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

• Supporting Information File 1. The chemical structures of all title compounds were confirmed by 1H and 13C NMR spectroscopic analyses and HRMS spectrometric analyses. X-ray diffraction Single crystals of compounds I18 and III4 were cultivated for structure validation. Compound I18 was recrystallized from a

• experiments were conducted at the rate of 150 g ai/ha. After 15 days, the final results of crop safety were evaluated with two duplicates per experiment (Table 3). Chemical structures of the commercial HPPD inhibitors. The design strategy of aryloxyacetic acid derivatives as HPPD inhibitors and simulate the

• chloroacetate, K2CO3, CH3CN, 65 °C; (d) K2CO3, H2O, 65 °C; (e) aqueous HCl solution (10%), rt; (f) substituted 1,3-cyclohexanediones, EDCI, DMAP, DCM, rt; (g) substituted 1,3-dimethyl-1H-pyrazol-5-ol, EDCI, DMAP, DCM, rt; (h) Et3N, acetone cyanohydrin, DCM, rt. Chemical structures of title compound I and their

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

• , and high-yielding synthesis of HITub-4. Chemical structures of HITubs. Key variations with respect to HITub-4 are highlighted in dashed boxes. Photocharacterisation of HITub-4. a) Photochemical and thermal isomerisation. b) UV–vis spectra after saturating illumination at λ = 450, 505, and 530 nm

The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

• Xiaodong Zhang,
• Jun Xie,
• Zhiling Xu,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

• shown that the release rates of the BALE–Q[8] complex is slower than that of BALE in artificial intestinal juice, but it is faster than BALE in artificial gastric juice. Our results provide a new approach and theoretical basis for the development and utilization of baicalein. Chemical structures of

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

• isolation of three new compounds (2, 3, and 6), together with three known metabolites (1, 4, and 5), as well as species-specific patterns of secondary metabolite production in Gibellula sp. and C. javanica. Their chemical structures were elucidated based on the interpretation of their NMR and HRMS data

• were applied. Chemical structures of the isolated compounds 1–6. Experimental and TDDFT-calculated ECD spectra of compounds 1 (A), 2 (B), and 3 (C) in MeOH. A) Selected COSY (bold bonds) and HMBC (red arrows) correlations for compounds 2 and 3. B) Partial view of the Mosher ester of pigmentosin B (2

• ), showing the shielding effect of the phenyl group of MTPA on the methyl (C-13′), C-3′, and C-4′ positions of 2. The ΔδSR values are shown. Chemical structures of selected, literature-known compounds that are related to this study. HPLC–UV–vis profiles (200–600 nm) generated from the culture filtrate

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

• ′-ethylcarbodiimide hydrochloride, IBCF: isobutyl chloroformate, NMM: N-methylmorpholine, PyBOP: (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate, SNAc: SCH2CH2NAc, TFFH: fluoro-N,N,N′,N′-tetramethylformamidinium hexafluorophosphate. Chemical structures of naturally occurring argyrins with potent

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• control, respectively. HPLC–UV chromatogram of the extract from fruiting bodies of Skeletocutis sp. (detection wavelength λ = 190–600 nm). Chemical structures of compounds 1–6. Inhibition Leu-AMC hydrolysis. a) c (ʟ-Leu-AMC) = 100 µM. b) c (ʟ-Leu-AMC) = 50 µM. 1H and 13C NMR data for 1 (in acetone-d6) and

Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides

• José Brango-Vanegas,
• Luan A. Martinho,
• Lucinda J. Bessa,
• Andreanne G. Vasconcelos,
• Alexandra Plácido,
• Alex L. Pereira,
• José R. S. A. Leite and
• Angelo H. L. Machado

Beilstein J. Org. Chem. 2019, 15, 2544–2551, doi:10.3762/bjoc.15.247

• ) circuit Agr (accessory gene regulator) [8][9][10][11]. Four native thiolactonic cyclopeptides, named autoinducing peptides (AIPs, Figure 1), were found to be the chemical signals for the QS circuit Agr. Their chemical structures are remarkably alike to solonamides, and the synthesis of new molecules

