Fluorescent nucleobase analogues for base–base FRET in nucleic acids: synthesis, photophysics and applications

• Mattias Bood,
• Sangamesh Sarangamath,
• Moa S. Wranne,
• Morten Grøtli and
• L. Marcus Wilhelmsson

Beilstein J. Org. Chem. 2018, 14, 114–129, doi:10.3762/bjoc.14.7

• FBAs (see Figure 2 for chemical structures) include C8 to S8 thio-RNA analogue thA [23], the C8-naphtalene substituted adenines cnA and dnA [24], as well as our own quadracyclic qAN1 [25]. A handful of fluorescent guanine analogues has been synthesized and characterized and includes the recent turn-on

Halogen-containing thiazole orange analogues – new fluorogenic DNA stains

• Aleksey A. Vasilev,
• Meglena I. Kandinska,
• Stanimir S. Stoyanov,
• Stanislava B. Yordanova,
• David Sucunza,
• Juan J. Vaquero,
• Obis D. Castaño,
• Stanislav Baluschev and
• Silvia E. Angelova

Beilstein J. Org. Chem. 2017, 13, 2902–2914, doi:10.3762/bjoc.13.283

• .). Simulated TDPBE0 spectra in methanol. Electron density (isovalue = 0.002) mapped with electrostatic potential (color scheme: green for negative surface map values and blue for the positive ones). Chemical structures of TO and SYBR Green I – commercial monomethine fluorescent dsDNA binders. Synthesis of the

¹⁵N-Labelling and structure determination of adamantylated azolo-azines in solution

• Sergey L. Deev,
• Alexander S. Paramonov,
• Tatyana S. Shestakova,
• Igor A. Khalymbadzha,
• Oleg N. Chupakhin,
• Julia O. Subbotina,
• Oleg S. Eltsov,
• Pavel A. Slepukhin,
• Vladimir L. Rusinov,
• Alexander S. Arseniev and
• Zakhar O. Shenkarev

Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250

• Determining the accurate chemical structures of synthesized compounds is essential for biomedical studies and computer-assisted drug design. The unequivocal determination of N-adamantylation or N-arylation site(s) in nitrogen-rich heterocycles, characterized by a low density of hydrogen atoms, using NMR

• product structure were also found for N-arylation or N-alkylation with tert-butyl fragments in the series of 1,2,3-triazole [15][16], tetrazole [17][18][19][20], and purine [21] derivatives. Meanwhile, knowledge of the accurate chemical structures of N-substituted heterocycles is essential for biomedical

Novel approach to hydroxy-group-containing porous organic polymers from bisphenol A

• Tao Wang,
• Yan-Chao Zhao,
• Li-Min Zhang,
• Yi Cui,
• Chang-Shan Zhang and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 2131–2137, doi:10.3762/bjoc.13.211

• constructed ultimately. BPA and multi-formyl-containing compounds are suspended in o-dichlorobenzene, and TSA, as a catalyst, was then added into reaction system. After the reaction in a sealed tube at 180 °C for 72 h, three polymers PPOP-1–PPOP-3 were obtained. The possible chemical structures of the

Complexation of molecular clips containing fragments of diphenylglycoluril and benzocrown ethers with paraquat and its derivatives

• Leonid S. Kikot',
• Catherine Yu. Kulygina,
• Alexander Yu. Lyapunov,
• Svetlana V. Shishkina,
• Roman I. Zubatyuk,
• Tatiana Yu. Bogaschenko and
• Tatiana I. Kirichenko

Beilstein J. Org. Chem. 2017, 13, 2056–2067, doi:10.3762/bjoc.13.203

• , the studied clips form inclusion complexes of 1:1 composition. Chemical structures of hosts 1–6 and guests 7–10. HF/6-311+G** calculated 3D molecular electrostatic potential of the guests 7–10. The color code spans from 138 (red) to 177 kcal/mol (blue). Partial 1H NMR spectra (300 MHz, CD3CN/CDCl3 4:3

Solvent-free sonochemistry: Sonochemical organic synthesis in the absence of a liquid medium

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 1850–1856, doi:10.3762/bjoc.13.179

• its flake form and 1,2-phenylenediamine in its bead form. Clear separation of the reagents observed, with orange coated beads of 1,2-phenylenediamine residing at the bottom of the mixture. Chemical structures of the products obtained from the reaction between o-vanillin and 1,2-phenylenediamine

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• death, which might be caused by the release of active construct 6 from liposomes in cells. This study could be useful for further design and optimization of analogous systems for theranostic liposomal drug-delivery applications. Chemical structures of the basic compounds used in this study. Absorbance

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• -linker, the Friedel–Crafts cross-linking polymerization is promoted smoothly by anhydrous FeCl3 in dry 1,2-dichloroethane (DCE). The monomers were either commercially available (Sug-1) or prepared (Sug-2 and Sug-3) by benzylation of free sugars with benzyl bromide and sodium hydride. The chemical

