Amino- and polyaminophthalazin-1(2H)-ones: synthesis, coordination properties, and biological activity

• Zbigniew Malinowski,
• Emilia Fornal,
• Agata Sumara,
• Renata Kontek,
• Karol Bukowski,
• Beata Pasternak,
• Dariusz Sroczyński,
• Joachim Kusz,
• Magdalena Małecka and
• Monika Nowak

Beilstein J. Org. Chem. 2021, 17, 558–568, doi:10.3762/bjoc.17.50

• complex 17 with atom numbering scheme. The anisotropic displacement parameters are shown at the 50% probability level. Determination of relative cell viability (% of control) in different cell lines (HT-29; PC-3 and L-929) treated with compounds 6d (1), 6b (2), 5d (3), 5c (4), 5g (5), 5f (6) using the MTT

Mesoionic tetrazolium-5-aminides: Synthesis, molecular and crystal structures, UV–vis spectra, and DFT calculations

• Vladislav A. Budevich,
• Sergei V. Voitekhovich,
• Alexander V. Zuraev,
• Vadim E. Matulis,
• Vitaly E. Matulis,
• Alexander S. Lyakhov,
• Ludmila S. Ivashkevich and
• Oleg A. Ivashkevich

Beilstein J. Org. Chem. 2021, 17, 385–395, doi:10.3762/bjoc.17.34

• derivatives. Molecules of compounds 8a, 10, 11a, and the bistetrazolium cation 9, with displacement ellipsoids drawn at the 50% probability level. The hydrogen atoms are shown as spheres of arbitrary radii. The atom numbering is done for the asymmetric unit. Experimental (a) and TD-tHCTHhyb/6-311+G(2d,p

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• . subtilis. The fact that suppression effects are only observable for these genera could presumably be caused by the higher overlap in the ecological niches, triggering competition for the same nutrients. Indeed, a higher phylogenetic and metabolic similarity between bacteria increases the probability of

Naphthalonitriles featuring efficient emission in solution and in the solid state

• Sidharth Thulaseedharan Nair Sailaja,
• Iván Maisuls,
• Jutta Kösters,
• Alexander Hepp,
• Andreas Faust,
• Jens Voskuhl and
• Cristian A. Strassert

Beilstein J. Org. Chem. 2020, 16, 2960–2970, doi:10.3762/bjoc.16.246

• applications or in the case of NMe2, as sensors of dielectric constants or water content. Molecular structure in the crystal of Me as obtained by X-ray diffractometric analysis. Thermal displacement ellipsoids are shown with 50% probability. Color code: black = carbon, grey = hydrogen and blue = nitrogen. A

Synthesis of purines and adenines containing the hexafluoroisopropyl group

• Viacheslav Petrov,
• Rebecca J. Dooley,
• Alexander A. Marchione,
• Elizabeth L. Diaz,
• Brittany S. Clem and
• William Marshall

Beilstein J. Org. Chem. 2020, 16, 2739–2748, doi:10.3762/bjoc.16.224

• drawn at 30% probability. Crystal structure of 7a, with the thermal ellipsoids drawn at 30% probability. Top: 19F NMR spectra of 3a acquired over a sample temperature range of 223–373 K. Left: Fitted plot of integrated intensity vs interpulse delay time from the experiment inverting the minor rotamer of

Comparative ligand structural analytics illustrated on variably glycosylated MUC1 antigen–antibody binding

• Christopher B. Barnett,
• Tharindu Senapathi and
• Kevin J. Naidoo

Beilstein J. Org. Chem. 2020, 16, 2540–2550, doi:10.3762/bjoc.16.206

• probability distribution gives the best indication of relevant regions. The fourth residue (Thr4) shows multimodal sampling in φ and a bimodal distribution in ψ, with conformers at (−100°, 0°) and (−60°, 130°) being preferred for the antigen (Figure 4E and F). However, when glycosylated the sampling of Thr is

• 3 of the peptide, aspartate, with a scatter plot showing the allowed φ–ψ regions highlighted in blue (A), and a probability density Ramachandran plot (B) for the antigen, and a scatter plot (C) and probability density Ramachandran plot (D) for the Tn-antigen. While the second row (E–H) illustrates

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

• Haruyasu Asahara,
• Minami Hiraishi and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2020, 16, 1830–1836, doi:10.3762/bjoc.16.150