• sulfhydryl group to the electrophilic MBH residue. Spectral characterization of the chemical structures of the solonamide analogues 9 The compounds were characterized by one- and two-dimensional NMR spectroscopy, infrared spectroscopy (IR) and mass spectrometry. The high-resolution MS/MS analysis allowed the

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• compound 8. Chemical structures of compound 9. Chemical structures of compound 10, 11 and 12. Chemical structure of compound 13. Chemical structure of compound 15 including the sigma-connected TCNQ dimer. Chemical structure of compound 16 for the kinetic resolution of epoxides. Chemical structure of

Nanopatterns of arylene–alkynylene squares on graphite: self-sorting and intercalation

• Tristan J. Keller,
• Joshua Bahr,
• Kristin Gratzfeld,
• Nina Schönfelder,
• Marcin A. Majewski,
• Marcin Stępień,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2019, 15, 1848–1855, doi:10.3762/bjoc.15.180

• alkoxy-substituted kekulene and octulene derivatives. Chemical structures of the molecular squares 1a/b, the kekulene derivative 2, and octulene derivative 3 [27]. (a)–(c) Scanning tunneling microscopy images, (d)–(f) supramolecular models, and (g)–(l) schematic models of supramolecular nanopatterns of

Synthesis, photophysical and electrochemical properties of pyridine, pyrazine and triazine-based (D–π–)₂A fluorescent dyes

• Keiichi Imato,
• Toshiaki Enoki,
• Koji Uenaka and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2019, 15, 1712–1721, doi:10.3762/bjoc.15.167

• , 124.50, 124.79, 129.58, 130.62, 133.57, 139.41, 141.56, 142.95, 147.31, 148.55, 153.55, 167.62 ppm (one aromatic carbon signal was not observed due to overlapping resonances); HRMS–ESI (m/z): [M + H] + calcd. for C67H56N7S2, 1022.40331; found, 1022.40344. Chemical structures of the (D–π–)2A fluorescent

Host–guest interactions in nor-seco-cucurbit[10]uril: novel guest-dependent molecular recognition and stereoisomerism

• Xiaodong Zhang,
• Wei Wu,
• Zhu Tao and
• Xin-Long Ni

Beilstein J. Org. Chem. 2019, 15, 1705–1711, doi:10.3762/bjoc.15.166

• different concentrations in aqueous solution (pH 2.0) at 298 K. 1H NMR spectra of G2 (1.0 mmol, D2O, pD = 2.0) in the presence of different concentrations of host-1. Chemical structures of host-1, host-2, G1, and G2. Plausible diastereomers showing the fluorescence response of G2 with host-1. Thermodynamic

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• dichloromethane at room temperature (λex = 310 nm). b) Plot of fluorescence intensity versus TBA[AuCl4] concentration (10−96 µM). (a) Chemical structures of the reported tetralactam macrocycles with aromatic sidewalls; (b) synthetic procedure to 2,3-dibutoxynaphthalene-based tetralactam macrocycles. Numberings on

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• binds more strongly to the substrate (purple) than to the product (blue). (a) The chemical structure of GC5A and schematic illustration of the binding between the luminescent dye and GC5A. (b) Chemical structures of luminescent dyes employed in this work. Binding constants and binding stoichiometries of

Precious metal-free molecular machines for solar thermal energy storage

• Meglena I. Kandinska,
• Snejana M. Kitova,
• Vladimira S. Videva,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• Stanislav B. Baluschev,
• Silvia E. Angelova and
• Aleksey A. Vasilev

Beilstein J. Org. Chem. 2019, 15, 1096–1106, doi:10.3762/bjoc.15.106

• photoisomerization and a longer life time of the higher energy forms in comparison with the known analogs. The chemical structures of all dyes in the series were characterized by NMR, UV–vis, IR spectroscopy and elemental analysis. The steady-state photophysical properties of the dyes were elucidated. The stability

