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Search for "inhibition" in Full Text gives 540 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

  • Ken-ichi Nakashima,
  • Junko Tomida,
  • Tomoe Tsuboi,
  • Yoshiaki Kawamura and
  • Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

Graphical Abstract
  • fungus; modified Mosher’s method; Muyocopron laterale; polyketides; Introduction Azaphilones, which are a class of fungal polyketides with diverse structures, have received growing attention due to their various biological activities, such as the inhibition of some protein–protein interactions [1][2
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Published 28 Aug 2020

Automated high-content imaging for cellular uptake, from the Schmuck cation to the latest cyclic oligochalcogenides

  • Rémi Martinent,
  • Javier López-Andarias,
  • Dimitri Moreau,
  • Yangyang Cheng,
  • Naomi Sakai and
  • Stefan Matile

Beilstein J. Org. Chem. 2020, 16, 2007–2016, doi:10.3762/bjoc.16.167

Graphical Abstract
  • an endosomal pathway. The low pKa value of the four GCP moieties could result in an improved buffering capacity, which could facilitate endosomal escape by the proton-sponge effect [28]. Significant inhibition of DNA transfection by bafilomycin (a macrolide antibiotic that can block the endosomal
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Published 14 Aug 2020

Stereoselective Biginelli-like reaction catalyzed by a chiral phosphoric acid bearing two hydroxy groups

  • Xiaoyun Hu,
  • Jianxin Guo,
  • Cui Wang,
  • Rui Zhang and
  • Victor Borovkov

Beilstein J. Org. Chem. 2020, 16, 1875–1880, doi:10.3762/bjoc.16.155

Graphical Abstract
  • activities [7][8]. For example, (S)-monastrol is 15-fold more effective in the inhibition of Eg 5 ATPase than its enantiomer, (R)-monastrol [9]. As more reports on the enantiospecific biological activity of DMPMs came to light, the development of an efficient and reliable asymmetric synthesis of enantiopure
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Published 31 Jul 2020

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

  • Dandan Li,
  • Enjuro Harunari,
  • Tao Zhou,
  • Naoya Oku and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

Graphical Abstract
  • DMSO. The respiration of live cells was quantified by the measurement of the absorption at 540 nm by a microplate reader. The experiment was run in a triplicate, and the rates of the cell-growth inhibition at each concentration were plotted on a single logarithmic chart to deduce the GI50 values of the
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Published 29 Jul 2020

Synthesis, docking study and biological evaluation of ᴅ-fructofuranosyl and ᴅ-tagatofuranosyl sulfones as potential inhibitors of the mycobacterial galactan synthesis targeting the galactofuranosyltransferase GlfT2

  • Marek Baráth,
  • Jana Jakubčinová,
  • Zuzana Konyariková,
  • Stanislav Kozmon,
  • Katarína Mikušová and
  • Maroš Bella

Beilstein J. Org. Chem. 2020, 16, 1853–1862, doi:10.3762/bjoc.16.152

Graphical Abstract
  • substrate of mycobacterial galactofuranosyltransferase GlfT2 in the transition state, we evaluated these compounds by computational methods, as well as in an enzyme assay for the possible inhibition of the mycobacterial galactan biosynthesis. Our data show that despite favorable docking scores to the active
  • , it does have some advantages compared to the spectrophotometric GlfT2 assay [19]. Firstly, in the crude assay GlfT2 uses its natural acceptor, GL4, which could affect its activity and thus the outcome of the inhibition studies. Secondly, it allows to evaluate inhibition of the enzymes involved in GL4
  • production (WecA, WbbL, UGM, GlfT1; Supporting Information File 1, Figure S1) [6] by the tested compounds, which could indicate the unspecific effects. These cannot be precluded, especially if relatively high concentrations of the studied molecules are required for achieving substantial enzyme inhibition
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Published 27 Jul 2020

Et3N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

  • Dharmender Singh,
  • Vipin Kumar and
  • Virender Singh

Beilstein J. Org. Chem. 2020, 16, 1740–1753, doi:10.3762/bjoc.16.146

Graphical Abstract
  • a variety of biological activities such as anticancer [24], inhibition of tyrosine phosphatase 1B, antioxidant properties, etc. [25][26][27]. Due to their numerous applications, they have found diverse uses such as thioindigo-like dyes, photoresponsive devices, and photoswitchable biomolecules [28
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Published 20 Jul 2020