• structures of Sug-2 and Sug-3 have been characterized by 1H NMR, 13C NMR, and MALDI–TOF MS. The chemical structure of the obtained polymers was confirmed by 13C CP/MAS NMR and Fourier transform infrared spectroscopy (FTIR) (Figure S1, Supporting Information File 1). For example, the backbone and structure

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• scale would require the involvement of engineers from various fields viz. chemical, instrumentation, mechanical and electrical. In such cases, it is desired to describe the process in terms of standard symbols (rather than combined chemical structures and diagrams which are most often used in the

A practical and efficient approach to imidazo[1,2-a]pyridine-fused isoquinolines through the post-GBB transformation strategy

• Taofeng Shao,
• Zhiming Gong,
• Tianyi Su,
• Wei Hao and
• Chao Che

Beilstein J. Org. Chem. 2017, 13, 817–824, doi:10.3762/bjoc.13.82

• ], but also allow access to diverse chemical structures [21] from readily accessible building blocks. In the past decades, considerable efforts have been made towards the development of new MCRs and their application to the diversity-oriented synthesis of biologically relevant molecules for drug

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• suitable plastic dishes (ibiTreat µ-Slides Angiogenesis, ibidi, Martinsried, Germany). Vesicles were allowed to settle down some minutes before acquisition of z-stacks with 1 µm step size. Top: Chemical structures of cholesterol and hydroxycholesterols with selected numbering for the carbon atoms. The

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• gives access to diverse chemical structures which could be considered for further studies, e.g., the biological activity of the triazole-based compounds and the use of threefold symmetrically substituted triaminoguanidines as novel hosts in supramolecular chemistry or as ligands in coordination

Secondary metabolome and its defensive role in the aeolidoidean Phyllodesmium longicirrum, (Gastropoda, Heterobranchia, Nudibranchia)

• Alexander Bogdanov,
• Cora Hertzer,
• Stefan Kehraus,
• Samuel Nietzer,
• Sven Rohde,
• Peter J. Schupp,
• Heike Wägele and
• Gabriele M. König

Beilstein J. Org. Chem. 2017, 13, 502–519, doi:10.3762/bjoc.13.50

• diterpenes of the chatancin type 16–19 [12]. Compounds 1 and 5 are new chemical structures. The same applies to the biscembranoids 14 and 15, which however show close resemblance to bisglaucumlides B and C [18], but differ in their stereochemistry from the latter. Since no studies regarding the

• -secogorgostan-11-ol. Chemical structures of the polyhydroxylated steroids 2–4 were established by comparison of the NMR and MS data obtained in our laboratory (Supporting Information File 1, Figures S6–11) with the reported values [27][28]. Compound 5 was isolated as colorless oil (1.5 mg). The specific optical

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

Posttranslational isoprenylation of tryptophan in bacteria

• Masahiro Okada,
• Tomotoshi Sugita and
• Ikuro Abe

Beilstein J. Org. Chem. 2017, 13, 338–346, doi:10.3762/bjoc.13.37

• post-translational isoprenylation of tryptophan. (A) Schematic representation of pheromone-induced conjugation tube formation for mating in Tremella mesenterica. (B) Chemical structures of tremerogens A-10 and a-13. The isoprenyl side chains are shown in red. (C) C-terminal amino acid sequences of the

• precursors of isoprenylated peptides and proteins. The CaaX motifs are shown in red. Chemical structures of (A) surfactin A and (B) poly-γ-glutamic acid. (A) Two types of posttranslational isoprenylations of ComX variants. The modified tryptophan residues are colored blue. The isoprenyl side chains are shown

• in boldface and colored blue. (B) Chemical structures of acyl homoserine lactones. The acyl side chains are shown in boldface. (A) Schematic representation of the signal transduction cascade of quorum sensing stimulated by the ComX pheromone in B. subtilis. (B) Amino acid sequences of the aspartate

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• B3LYP/6-31G (d, p) level of computations. Possible molecular packing arrangement in the self-assembled gel state of (a) TPM-G12 and (b) TPM-G5. Time-dependent UV–vis absorption profile of (a) Direct Red 80 (b) Crystal Violet aqueous dye solution (0.02 mM) by TPM-G12 gel (1% w/v in propan-1-ol). Chemical

• structures of triphenylmethyl-based organogelators. Gelation properties of TPM-G1 – TPM-G15a,b. Supporting Information Supporting Information File 58: Experimental part. Acknowledgements W.P.S gratefully acknowledges UGC, India for providing a Non-NET fellowship. This work was partially supported by the

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• stretching modes of the terminal phenylazide groups are observed at 2127 and 2092 cm−1, respectively [27]. PRX-Ph-Me (4c) exhibits negligible peaks in this region. In addition, proton nuclear magnetic resonance (1H NMR) spectra of 4a–c are well characterized by the chemical structures of the products