• afford nitrophenol 5b, which eluted with hexane/ethyl acetate 8:2 (41.7 mg, 0.17 mmol, 34%) as yellow solid. When the other nitroalkenes 1c–f were used, the reaction was conducted in the same way. X-ray crystallography of the major isomer of 4a. The thermal ellipsoids indicate 50% probability. Resonance

Synthesis and highly efficient light-induced rearrangements of diphenylmethylene(2-benzo[b]thienyl)fulgides and fulgimides

• Vladimir P. Rybalkin,
• Sofiya Yu. Zmeeva,
• Lidiya L. Popova,
• Valerii V. Tkachev,
• Andrey N. Utenyshev,
• Olga Yu. Karlutova,
• Alexander D. Dubonosov,
• Vladimir A. Bren,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2020, 16, 1820–1829, doi:10.3762/bjoc.16.149

• structure of 3Z. Thermal ellipsoids are drawn on the 30% probability level. Selected bond lengths (Å): C(3)–C(4) = 1.476(2), С(4)=С(5) = 1.360(2), С(3)=С(14) = 1.356(2). Molecular structure of 3E. Thermal ellipsoids are drawn on the 30% probability level. Selected bond lengths (Å): C(3)–C(4) = 1.461(2), С(4

• fulgide 3Z in acetonitrile solution before (1) and after irradiation with light of 436 nm for 30 (2), 60 (3) and 100 (4) s (2.5 × 10−5 M, T = 293 K). Molecular structure of photoproduct cis-9C’. Thermal ellipsoids are drawn on the 30% probability level. Selected bond lengths (Å): С(5)–С(16) = 1.531(3), С

Clickable azide-functionalized bromoarylaldehydes – synthesis and photophysical characterization

• Dominik Göbel,
• Marius Friedrich,
• Enno Lork and
• Boris J. Nachtsheim

Beilstein J. Org. Chem. 2020, 16, 1683–1692, doi:10.3762/bjoc.16.139

• h, 91%; h) 1) DPPA, DBU, PhMe, 25 °C, 15 h; 2) NaN3, PhMe, 60 °C, 4 h, 87%; i) 1) MeOTf, CH2Cl2, 25 °C, 2.5 h; 2) NaBH4, THF/MeOH 4:1 v/v, 0 °C, 2.5 h; 3) oxalic acid, THF/H2O 4:1 v/v, 25 °C, 20 h, 86%. Overall yield to 5: 45% (8 steps). The molecular structure of 5 shows 50% probability ellipsoids

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• probability of charge recombinations [89]. Serpone et al. found that 85% of the photogeneration events resulted in a recombination after 10 ns of illuminating TiO2 particles [90]. This implies that higher irradiation intensity may hinder photocatalysis by increasing the charge carrier density and subsequently

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions

• Gui-Feng Kang and
• Gang Zhang

Beilstein J. Org. Chem. 2020, 16, 1447–1455, doi:10.3762/bjoc.16.120

• . Selected examples of triazinethione-containing bioactive compounds. X-ray structure of 6-(methylthio)-4-phenyl-3,4-dihydro-1,3,5-triazine-2(1H)-thione (6aa) with thermal ellipsoids at 50% probability (CCDC 1991859). Strategies for the synthesis of triazinethiones. Aldehyde substrate scope of three

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

• Carlos H. Escalante,
• Eder I. Martínez-Mora,
• Carlos Espinoza-Hicks,
• Alejandro A. Camacho-Dávila,
• Fernando R. Ramos-Morales,
• Francisco Delgado and
• Joaquín Tamariz

Beilstein J. Org. Chem. 2020, 16, 1320–1334, doi:10.3762/bjoc.16.113

• natural pyrrolizine- and isoindole-containing alkaloids. Structures of 9m (a) and 10m (b) as determined by single-crystal X-ray diffraction crystallography (ellipsoids at the 30% probability level). M06-2X/6-31+G(d,p) Optimized geometry for each of the SCs (a and d), TSs (b and e) and ADs (c and f) of the

Ferrocenyl-substituted tetrahydrothiophenes via formal [3 + 2]-cycloaddition reactions of ferrocenyl thioketones with donor–acceptor cyclopropanes

• Grzegorz Mlostoń,
• Mateusz Kowalczyk,
• André U. Augustin,
• Peter G. Jones and
• Daniel B. Werz