Synthesis of new dihydroberberine and tetrahydroberberine analogues and evaluation of their antiproliferative activity on NCI-H1975 cells

  • Giacomo Mari,
  • Lucia De Crescentini,
  • Serena Benedetti,
  • Francesco Palma,
  • Stefania Santeusanio and
  • Fabio Mantellini

Beilstein J. Org. Chem. 2020, 16, 1606–1616, doi:10.3762/bjoc.16.133

Graphical Abstract
  • constitute a severe limitation in the employ of BER [2][3][4]. To minimize these drawbacks, its isoquinoline portion was derivatized in positions 9 and 13 that are critical for topoisomerase inhibition and quadruplex structure binding [5][6][7][8]. The insertion of a phenyl group or a benzhydryl group linked
  • of tetrahydroberberine analogues with interesting biological properties. Indeed, the investigation on the antiproliferative effects highlighted the ability of some hydrazono-DHBERs and hydrazono-THBERs to induce a significant growth inhibition on the tested cancer cell line, which might deserve
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Published 06 Jul 2020

Antibacterial scalarane from Doriprismatica stellata nudibranchs (Gastropoda, Nudibranchia), egg ribbons, and their dietary sponge Spongia cf. agaricina (Demospongiae, Dictyoceratida)

  • Cora Hertzer,
  • Stefan Kehraus,
  • Nils Böhringer,
  • Fontje Kaligis,
  • Robert Bara,
  • Dirk Erpenbeck,
  • Gert Wörheide,
  • Till F. Schäberle,
  • Heike Wägele and
  • Gabriele M. König

Beilstein J. Org. Chem. 2020, 16, 1596–1605, doi:10.3762/bjoc.16.132

Graphical Abstract
  • sponge prey availability [41]. The isolated metabolites showed various biological activities, such as cytotoxicity, antimicrobial, antiviral and antitumor activities, inhibition of transactivation for the farnesoid X receptor, inhibition of mammalian phospholipase A2, and ichthyotoxicity against the
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Published 03 Jul 2020

A dynamic combinatorial library for biomimetic recognition of dipeptides in water

  • Florian Klepel and
  • Bart Jan Ravoo

Beilstein J. Org. Chem. 2020, 16, 1588–1595, doi:10.3762/bjoc.16.131

Graphical Abstract
  • for peptides can be powerful tools for labeling or inhibition. Finding those binding motifs, especially in water which competes for intermolecular H-bonds, poses an enormous challenge. A dynamic combinatorial library can be a powerful method to overcome this issue. We previously reported artificial
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Published 02 Jul 2020

4-Hydroxy-3-methyl-2(1H)-quinolone, originally discovered from a Brassicaceae plant, produced by a soil bacterium of the genus Burkholderia sp.: determination of a preferred tautomer and antioxidant activity

  • Dandan Li,
  • Naoya Oku,
  • Yukiko Shinozaki,
  • Yoichi Kurokawa and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1489–1494, doi:10.3762/bjoc.16.124

Graphical Abstract
  • the control reaction (Figure 3). Because the Fenton reaction catalyzed by Cu2+ was used to generate the hydroxy radicals, entrapment of Cu2+ by 1 was initially suspected as the mechanism of chemiluminescence inhibition. However, this speculation was ruled out by a titration experiment using Chrome
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Published 26 Jun 2020

One-step route to tricyclic fused 1,2,3,4-tetrahydroisoquinoline systems via the Castagnoli–Cushman protocol

  • Aleksandar Pashev,
  • Nikola Burdzhiev and
  • Elena Stanoeva

Beilstein J. Org. Chem. 2020, 16, 1456–1464, doi:10.3762/bjoc.16.121

Graphical Abstract
  • heterocycle is present in several alkaloids such as emetine (1) and related compounds, that exhibit biological activities such as glucosidase inhibition, anti-amoebic properties as well as activity against breast cancer cell lines [2]. Notable examples of synthetic compounds include the dipeptidyl peptidase
  • IV inhibitor carmegliptin (2, DPP IV) with potential for the treatment of type-II diabetes [3][4]. A comparative study on novel classes of anticancer drugs identified benzo[a]quinolizines 3 and 4 (Figure 1) to be useful for a specific inhibition of heat shock response in cancer cells, which strongly
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Published 24 Jun 2020