A new protocol for the synthesis of 4,7,12,15-tetrachloro[2.2]paracyclophane

• Donghui Pan,
• Yanbin Wang and
• Guomin Xiao

Beilstein J. Org. Chem. 2016, 12, 2443–2449, doi:10.3762/bjoc.12.237

• . calcd for C16H14N2O4 (298.30): C, 64.42; H, 4.73; N, 9.39; found: C, 64.32; H, 4.75; N, 9.45. Chemical structures of parylene N, parylene C, and parylene D. Chemical structures of [2.2]paracyclophane and 4,7,12,15-tetrachloro[2.2]paracyclophane. Synthesis of substituted (4-methylbenzyl)trimethylammonium

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

• John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442, doi:10.3762/bjoc.12.236

• partitioning to chemical structures. Two problems are addressed: (1) the determination of the total number of possible ways to construct a given ring by 2-, 3-, and 4-component couplings; and (2) the systematic enumeration of those possibilities. The results of the method are illustrated using cyclohexanone

• economy; green organic synthesis; integer partitioning; reactions; probability; retrosynthetic analysis; ring construction strategy; Introduction The ring motif is a key feature in chemical structures that has long attracted the attention of synthetic organic chemists in their quest to implement novel

High performance p-type molecular electron donors for OPV applications via alkylthiophene catenation chromophore extension

• Paul B. Geraghty,
• Calvin Lee,
• Jegadesan Subbiah,
• Wallace W. H. Wong,
• James L. Banal,
• Mohammed A. Jameel,
• Trevor A. Smith and
• David J. Jones

Beilstein J. Org. Chem. 2016, 12, 2298–2314, doi:10.3762/bjoc.12.223

• performance OPV devices and the translation to large area and printed OPV devices. Chemical structures of molecular materials with the following variations; BTxR, alkyl side chains of the terthiophene bridging arm and BXR, oligothiophene bridging arm. BQR thermal and POM properties. a) DSC thermogram of BQR

Tunable microwave-assisted method for the solvent-free and catalyst-free peracetylation of natural products

• Manuela Oliverio,
• Paola Costanzo,
• Monica Nardi,
• Carla Calandruccio,
• Raffaele Salerno and
• Antonio Procopio

Beilstein J. Org. Chem. 2016, 12, 2222–2233, doi:10.3762/bjoc.12.214

• Supporting Information File 1). Chemical structures of non-fully acetylated forms, i.e., tetra-O-acetylated-quercetin (8% of the mixture, entry B, Figure 3), di-O-acetylated quercetin (60% of the mixture, entry C, Figure 3), tri-O-acetylated quercetin (7% of the mixture, entry D, Figure 3), mono-O-acetylated

• , 155.00, 156.96, 168.07, 168.21, 168.39, 169.59, 169.93, 170.07, 170.23, 170.41. Chemical structures of bioactive substrates and their partition in subsets. MW-assisted acetylation T-program for different subset of substrates. LCHRMS (m/z, [M + Na]+ and [M − H]− only for entry F) spectrum of O-acetylated

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• evaporator. The devices were characterized using a Oriel Sol2A solar simulator and a Keithley 2400 SourceMeter. The active area of each solar cell is 0.20 cm2. a) Azadipyrromethene ligand labeling positioning; b and c) chelates; d) estimated HOMO/LUMO energy levels [9]. Chemical structures of the fluorinated

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

• Maurizio Selva,
• Alvise Perosa,
• Sandro Guidi and
• Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

• chemical structures for liquid organic salts. These properties are often referred to as “tunable catalysts”, “task-specific ionic liquids”, and “designer solvents”, which involve the concept of optimizing the use of ILs by tailoring their chemical features for a specific transformation or for classes of

Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• precursors when the overall yield of the reaction is less than 5% lower. The 1H and 13C NMR spectroscopic data for both terpyridine compounds 4 are consistent with the proposed chemical structures. Comparison with the 1H NMR spectrum of the 4′-phenyl-2,2′:6′,2″-terpyridine analogue [27][29][30] evidences

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• isotope pattern deconvolution in mass spectra of TTA-DPP4 and TTA-DPP2 showed good agreements with the theoretical isotope patterns, supporting their chemical structures. Synthesis of TTA-DPP2: This compound was prepared in a similar fashion to TTA-DPP4, using 3 (0.31 g, 0.33 mmol) and 4 (0.53 g, 0.69

• AM 1.5G solar illumination at 100 mW cm−2 (1 sun), using a Xe lamp-based Bunko-Keiki SRO-25 GD solar simulator. The light intensity was calibrated using a standard silicon photovoltaic reference cell. Chemical structures of TTA-DPP4 and TTA-DPP2. HOMO and LUMO distributions, calculated energy levels