Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• article which covers almost all the unsuccessful as well as successful efforts towards the synthesis of sumanene and its congeners. The ball-and-stick representation, bowl fragments and the chemical structures of corannulene (1) and sumanene (2) are displayed in the Figure 1. 2 Synthesis of sumanene and

Synthesis of monophosphorylated lipid A precursors using 2-naphthylmethyl ether as a protecting group

• Jundi Xue,
• Ziyi Han,
• Gen Li,
• Khalisha A. Emmanuel,
• Cynthia L. McManus,
• Qiang Sui,
• Dongmian Ge,
• Qi Gao and
• Li Cai

Beilstein J. Org. Chem. 2020, 16, 1955–1962, doi:10.3762/bjoc.16.162

• the 4′-OH group. This work is currently underway in our lab. Chemical structures of hexa-acylated Escherichia coli lipid A, monophosphorylated lipid X (the reducing monosaccharide lipid A precursor), and disaccharide lipid A precursor (“disaccharide lipid X”). Enantioselective synthesis of Nap

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

• Giovanni Picca,
• Markus Probst,
• Simon M. Langenegger,
• Oleg Khorev,
• Peter Bütikofer,
• Anant K. Menon and
• Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

• , 74.06, 71.46, 71.38, 70.92, 67.64, 62.81, 62.76, 61.80, 56.17, 37.90, 37.83, 36.75, 29.30, 25.11, 19.68, 14.16; 31P NMR (121 MHz, DMSO-d6, δ) −2.86. Chemical structures of MPD and the three structural analogs MPC-1, MPC-2, and MPC-3. The molecular probes MPC-1 and MPC-3 are photoclickable derivatives

• , whereas the probe MPC-2 bears a fluorescent tag. Chemical structures of commercially available (S)-citronellol (Cit), 4,4′-dihydroxybenzophenone (BZP), ᴅ-mannose (Man), and 1,12-dodecanediol (Dod), the main starting materials in the synthesis of MPC-1 and MPC-2. The synthetic route leading to compounds

Synthesis of the tetrasaccharide repeating unit of the O-specific polysaccharide of Azospirillum doebereinerae type strain GSF71^T using linear and one-pot iterative glycosylations

• Arin Gucchait,
• Pradip Shit and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2020, 16, 1700–1705, doi:10.3762/bjoc.16.141

• strategies could provide access to large quantities of the oligosaccharides with defined chemical structures and free from biological impurities. Among the nineteen species of Azospirillum, Azospirillum doebereinerae was isolated from the rhizosphere of the biomass producing plant, Miscanthus giganteus [20

Models of necessity

• Timothy Clark and
• Martin G. Hicks

Beilstein J. Org. Chem. 2020, 16, 1649–1661, doi:10.3762/bjoc.16.137

• chemists represent chemical structures as two-dimensional sketches made up of atoms and bonds, simplifying the complex three-dimensional molecules comprising nuclei and electrons of the quantum mechanical description, is the everyday language of chemistry. This language uses models, particularly of bonding

• , that are not contained in the quantum mechanical description of chemical systems, but has been used to derive machine-readable formats for storing and manipulating chemical structures in digital computers. This language is fuzzy and varies from chemist to chemist but has been astonishingly successful

• and perhaps contributes with its fuzziness to the success of chemistry. It is this creative imagination of chemical structures that has been fundamental to the cognition of chemistry and has allowed thought experiments to take place. Within the everyday language, the model nature of these concepts is

Activated carbon as catalyst support: precursors, preparation, modification and characterization

• Melanie Iwanow,
• Tobias Gärtner,
• Volker Sieber and
• Burkhard König

Beilstein J. Org. Chem. 2020, 16, 1188–1202, doi:10.3762/bjoc.16.104

• ]. Fourier transmission infrared spectroscopy (FTIR): Activated carbon consists mainly of carbon atoms, besides different heteroatoms such as oxygen, hydrogen, nitrogen and sulfur. Thus, different functional groups govern the surface of the activated carbons and FTIR provides information on these chemical

• structures [65]. The spectra are usually recorded between 4000 cm−1 and 400 cm−1. The most characteristic bands of functional groups on the surface of the activated carbons are ≈3500, 1700, 1610, 1420 and 1140 cm−1 which indicate free or intermolecular bonded OH groups, carbonyl (C=O) stretching vibrations

Development of fluorinated benzils and bisbenzils as room-temperature phosphorescent molecules

• Shigeyuki Yamada,
• Takuya Higashida,
• Yizhou Wang,
• Masato Morita,
• Takuya Hosokai,
• Kaveendra Maduwantha,
• Kaveenga Rasika Koswattage and
• Tsutomu Konno

Beilstein J. Org. Chem. 2020, 16, 1154–1162, doi:10.3762/bjoc.16.102

• assist the development of environmentally benign, pure organic phosphorescent materials. (A) Transition-metal-containing and (B) pure organic phosphorescent materials reported thus far (bpy: 2,2'-bipyridine, ppy: 2-phenylpyridine, OEP: octaethylporphyrin). (A) Chemical structures of fluorescent bistolane

