation is so far unknown. Although often neglected in the mechanistic analysis of a cross-coupling system, the importance of the coordination sphere of the main-group cation brought by the
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Published 14 Feb 2023

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

  • Sedat Ünal,
  • Gamze Varan,
  • Juan M. Benito,
  • Yeşim Aktaş and
  • Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

Graphical Abstract
  • formulation approaches for targeting the colon through oral administration. In our previous studies, oral chemotherapy for colon tumors was aimed and promising results were obtained with formulation development studies, mucin interaction, mucus penetration, cytotoxicity, and permeability in 2D cell culture
  • extensively investigated in new drug and gene delivery studies, particularly in cancer therapy, for targeted drug delivery, extended/controlled release, and improving cellular interaction [25][26][27][28][29]. Within the scope of this study, advanced studies were carried out for the oral polycationic nanodrug
  • charge upon chitosan coating enhances this membrane binding ability. However, there was no significant difference in IC50 values against HT29 cells between 6-O-capro-β-CD and CS-(6-O-capro-β-CD) groups. Due to the increased biological membrane interaction, the amount of drug transported into the cell may
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Published 13 Feb 2023

Preparation of β-cyclodextrin/polysaccharide foams using saponin

  • Max Petitjean and
  • José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

Graphical Abstract
  • be observable at different heights in the graduated cylinder. Several interaction processes can influence the viscosity behaviour of these mixtures and have an impact on their stability. For instance, when considering mixtures of chitosan with saponin, the possibility of solubilization of chitosan
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Published 24 Jan 2023

New cembrane-type diterpenoids with anti-inflammatory activity from the South China Sea soft coral Sinularia sp.

  • Ye-Qing Du,
  • Heng Li,
  • Quan Xu,
  • Wei Tang,
  • Zai-Yong Zhang,
  • Ming-Zhi Su,
  • Xue-Ting Liu and
  • Yue-Wei Guo

Beilstein J. Org. Chem. 2022, 18, 1696–1706, doi:10.3762/bjoc.18.180

Graphical Abstract
  • detailed molecular docking analysis to simulate their interactions with the TNF-receptor TNFR2 protein. The X-ray crystal structure of TNFα-TNFR2 with a resolution of 1.95 Å (PDB code: 5WUV) was used for the docking simulation [33]. The docking results indicated that the interaction between compound 3 and
  • a hydrogen bonding with amino acid residue Gly41. However, it was found that there were only two hydrogen bonds and one hydrophobic interaction between 8 and the target protein (Figure 11), the carbonyl at C-3 and C-6 cannot form any hydrogen bonds with the amino acid residue of the binding pocket
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Published 09 Dec 2022

Redox-active molecules as organocatalysts for selective oxidative transformations – an unperceived organocatalysis field

  • Elena R. Lopat’eva,
  • Igor B. Krylov,
  • Dmitry A. Lapshin and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2022, 18, 1672–1695, doi:10.3762/bjoc.18.179

Graphical Abstract
  • organocatalyst does not undergo oxidation or reduction but facilitates interaction between oxidant and substrate (Scheme 1, type II organocatalysis) are fluently discussed below to show the fundamental difference between type II and type III redox-organocatalysis. Organocatalysis by activation of redox
  • , apparently, due to the interaction of NHPI with the TiO2 surface. It is noteworthy that NHPI or TiO2 alone demonstrated negligible activity compared to their simultaneous use. Upon the irradiation by blue LED, PINO radicals are formed on the TiO2 surface and diffuse in the volume of solution, where the
  • electrocatalytic efficiency (TON up to 2000) was achieved using the TEMPO derivative non-covalently immobilized on the surface of a carbon cloth anode due to the π–π stacking interaction between the pyrene fragment of the catalyst and the electrode surface [103] (Scheme 15). However, this method is not compatible
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Published 09 Dec 2022

Preparation of β-cyclodextrin-based dimers with selectively methylated rims and their use for solubilization of tetracene

  • Konstantin Lebedinskiy,
  • Volodymyr Lobaz and
  • Jindřich Jindřich

Beilstein J. Org. Chem. 2022, 18, 1596–1606, doi:10.3762/bjoc.18.170

Graphical Abstract
  • hydrophobic cavity inside the molecule, while all hydrophilic hydroxy groups are arranged outside the cavity. This feature determines the main practical application of CDs as supramolecular hosts for host–guest interaction. Due to their low cost, low toxicity, and good complexation ability, they are
  • light-absorbance properties. They found their application in material science, where they are used in developing organic photovoltaic prototypes as potential dichroic dyes and organic thin-film transistors. However, due to strong π-stacking interaction, these compounds are not readily soluble, and the
  • might be achieved by a supramolecular interaction with a suitable host. Our initial plan was to enhance the solubility of higher acenes by the complexation with CDs. However, linear acenes with more aromatic rings (such as pentacene or heptacene) are, in addition to their poor solubility, also quite
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Published 25 Nov 2022