• precipitation from ethanol/ethyl acetate 1:3 was needed to obtain analytically pure target dyes 4a–d. The dyes 4a and 4c were previously described [18][21] and were used as reference compounds. To the best of our knowledge dyes 4b and 4d are new compounds. The chemical structures of all dyes from the series

Molecular recognition using tetralactam macrocycles with parallel aromatic sidewalls

• Dong-Hao Li and
• Bradley D. Smith

Beilstein J. Org. Chem. 2019, 15, 1086–1095, doi:10.3762/bjoc.15.105

• are omitted for clarity. Selected X-ray structures of [2]rotaxanes with tetralactam A as the surrounding macrocycle reported by groups led by Leigh, Smith, Cooke, and Berná [37][39][50][52][53][54][55][56]. (a) Chemical structures of squaraine, thiosquaraine, croconaine, and acene guests that can bind

• * level. Reprinted with permission from [24], copyright 2018, American Chemical Society. Chemical structures of a) acetylcholine chloride, 26+·Cl−, (b) trimethyl-p-cyanobenzylammonium chloride, 27+·Cl−, and calculated structures (semiempirical, PM7) of their complexes inside tetralactam B (X = CH, Z = t

• appended, anionic Z group. Adapted with permission from [71], copyright 2015, John Wiley and Sons. Chemical structures of the tetralactam host macrocycles that are covered by this review. Synthetic yields of [2]rotaxanes with different dumbbell-shaped templates and tetralactam A as the surrounding

Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction

• Razieh Navari,
• Saeed Balalaie,
• Saber Mehrparvar,
• Fatemeh Darvish,
• Frank Rominger,
• Fatima Hamdan and
• Sattar Mirzaie

Beilstein J. Org. Chem. 2019, 15, 874–880, doi:10.3762/bjoc.15.85

• products 5a–d were not formed. The reaction mechanism is shown in Scheme 2. The chemical structures of the products 5a–d are shown in Figure 4. Usually, to activate the nitrile group for cyclization reaction, the existence of Lewis acid, the addition of organolithium reagents or metal

Azologization of serotonin 5-HT₃ receptor antagonists

• Karin Rustler,
• Galyna Maleeva,
• Piotr Bregestovski and
• Burkhard König

Beilstein J. Org. Chem. 2019, 15, 780–788, doi:10.3762/bjoc.15.74

• 1990s, the range of highly selective and potent drugs expanded based on various chemical structures. Nevertheless, on-off-targeting of a pharmacophore’s activity with high spatiotemporal resolution as provided by photopharmacology remains an unsolved challenge bearing additionally the opportunity for

• restoration [53][54][55], the respiratory chain [56] and lipids [57][58]. Owing to the reported serotonin antagonists’ chemical structures, the use of azobenzene as photochromic scaffold in the presented work seemed axiomatic. Therefore, the primary design of our photochromic derivatives is based on the

LCST phase behavior of benzo-21-crown-7 with different alkyl chains

• Yan Deng,
• Xing Li,
• Qiao Zhang,
• Zheng Luo,
• Chengyou Han and
• Shengyi Dong

Beilstein J. Org. Chem. 2019, 15, 437–444, doi:10.3762/bjoc.15.38

• the hydrophobicity of the crown ethers, but also exert great effect on solubility; c) small modifications in the chemical structures can result in remarkable differences in thermo-responsiveness. The change from carbamate groups to urea groups leads to the quench of thermo-responsiveness of crown

• properties. Both linkers and tails are important for regulating the LCST phenomenon. The presence of hydrophobic tails has a greater influence on the solubility, but the nature of the linkers is more important for the LCST properties. Based on the analyses of the relationship between chemical structures and