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

  • Abimelek Cortes-Pacheco,
  • María Adelina Jiménez-Arellanes,
  • Francisco José Palacios-Can,
  • José Antonio Valcarcel-Gamiño,
  • Rodrigo Said Razo-Hernández,
  • María del Carmen Juárez-Vázquez,
  • Adolfo López-Torres and
  • Oscar Abelardo Ramírez-Marroquín

Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108

Graphical Abstract
  • antiinflammatory activity of these compounds has been gaining attention. In our previous work, we synthesized and in vivo evaluated the bisphosphonic esters 1 and 2, finding a moderate edema inhibition upon oral and topical administration on BALB/c mice. Thus, in this work, the bioisosteric replacement of an amide
  • functional group for an ester afforded the new bisphosphonates 3–6, which had a moderate oral edema inhibition (25 mg/kg dose) and a significant topical antiinflammatory activity (2 mg/ear) on BALB/c mice, with 6 being the most active hit (55.9% edema inhibition), comparable to the positive control (55.5
  • % edema inhibition) on a TPA topical model. Next, to assess the acute toxicity of the synthesized derivatives, test animals were administered with 50–100 mg/kg of 3–6, respectively, by an oral route, and after 14 days, neither lethality nor a significative weight loss were observed. Finally, a structure
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Published 08 Jun 2020

Fluorinated phenylalanines: synthesis and pharmaceutical applications

  • Laila F. Awad and
  • Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

Graphical Abstract
  • developed evogliptin (185) and it is currently approved for use in South Korea [121][122][123]. LY2497282: Eli Lilly identified LY2497282 (186) as a potent and selective DPP-4 inhibitor, also for the treatment of type II diabetes. The inhibition of GLP-1 degradation by dipeptidyl peptidase IV (DPP-4) has
  • suggested, based on genetic studies, that a selective Nav1.7 inhibition, will produce robust inhibition of pain without significant side effects [134][135]. Conclusion In view of the increased significance of FAAs in the development of bioactive compounds, considerable efforts were dedicated to the
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Review
Published 15 May 2020

Fabclavine diversity in Xenorhabdus bacteria

  • Sebastian L. Wenski,
  • Harun Cimen,
  • Natalie Berghaus,
  • Sebastian W. Fuchs,
  • Selcuk Hazir and
  • Helge B. Bode

Beilstein J. Org. Chem. 2020, 16, 956–965, doi:10.3762/bjoc.16.84

Graphical Abstract
  • -free supernatant was filled into wells of agar plates, which were inoculated with the pathogenic bacteria. Subsequently, the diameters of the inhibition zones were measured after 48 h. As references, different kanamycin concentrations to generate comparable inhibition zones were used (Table S4
  • , Supporting Information File 1). All analyzed wild type strains showed inhibition zones against the selected pathogens. Additionally, a comparison of the induced and the non-induced promoter-exchange mutants confirmed that the main bioactivity of all strains strongly depends on the fabclavines (Table 3
  • previously [20]. Occurrence of the different fabclavine derivatives in the analyzed Xenorhabdus strains. The results are based on the MALDI–HRMS and MALDI–MS2 analyses shown in Figures S2–S29 (Supporting Information File 1). Inhibition zones of the wild type (WT) and promoter-exchange mutant strains (non-ind
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Published 07 May 2020

Aldehydes as powerful initiators for photochemical transformations

  • Maria A. Theodoropoulou,
  • Nikolaos F. Nikitas and
  • Christoforos G. Kokotos

Beilstein J. Org. Chem. 2020, 16, 833–857, doi:10.3762/bjoc.16.76

Graphical Abstract
  • -anisaldehyde (98), which possessed a relatively long lifetime and an energetic value sufficient for C–X bond cleavage. The participation of the triplet state 4-anisaldehyde (98) in the reaction mechanism was also confirmed by the complete inhibition of the ATRA reaction in the presence of oxygen, a triplet
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Published 23 Apr 2020

Design and synthesis of diazine-based panobinostat analogues for HDAC8 inhibition

  • Sivaraman Balasubramaniam,
  • Sajith Vijayan,
  • Liam V. Goldman,
  • Xavier A. May,
  • Kyra Dodson,
  • Sweta Adhikari,
  • Fatima Rivas,
  • Davita L. Watkins and
  • Shana V. Stoddard