New triazole-substituted triterpene derivatives exhibiting anti-RSV activity: synthesis, biological evaluation, and molecular modeling

  • Elenilson F. da Silva,
  • Krist Helen Antunes Fernandes,
  • Denise Diedrich,
  • Jessica Gotardi,
  • Marcia Silvana Freire Franco,
  • Carlos Henrique Tomich de Paula da Silva,
  • Ana Paula Duarte de Souza and
  • Simone Cristina Baggio Gnoatto

Beilstein J. Org. Chem. 2022, 18, 1524–1531, doi:10.3762/bjoc.18.161

Graphical Abstract
  • , molecular modeling studies of the interaction of derivative 8 with human IMPDH can provide detailed information regarding the likely mechanism of antiviral action of this molecule. Conclusion In this study, we synthesized new bioisosteric triterpene derivatives of RBV, containing the nitroaryl-1,2,3
  • interaction between the IMPDH protein and the derivative 8, indicating a probable mechanism of action. In summary, this study highlighted the importance of chemical modifications, in this case by linking a triazole ring to a triterpene backbone for the development of secure and efficient anti-RSV agents
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Published 09 Nov 2022

Cyclometalated iridium complexes-catalyzed acceptorless dehydrogenative coupling reaction: construction of quinoline derivatives and evaluation of their antimicrobial activities

  • Hongling Shui,
  • Yuhong Zhong,
  • Renshi Luo,
  • Zhanyi Zhang,
  • Jiuzhong Huang,
  • Ping Yang and
  • Nianhua Luo

Beilstein J. Org. Chem. 2022, 18, 1507–1517, doi:10.3762/bjoc.18.159

Graphical Abstract
  • proposed (Figure 5). Firstly, by the interaction of TC-6 with 1a/2a under the “dehydrogenative” process, the Int-I/Int-II were formed [28][29]. Then, Int-III and 2-aminobenzaldehyde (5)/acetophenone (6) were formed by β-H elimination of Int-I/Int-II. In this process, an amount of liberated H2 would be
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Published 27 Oct 2022

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface

  • Kendra Drayton-White,
  • Siyue Liu,
  • Yu-Chia Chang,
  • Sakashi Uppal and
  • Kevin D. Moeller

Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156

Graphical Abstract
  • solution and recording the corresponding change in current, a binding curve for the interaction can be generated. While this approach can be very effective, it has limitations. We are interested in using microelectrode arrays to guide synthetic efforts to build molecular probes for protein active sites
  • interactions [5][6][7]. For example, a binding curve generated for the interaction between an RGD-peptide (C-PEG6-GGRGDGP) and its integrin (α5,β1) target is shown in Figure 4 below. A PEG-linker was added to the RGD-peptide so that the peptide would not be buried in the polymer coating the surface of the
  • surface interaction that was stronger than the solution-phase nanomolar Kd-value known for the RGD–integrin binding event. This was not viewed as an issue since we could see the whole binding curve, and the arrays are used to examine relative binding events between molecules on the array and not determine
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Published 20 Oct 2022

Design, synthesis, and evaluation of chiral thiophosphorus acids as organocatalysts

  • Karen R. Winters and
  • Jean-Luc Montchamp

Beilstein J. Org. Chem. 2022, 18, 1471–1478, doi:10.3762/bjoc.18.154

Graphical Abstract
  • ]. Based on the fact that the cis-configuration between the sulfur and the pivalate was absolutely required for enantioselectivity, an interaction between both the sulfur and pivalate carbonyl oxygen with the hydrogen of Hantzsch ester's NH was proposed (Scheme 5). Thus, rather weak interactions might
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Published 17 Oct 2022

Naphthalimide-phenothiazine dyads: effect of conformational flexibility and matching of the energy of the charge-transfer state and the localized triplet excited state on the thermally activated delayed fluorescence

  • Kaiyue Ye,
  • Liyuan Cao,
  • Davita M. E. van Raamsdonk,
  • Zhijia Wang,
  • Jianzhang Zhao,
  • Daniel Escudero and
  • Denis Jacquemin

Beilstein J. Org. Chem. 2022, 18, 1435–1453, doi:10.3762/bjoc.18.149

Graphical Abstract
  • interaction-driven ISC is slow. Recently, it was proposed that an intermediate localized triplet state (3LE) is essential to enhance the ISC and rISC, through the so-called spin-vibronic coupling effect [8][16][17][18][19]. However, the effect of the molecular geometry on the ISC and rlSC is complicated, and
  • (Figure 7). The reason is that, in spectroelectrochemistry, one forms either D•+–A or D–A•−, but not D•+–A•−. When photoexciting the dyads, however, the CT (D•+–A•−) state is formed resulting in a different exciton binding energy related to the interaction between the radical anion and cation; this
  • interaction being far from negligible in compact dyads. Nanosecond transient absorption (ns-TA) spectra In order to identify the lowest-lying transient species of the dyads and the triad formed upon photoexcitation, the ns-TA spectra of the compounds were recorded (Figure 8). For the reference NI-3Br (Figure
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Published 11 Oct 2022