Beilstein J. Org. Chem. 2020, 16, 1288–1295, doi:10.3762/bjoc.16.109

• molecular structures of cis-9c and trans-9d drawn using 50% probability displacement ellipsoids. The terminology cis and trans referred to the relative orientation of Ph and Fc groups. Synthesis of spirotetrahydrothiophenes 3 via non-concerted [3 + 2]-cycloadditions of thiocarbonyl ylide 1 with electron

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

• ) database, which compares the molecular structure of test compounds vs a large training set of experimental bioactive or inactive compounds [21]. The results of the prediction are summarized as probability of activity (Pa) and probability of inactivity (Pi) values, both ranging from 0 to 1 (Figure 2), where

The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts

• Svetlana A. Kuznetsova,
• Alexander S. Gak,
• Yulia V. Nelyubina,
• Vladimir A. Larionov,
• Han Li,
• Michael North,
• Vladimir P. Zhereb,
• Alexander F. Smol'yakov,
• Artem O. Dmitrienko,
• Michael G. Medvedev,
• Igor S. Gerasimov,
• Ashot S. Saghyan and
• Yuri N. Belokon

Beilstein J. Org. Chem. 2020, 16, 1124–1134, doi:10.3762/bjoc.16.99

• frameworks could be tuned by varying the ratio of anion/cation multitopic components and the basicity of the cation component. View of the crystal structure of F-1 (F-1a phase), with representation of atoms by thermal ellipsoids at a 30% probability level. The hydrogen atoms, except for those in NH groups

• and solvate water molecules, were omitted for clarity. Only the labels of symmetry-independent heteroatoms are shown. View of the crystal structure of F-1 (F-1a’ phase), with representation of the atoms via thermal ellipsoids at a 30% probability level. The hydrogen atoms, except for those in NH

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• )-styryl)-5(4H)-oxazolones 2a–j used in this work and overall reaction scheme. Molecular drawing of the oxazolone 2c. Molecular drawing of cyclobutane ortho-palladated 4a. Ellipsoids are shown at the 50% probability level. Ortho-palladation of oxazolones 2 by treatment with Pd(OAc)2 and different

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• experimental 1H and 13C NMR data of 1 presented a higher chemical shift similarity to those for 1b and thereby the (S)-configuration was suggested for C-2. Indeed, the DP4+ analysis [25] gave 100% probability for structure 1b and 0.0% probability for structure 1a (Table S2, Supporting Information File 2). This

A simple and easy to perform synthetic route to functionalized thienyl bicyclo[3.2.1]octadienes

• Dragana Vuk,
• Irena Škorić,
• Valentina Milašinović,
• Krešimir Molčanov and
• Željko Marinić

Beilstein J. Org. Chem. 2020, 16, 1092–1099, doi:10.3762/bjoc.16.96

• -isomers of compounds 3–7. Molecular structure of compound trans-6. Displacement ellipsoids are drawn for the probability of 30% and hydrogen atoms are shown as spheres of arbitrary radii. Crystal packing of trans-6. (a) Chain parallel to [100] and (b) chain parallel to [010]. 1H NMR spectra (CDCl3) of

Synthesis and anticancer activity of bis(2-arylimidazo[1,2-a]pyridin-3-yl) selenides and diselenides: the copper-catalyzed tandem C–H selenation of 2-arylimidazo[1,2-a]pyridine with selenium

• Mio Matsumura,
• Tsutomu Takahashi,
• Hikari Yamauchi,
• Shunsuke Sakuma,
• Yukako Hayashi,
• Tadashi Hyodo,
• Tohru Obata,
• Kentaro Yamaguchi,
• Yasuyuki Fujiwara and
• Shuji Yasuike

Beilstein J. Org. Chem. 2020, 16, 1075–1083, doi:10.3762/bjoc.16.94

• mechanisms are currently underway in our group. Biologically active selenides and diselenides having heteroaryl groups. Ortep drawings of 2a (a and b) and 3a (c and d, thermal elipsoids indicate 50% probability). The synthesis of bis(2-arylimidazopyridin-3-yl) diselenides. Reaction conditions: 1 (2 mmol), Se

Synthesis of C₇₀-fragment buckybowls bearing alkoxy substituents

• Yumi Yakiyama,
• Shota Hishikawa and
• Hidehiro Sakurai

Beilstein J. Org. Chem. 2020, 16, 681–690, doi:10.3762/bjoc.16.66

• drawing of the crystallographically independent unit with thermal ellipsoid at 50% probability b) Packing structure viewed from the a axis and c) from the b axis. The dotted lines indicate; blue: π–π, grey: CH···π, red: CH···O interactions. In b) and c), hydrogen atoms which are not engaged in any