Beilstein J. Org. Chem. 2020, 16, 628–637, doi:10.3762/bjoc.16.59

Graphical Abstract
  • inhibition activities comparable to that of panobinostat. Multistep syntheses afforded the visualized targets TOI1, TOI2, TOI3-rev and TOI4 whose biological evaluation confirmed the strength of HDAC8 inhibition with TOI4 displaying the greatest efficacy at varying concentrations. The results of this study
  • development of novel HDAC inhibitors (HDACis) has become a rapidly evolving area where targeted inhibition has emerged in clinical research as a potential therapeutic approach for the treatment of various cancers as well as neurodegenerative disorders and immune related diseases [3][4][5]. Of specific
  • classified as highly potent amongst traditional HDACis [11]. According to previous reports, panobinostat not only induces apoptosis in cells, but also stimulates cell growth inhibition, and cell-cycle arrest in a time- and dose-dependent manner. Thus, panobinostat has demonstrated high therapeutic potential
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Published 07 Apr 2020

Opening up connectivity between documents, structures and bioactivity

  • Christopher Southan

Beilstein J. Org. Chem. 2020, 16, 596–606, doi:10.3762/bjoc.16.54

Graphical Abstract
  • 22833565 with 1040 Mw) has been annotated (even though the sodium salt is the active form in vivo). Note also that while formally “P” in the heparin case is SERPINC1 (ATIII) the mechanism is an indirect one involving the activation of binding to F2 (activated thrombin) for inhibition. Another problematic
  • example is mechanism-based covalent inhibition where the time dependence of IC50 for “A” is not captured. The structured capture of DARCLP by curation (or at least DARCP) has very high value from the additional relationships that can be explored via the entities and attributes as outlined below: Documents
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Published 02 Apr 2020

Photophysics and photochemistry of NIR absorbers derived from cyanines: key to new technologies based on chemistry 4.0

  • Bernd Strehmel,
  • Christian Schmitz,
  • Ceren Kütahya,
  • Yulian Pang,
  • Anke Drewitz and
  • Heinz Mustroph

Beilstein J. Org. Chem. 2020, 16, 415–444, doi:10.3762/bjoc.16.40

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  • cation radical Sens+• forms Sens back in the cycle. The system exhibited photocatalytic behavior with no big changes of absorption for 90 min under aerobic and anaerobic conditions. However, no polymerization occurred under air showing the inhibition of polymerization by oxygen [81]. This described
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Published 18 Mar 2020

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

  • Amit Raj Sharma,
  • Enjuro Harunari,
  • Naoya Oku,
  • Nobuyasu Matsuura,
  • Agus Trianto and
  • Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

Graphical Abstract
  • well. After incubating for 4 h at 37 °C, the medium was carefully removed by a suction aspirator, and formazan dye, formed by respiratory reduction by living cells, was quantified by the absorption at 450 nm, read by a microplate reader to calculate the rate of cell growth inhibition at each
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Published 02 Mar 2020

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

  • Man-Man Wang,
  • Hao Huang,
  • Lei Shu,
  • Jian-Min Liu,
  • Jian-Qiu Zhang,
  • Yi-Le Yan and
  • Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

Graphical Abstract
  • 2,4-D and the 1,3-dicarbonyl unit, we designed and synthesized a series of novel aryloxyacetic acid derivatives. In this context, these derivatives were subjected to HPPD inhibition, herbicidal activity, crop safety and structure–activity relationship (SAR) studies. As expected, many of the title
  • 13C NMR spectroscopy, and HRMS. Furthermore, the structures of compounds I18 and III4 were verified by X-ray diffractometry (Figure 3). Crystallographic data for crystalline I18 and III4 have been deposited with the Cambridge Crystallographic Data Centre (CCDC 1959130, CCDC 1959152). HPPD inhibition The
  • -withdrawing and electron-donating groups were introduced onto the benzene ring of I1, which significantly influenced the HPPD inhibition activity. We found that electron-withdrawing groups improve the activity; for example, I3 (Ki = 0.36 µM) and I4 (Ki = 0.59 µM) were more potent than I1 (Ki = 1.5 µM) and I2
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Published 19 Feb 2020

Potent hemithioindigo-based antimitotics photocontrol the microtubule cytoskeleton in cellulo

  • Alexander Sailer,
  • Franziska Ermer,
  • Yvonne Kraus,
  • Rebekkah Bingham,
  • Ferdinand H. Lutter,
  • Julia Ahlfeld and
  • Oliver Thorn-Seshold