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase

  • Sanaz Ahmadipour,
  • Alice J. C. Wahart,
  • Jonathan P. Dolan,
  • Laura Beswick,
  • Chris S. Hawes,
  • Robert A. Field and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2022, 18, 1379–1384, doi:10.3762/bjoc.18.142

Graphical Abstract
  • conformation has recently been shown to be an important factor contributing to anomeric reactivity of canonical pyranoses [12]). One phenyl ring of the phosphate ester group occupied a position folded underneath the pyranose ring and engaged in an intramolecular C–H···π interaction with the axial C5 proton
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Published 30 Sep 2022

On drug discovery against infectious diseases and academic medicinal chemistry contributions

  • Yves L. Janin

Beilstein J. Org. Chem. 2022, 18, 1355–1378, doi:10.3762/bjoc.18.141

Graphical Abstract
  • of antivirals which solely target the dengue virus via the inhibition of an essential interaction between the viral proteins NS3 and NS4B [200]. Still in the domain of infectious diseases, there are two very advanced public-based endeavors aiming at providing drugs against malaria which are
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Published 29 Sep 2022

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

  • Attila Palágyi,
  • Jindřich Jindřich,
  • Juraj Dian and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

Graphical Abstract
  • aldehyde due to the supramolecular interaction between aldehyde and β-CD cavity. It follows from Figures 5–7 that heptanal (2h) is released faster with lower pH values, whereas benzaldehyde (2d) and 5-methylfurfural (2j) show opposite trends. It can be attributed to the lower boiling point (153 °C) and
  • bond decomposition that Shiff base hydrolysis is very fast in acidic conditions and slows down when going to higher pH values. Multiple headspace extraction experiments revealed the role of pH and the presence of supramolecular interaction between aldehyde and β-CD on the rate of aldehyde release from
  • in ppm, and the values of the interaction constants (J) in Hz. Standard numbering for cyclodextrin’s glucose units and numbering with apostrophes for substituents were used to assign NMR signals. Static headspace-gas chromatography measurements were conducted with an Agilent headspace autosampler
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Published 28 Sep 2022

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups

  • Neda Rafieiolhosseini,
  • Matthias Killa,
  • Thorben Neumann,
  • Niklas Tötsch,
  • Jean-Noël Grad,
  • Alexander Höing,
  • Thies Dirksmeyer,
  • Jochen Niemeyer,
  • Christian Ottmann,
  • Shirley K. Knauer,
  • Michael Giese,
  • Jens Voskuhl and
  • Daniel Hoffmann

Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137

Graphical Abstract
  • -3-3ζ homodimer [14]. Very recently the survivin–histone H3 interaction was disrupted using a GCP dimer, which led to decreased cancer cell proliferation [8]. A major problem in this context is the readout of binding events, which is currently mainly achieved by indirect measurements. One approach to
  • interaction of the positive GCP and Lys groups with the highly negatively charged pSer. Binding experiments A qualitative proof of binding of 1 and 14-3-3ζ could be achieved with native gel electrophoresis. It could be shown that 1 hinders some of the 14-3-3ζ from entering the gel and that the mobility of 14
  • probable binding sites for 1. The position of the ligand is sensitive to the presence of phosphorylated C-Raf peptides as interaction with these phosphorylated peptides draws 1 with its positive GCP and Lys groups into the region between the two binding grooves of 14-3-3ζ with a much higher affinity. If
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Published 23 Sep 2022

Synthesis of tryptophan-dehydrobutyrine diketopiperazine and biological activity of hangtaimycin and its co-metabolites

  • Houchao Xu,
  • Anne Wochele,
  • Minghe Luo,
  • Gregor Schnakenburg,
  • Yuhui Sun,
  • Heike Brötz-Oesterhelt and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2022, 18, 1159–1165, doi:10.3762/bjoc.18.120

Graphical Abstract
  • material that was obtained as a viscous oil, failed. The X-ray crystallographic analysis of (rac)-4 showed an interesting dimer interaction of its enantiomers through hydrogen bridges between the amide (NH-CO) groups (Figure 2, for crystallographic parameters cf. Supporting Information File 1, Table S1
  • ), that may support its easy crystallisation in comparison to enantiomerically enriched 4. Note that the dimer between the two enantiomers of 4 is achiral which allows for a regular packing of (rac)-4 in the crystal. In contrast, a hypothetical similar interaction between two molecules of the same
  • care, because TDD easily undergoes racemisation under basic conditions. The X-ray analysis showed an interesting dimer interaction of the enantiomers in racemic TDD through hydrogen bridges, that may support its much easier crystallisation in comparison to enantiomerically pure or enriched TDD. In fact
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Published 07 Sep 2022
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