• colored ones are aromatic carbons. Crystal structure of 5b. a) ORTEP drawing of the crystallographically independent unit with thermal ellipsoid at 50% probability. b) Packing structure viewed from the b axis and c) from the a axis. The dotted lines indicate; grey: CH···π, red: CH···O interactions. In b

• ) and c), hydrogen atoms which are not engaged in any interactions and the contribution of the one enantiomer are omitted for clarity. Crystal structure of 5c. a) ORTEP drawing of the crystallographically independent unit with thermal ellipsoid at 50% probability b) Packing structure viewed from the b

Direct borylation of terrylene and quaterrylene

• Haruka Kano,
• Keiji Uehara,
• Kyohei Matsuo,
• Hironobu Hayashi,
• Hiroko Yamada and
• Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

• -bridging oligorylenes, d) bay-alkoxy oligorylenes, and e) tetra-tert-butyl oligorylenes. (Top) Single crystal X-ray structure of TB4. The thermal ellipsoids are scaled at 50% probability. (Bottom) Packing diagram of TB4. The solvent molecules are omitted for clarity. UV–vis absorption and fluorescence

Synthesis of triphenylene-fused phosphole oxides via C–H functionalizations

• Md. Shafiqur Rahman and
• Naohiko Yoshikai

Beilstein J. Org. Chem. 2020, 16, 524–529, doi:10.3762/bjoc.16.48

• benzo[b]phospholes accessible by the three-component assembly hold promise for further explorations inot novel π-extended phosphole derivatives. Examples of functional molecules based on π-extended phospholes. ORTEP drawings of compound 8a (thermal ellipsoids set at 50% probability). a) top view; b

Six-fold C–H borylation of hexa-peri-hexabenzocoronene

• Mai Nagase,
• Kenta Kato,
• Akiko Yagi,
• Yasutomo Segawa and
• Kenichiro Itami

Beilstein J. Org. Chem. 2020, 16, 391–397, doi:10.3762/bjoc.16.37

• 50% probability; all hydrogen atoms and solvent molecules (pentane) are omitted for clarity; gray: carbon; olive green: boron; red: oxygen. (b) Side view of 1. (c) Packing mode of 1. Photophysical properties of 1. (a) UV–vis absorption (solid lines) spectra, fluorescence (dotted line) spectrum

Synthesis and circularly polarized luminescence properties of BINOL-derived bisbenzofuro[2,3-b:3’,2’-e]pyridines (BBZFPys)

• Ryo Takishima,
• Yuji Nishii,
• Tomoaki Hinoue,
• Yoshitane Imai and
• Masahiro Miura

Beilstein J. Org. Chem. 2020, 16, 325–336, doi:10.3762/bjoc.16.32

• × 10−5 M) and in solid states (dispersed in Fomblin®). ORTEP drawings of 4b and 4c with 50% thermal probability. Hydrogen atoms and solvent molecules are omitted for clarity. Only major orientation of the disordered structure is displayed. The CCDC numbers are 1971471 for (R)-4b and 1971470 for (R)-4c

Absolute configurations of talaromycones A and B, α-diversonolic ester, and aspergillusone B from endophytic Talaromyces sp. ECN211

• Ken-ichi Nakashima,
• Junko Tomida,
• Takao Hirai,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 290–296, doi:10.3762/bjoc.16.28

• been deposited with the Cambridge Crystallographic Data Centre (CCDC 1952663). Structures of compounds 1–6. Key HMBC (blue arrows) and COSY (bold bonds) correlations in 1 and 2. a) ORTEP drawing of 1, with thermal ellipsoids indicating 50% probability. The atoms of the minor disordered component have

• been omitted for clarity. b) Electronic circular dichroism spectra of 1 (black solid line) and 2 (red dashed line). a) ORTEP drawing of 3, with thermal ellipsoids indicating 50% probability. b) Electronic circular dichroism spectra of 3 (black solid line) and 4 (red dashed line). a) ORTEP drawing of 5

• , with thermal ellipsoids indicating 50% probability. b) Electronic circular dichroism spectrum of 5. 1H (400 MHz) and 13C (100 MHz) NMR data for 1 and 2 in CDCl3. Supporting Information Supporting Information File 265: A phytogenic tree for ECN211 and related species and NMR spectra of 1 and 2