Beilstein J. Org. Chem. 2020, 16, 125–134, doi:10.3762/bjoc.16.14

Graphical Abstract
  • assessment of HITub action We now determined to confirm the mechanism of action of the HITub compounds. To evaluate the biological mechanism of action behind the HITubs’ photoswitchable antimitotic activity, we first checked their inhibition of polymerisation of purified tubulin in a cell-free assay. The
  • results showed almost identical inhibition potency for HITub-4 at c = 10 μM as for the archetypal CDI colchicine at c = 20 μM (Figure S5, Supporting Information File 1), which we took to indicate that (Z)-HITub-4 exerted its bioactivity by specifically binding to tubulin directly in the cell-free system
  • photopharmaceutical tubulin inhibitors, as well as satisfactory photoswitchability of potency. We expect that due to the HITubs’ potency of tubulin inhibition, they will prove a powerful reagent system for biological studies on MT, especially where dark-isomer activity (compared to the currently known, lit-active
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Published 27 Jan 2020

Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose

  • Lukáš Kerner and
  • Paul Kosma

Beilstein J. Org. Chem. 2020, 16, 9–14, doi:10.3762/bjoc.16.2

Graphical Abstract
  • identified as a major mechanism contributing to antimicrobial resistance of Gram-negative pathogenic bacteria. Inhibition of the corresponding enzymatic steps, specifically the transfer of 4-amino-4-deoxy-ʟ-arabinose, would thus restore the activity of cationic antimicrobial peptides and several
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Published 02 Jan 2020

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

  • Soleiman E. Helaly,
  • Wilawan Kuephadungphan,
  • Patima Phainuphong,
  • Mahmoud A. A. Ibrahim,
  • Kanoksri Tasanathai,
  • Suchada Mongkolsamrit,
  • Janet Jennifer Luangsa-ard,
  • Souwalak Phongpaichit,
  • Vatcharin Rukachaisirikul and
  • Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

Graphical Abstract
  • beauverolide I (5) only exhibited slight inhibition toward the proliferation of the KB3.1 cell line, without either altered or dead cells observed (IC50 20 μg/mL). A number of compounds featuring a dihydrobenzofuran moiety, i.e., the core structure of glycoasperfuran (3), has been reported from endophytic [37
  • effects were further evaluated. Remarkably, the inhibition toward S. aureus and target cell lines was not observed in pigmentosin B (2), but only in pigmentosin A (1). Nevertheless, pigmentosin A (1) displayed anti-S. aureus activity independently from its antibiofilm activity. These properties qualified
  • for their ability to interfere in the biofilm formation of Staphylococcus aureus DSM1104 and Pseudomonas aeruginosa PA14 [51]. The biofilm inhibition assay was performed in 96-well microtiter plates using the microtiter dish biofilm formation assay described by O’Toole [52], with minor modifications
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Published 16 Dec 2019

Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A

  • Qiao Li,
  • Chen Zhuang,
  • Donghua Wang,
  • Wei Zhang,
  • Rongxuan Jia,
  • Fengxia Sun,
  • Yilin Zhang and
  • Yunfei Du

Beilstein J. Org. Chem. 2019, 15, 2958–2965, doi:10.3762/bjoc.15.291

Graphical Abstract
  • of the obtained chromone derivatives was their conversion to chromone-derived natural products. Frutinone A, isolated from the leaves and root bark of Polygala fruticosa, shows various biological activities, including antibacterial, antioxidant, and potent cytochrome P450 1A2 inhibition (CYP1A2, IC50
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Published 12 Dec 2019

Chemical synthesis of tripeptide thioesters for the biotechnological incorporation into the myxobacterial secondary metabolite argyrin via mutasynthesis

  • David C. B. Siebert,
  • Roman Sommer,
  • Domen Pogorevc,
  • Michael Hoffmann,
  • Silke C. Wenzel,
  • Rolf Müller and
  • Alexander Titz

Beilstein J. Org. Chem. 2019, 15, 2922–2929, doi:10.3762/bjoc.15.286

Graphical Abstract
  • myxobacterium Archangium gephyra (Figure 1) [5][6]. These cyclic peptides have interesting biological activities such as cytotoxic activity presumably via proteasome inhibition and immunomodulatory effects, and they also show good antibiotic effects against P. aeruginosa [7][8][9]. The structure–activity
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Published 05 Dec 2019
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