• °C; f) 70 °C. Purple dots in spectra indicate the newly emergent peaks upon heating. Chemical structures of 3a–e and 5a–e, and the cartoon representation of LCST behavior. Synthetic routes and yields of 3a–e and 5a–e. Supporting Information Supporting Information File 44: Experimental

Syntheses and chemical properties of β-nicotinamide riboside and its analogues and derivatives

• Mikhail V. Makarov and
• Marie E. Migaud

Beilstein J. Org. Chem. 2019, 15, 401–430, doi:10.3762/bjoc.15.36

Olefin metathesis in multiblock copolymer synthesis

• Maria L. Gringolts,
• Yulia I. Denisova,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

• rather clear nowadays that the olefin-metathesis reaction is a versatile tool for the synthesis of multiblock copolymers with diverse chemical structures. Due to the rapid progress in the catalyst design for living polymerization, sequential ROMP has become a well-established method of obtaining

Fabrication of supramolecular cyclodextrin–fullerene nonwovens by electrospinning

• Hiroaki Yoshida,
• Ken Kikuta and
• Toshiyuki Kida

Beilstein J. Org. Chem. 2019, 15, 89–95, doi:10.3762/bjoc.15.10

• promising as an approach for fiber functionalization, the scope is limited to cases with 1:1 inclusion complexes and chemically modified CD. Fullerenes have been widely studied in the fields of chemistry and materials science because they have attractive chemical structures and good electron acceptor

Organometallic vs organic photoredox catalysts for photocuring reactions in the visible region

• Aude-Héloise Bonardi,
• Frédéric Dumur,
• Guillaume Noirbent,
• Jacques Lalevée and
• Didier Gigmes

Beilstein J. Org. Chem. 2018, 14, 3025–3046, doi:10.3762/bjoc.14.282

• cycles involved with iodonium salt and (A) (TMS)3SiH, (B) NVK and (C) EDB. Structures of additives involved in the photoredox catalytic cycles. Structures of photoredox metal-based catalysts. Photocatalytical cycle for the Ru complex. Structures of photoredox organocatalysts. Diversity of the chemical

• structures of photoredox organocatalysts. Structures of benchmarked monomers. Structure of the CARET additive. Photoredox catalysis mechanism of a visible light-mediated living radical polymerization. (Abbreviation: PC for photoredox catalyst, [PC]* the photoredox catalyst at its excited state, Pn the

Green synthesis of new chiral 1-(arylamino)imidazo[2,1-a]isoindole-2,5-diones from the corresponding α-amino acid arylhydrazides in aqueous medium

• Nadia Bouzayani,
• Jamil Kraїem,
• Sylvain Marque,
• Yakdhane Kacem,
• Abel Carlin-Sinclair,
• Jérôme Marrot and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2018, 14, 2923–2930, doi:10.3762/bjoc.14.271

• observed with a total trans-diastereoselectivity controlled by intramolecular hydrogen bonds. Chemical structures of analogues. NOEs correlation showing the stereochemistry of the compound 5a. X-ray crystal structure of 5f shown at the 30% probability level. Strategy for the formation of 1-(arylamino)-1H

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

• scanning fluorimetry (DSF) assay [80]. Regrettably, no data was presented on the chemical structures of these compounds or the antibacterial activity. Nevertheless, this study reinforces the usefulness of integrating biophysical techniques with HTS approaches in order to detect and investigate SSB protein

•  8) as a template, Rush et al. applied a shape-comparison program (rapid overlay of chemical structures, ROCS). This study led to the identification of three lead-like scaffolds among which compound 38 (Figure 8) was the most active with a Kd of 73.9 μM. In spite of the fact that this molecule was

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• , CCl3COOH, and CF3COOH) in hexane at 60 °C for 45–60 min was achieved and reported. The chemical structures of new -SO3H functionalized ILs were confirmed by IR, 1H NMR, 13C NMR, and elemental analyses data. The NMR spectra provided evidence for resonating structures of N,N-disulfotetramethylguanidinium