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• an electron acceptor in donor–acceptor systems [14]. The target compounds were obtained by nucleophilic substitution reaction of the intermediate quinazoline derivative Q1 with the corresponding donor compounds. The chemical structures were characterized by 1H NMR, 13C NMR, ATRIR spectroscopy and

• thin films of compounds 1–3 (λexc = 350 nm and PL decay curves (b) of thin films of derivatives 1–3 recorded at different emission wavelengths. Electron and hole NTOs of compounds 1–3 in the S1 excited state (vacuum). Chemical structures of exciplex-forming materials used, and visualization of white

Aryl-substituted acridanes as hosts for TADF-based OLEDs

• Naveen Masimukku,
• Dalius Gudeika,
• Oleksandr Bezvikonnyi,
• Ihor Syvorotka,
• Rasa Keruckiene,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 989–1000, doi:10.3762/bjoc.16.88

• presence of a palladium catalyst, with yields ranging from 27 to 50%. The chemical structures of 3–6 were confirmed by 1H and 13C NMR spectroscopy, elemental analysis and mass spectrometry. Transparent thin films of these compounds could be prepared by vacuum evaporation or by spin coating from solutions

Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches

• Rodrigo Costa e Silva,
• Luely Oliveira da Silva,
• Aloisio de Andrade Bartolomeu,
• Timothy John Brocksom and
• Kleber Thiago de Oliveira

Beilstein J. Org. Chem. 2020, 16, 917–955, doi:10.3762/bjoc.16.83

• electron and energy transfer. Chemical structures of the porphyrinoids and their absorption spectra: in bold are highlighted the 18 π aromatic system. Adapted from [7]. Photophysical and photochemical processes (Por = porphyrin). Adapted from [12][18]. Main dual photocatalysts and their oxidative/reductive

One-pot synthesis of dicyclopenta-fused peropyrene via a fourfold alkyne annulation

• Ji Ma,
• Yubin Fu,
• Junzhi Liu and
• Xinliang Feng

Beilstein J. Org. Chem. 2020, 16, 791–797, doi:10.3762/bjoc.16.72

• solution (10−5 M). Inset: photograph of a CH2Cl2 solution of 1. (b) Cyclic voltammogram of 1 (0.1 M n-Bu4NPF6 in DCM) at a scan rate of 50 mV s−1. Molecular orbitals of peropyrene derivative 6 and the dicyclopenta-fused peropyrene 1. Chemical structures of dicyclopenta-fused pyrene derivatives i–iii

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

• considering conformers at pH 7 to simulate the physiological conditions where the pH is 7.4. Results were analyzed in both Sybyl-X and UCSF Chimera. Chemical structures of the target diazine-based surrogates for the central core of panobinostat. Docking pose for panobinostat and panobinostat derivatives in

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

• ppm; HRMS (Spiral MALDI) m/z: [M]+ calcd for C66H56, 848.4377; found, 848.4377; UV–vis (toluene): λmax (ε [104 M−1 cm−1]) = 493 (1.8), 528 (4.9) and 572 (8.6) nm; fluorescence (toluene): λmax (λex = 489 nm) = 583, 629 and 682 nm. Chemical structures of a) oligorylene-bisimides, b) oligorylenes, c) bay

Opening up connectivity between documents, structures and bioactivity

• Christopher Southan

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

• . However, we will need to await the technical applicability in respect to DARCP capture to see if this opens up connectivity. Keywords: activity data; databases; drug discovery; chemical structures; protein targets; Introduction This article assesses a key aspect of data sharing that has the potential to

• . Connectivity: This term is used for an explicit link (e.g., a URL) between a published document and the chemical structures specified therein. Implicit is not only manual navigation (e.g., link-clicking) but also that such connectivity can be made machine-readable and thus computationally interrogated at large

Regioselectively α- and β-alkynylated BODIPY dyes via gold(I)-catalyzed direct C–H functionalization and their photophysical properties

• Takahide Shimada,
• Shigeki Mori,
• Masatoshi Ishida and
• Hiroyuki Furuta

Beilstein J. Org. Chem. 2020, 16, 587–595, doi:10.3762/bjoc.16.53

• novel functional fluorescent materials. (a) Chemical structures of BODIPY (1) and dipyrromethane (2). (b) C–C bond forming alkynylations of pyrrole and its derivatives by Sonogashira coupling and electrophilic alkynylation. (c) Peripheral alkynylated BODIPY derivatives (3–6) prepared in this work. TIPS

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

• ), were isolated from the culture broth of an actinomycete of the genus Micrococcus, which was associated with a stony coral, Catalaphyllia sp. Their chemical structures were elucidated by spectroscopic analysis including NMR and MS, with special assistance of spin system simulation studies for the

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