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Search for "small molecule" in Full Text gives 212 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Molecular recognition of AT-DNA sequences by the induced CD pattern of dibenzotetraaza[14]annulene (DBTAA)–adenine derivatives

  • Marijana Radić Stojković,
  • Marko Škugor,
  • Łukasz Dudek,
  • Jarosław Grolik,
  • Julita Eilmes and
  • Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2175–2185, doi:10.3762/bjoc.10.225

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  • recognition; circular dichroism; DBTAA-adenine conjugate; ds-DNA/RNA; minor groove binding; nucleic acids; Introduction The majority of natural and artificial applications involving small molecule-DNA/RNA recognition depend on several non-covalent binding modes. Typical examples are double-stranded (ds) DNA
  • /RNA sites [2][3], frequently relying upon new knowledge gained from supramolecular chemistry [4]. Among the large number of DNA/RNA sequences of biochemical interest, long homogeneous AT tracts have attracted significant attention as small molecule targets. An illustrative natural example can be found
  • advantage of nucleobase incorporation in small molecule structures for the recognition of complementary nucleotides/polynucleotides [8][9][10]. Recent studies of the novel DBTAA-adenine conjugates AP3 and AP6 (Scheme 1) showed a highly selective binding of only AP3 to poly dT among all other ss-DNA/RNA, as
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Published 12 Sep 2014

Chiral phosphines in nucleophilic organocatalysis

  • Yumei Xiao,
  • Zhanhu Sun,
  • Hongchao Guo and
  • Ohyun Kwon

Beilstein J. Org. Chem. 2014, 10, 2089–2121, doi:10.3762/bjoc.10.218

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  • have excellent catalytic activities and enantioselectivities, only a few acyclic phosphines were effective. In this context, inspired by polyfunctional chiral small-molecule catalysts, particularly amino acid and thiourea-based systems [31][32], multifunctional chiral phosphines were constructed by
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Published 04 Sep 2014

Organophosphorus chemistry

  • Paul R. Hanson

Beilstein J. Org. Chem. 2014, 10, 2087–2088, doi:10.3762/bjoc.10.217

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  • number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small
  • molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new
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Editorial
Published 04 Sep 2014

Supercritical carbon dioxide: a solvent like no other

  • Jocelyn Peach and
  • Julian Eastoe

Beilstein J. Org. Chem. 2014, 10, 1878–1895, doi:10.3762/bjoc.10.196

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  • small molecule surfactants have reapplied during the design of CO2-philic polymers. The structures of polymers discussed in this review can be seen in Table 2. Fluorinated polymers: One of the first polymers reported to be solubilised in CO2 was Krytox 16350 (Table 2, compound 16), a perfluoropolyether
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Published 14 Aug 2014

Multicomponent reactions in nucleoside chemistry

  • Mariola Koszytkowska-Stawińska and
  • Włodzimierz Buchowicz

Beilstein J. Org. Chem. 2014, 10, 1706–1732, doi:10.3762/bjoc.10.179

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  • ) represent an excellent tool for the generation of libraries of small-molecule compounds, for instance they are indispensable for the structure–activity relationship (SAR) studies. Many excellent comprehensive reviews on MCRs have been published. The reviews have covered the significant topics in this field
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Published 29 Jul 2014

Aryl substitution of pentacenes

  • Andreas R. Waterloo,
  • Anna-Chiara Sale,
  • Dan Lehnherr,
  • Frank Hampel and
  • Rik R. Tykwinski

Beilstein J. Org. Chem. 2014, 10, 1692–1705, doi:10.3762/bjoc.10.178

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  • ], and specifically 6,13-(triisopropylsilylethynyl)pentacene (TIPSPc) [13][14]. The latter was synthesized by Anthony over a decade ago [16], but it is still a leading focus of the scientific community. Substituted pentacenes can offer several advantages to other small molecule semiconductors, including
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Published 28 Jul 2014

An experimental and theoretical NMR study of NH-benzimidazoles in solution and in the solid state: proton transfer and tautomerism

  • Carla I. Nieto,
  • Pilar Cabildo,
  • M. Ángeles García,
  • Rosa M. Claramunt,
  • Ibon Alkorta and
  • José Elguero

Beilstein J. Org. Chem. 2014, 10, 1620–1629, doi:10.3762/bjoc.10.168

Graphical Abstract
  • heterocycles it can be said that they have relevant biological and medicinal chemistry properties, because, for instance, over 80% of top small molecule drugs by US retail sales in 2010 contain at least one heterocyclic fragment in their structures [1]. Benzimidazoles besides being the skeleton of many
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Published 16 Jul 2014

Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester

  • Antal Harsanyi,
  • Graham Sandford,
  • Dmitri S. Yufit and
  • Judith A.K. Howard

Beilstein J. Org. Chem. 2014, 10, 1213–1219, doi:10.3762/bjoc.10.119

Graphical Abstract
  • –fluorine bonds are ‘man-made’. Syntheses rely either on the construction of carbon–fluorine bonds using a fluorinating agent (‘late-stage’ fluorination) or the application of polyfunctional fluorine-containing small molecule building blocks (‘early stage’ fluorination) which may be employed in further
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Published 22 May 2014

Automated solid-phase peptide synthesis to obtain therapeutic peptides

  • Veronika Mäde,
  • Sylvia Els-Heindl and
  • Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

Graphical Abstract
  • interesting target on the pharmaceutical market. In terms of molecular weight, peptides bridge the gap between small molecule drugs (<500 Da) and protein-based pharmaceuticals (>5,000 Da) and enable a possible medication of incurable pathologies [3]. Diseases such as cancer, diabetes, obesity but also
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Published 22 May 2014

Rapid pseudo five-component synthesis of intensively blue luminescent 2,5-di(hetero)arylfurans via a Sonogashira–Glaser cyclization sequence

  • Fabian Klukas,
  • Alexander Grunwald,
  • Franziska Menschel and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2014, 10, 672–679, doi:10.3762/bjoc.10.60

Graphical Abstract
  • structurally related to small molecule inhibitors of p53-HDM-2 [21][22][23]. Electronic properties and computational studies All title compounds 2 display strong fluorescence in solution and in the solid state upon UV excitation (Figure 1). Therefore, the absorption and emission spectra of all compounds 2 were
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Published 18 Mar 2014

Integration of enabling methods for the automated flow preparation of piperazine-2-carboxamide

  • Richard J. Ingham,
  • Claudio Battilocchio,
  • Joel M. Hawkins and
  • Steven V. Ley

Beilstein J. Org. Chem. 2014, 10, 641–652, doi:10.3762/bjoc.10.56

Graphical Abstract
  • pyrazine 2 to piperazine 1 (Figure 2b). Both of these steps involve flowing through heterogeneous catalysts, a metal oxide for the hydration of the nitrile and a supported precious metal for the hydrogenation of the heteroaromatic ring. Furthermore, both steps involve the addition of a volatile small
  • molecule to the substrate with no byproducts: the addition of water for the nitrile hydration, and the addition of hydrogen to the heteroarene for the reduction. Thus, this sequence is ideal for a fully continuous multi-step process. Results and Discussion Nitrile hydration Primary amides can be prepared
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Published 12 Mar 2014

The Flögel-three-component reaction with dicarboxylic acids – an approach to bis(β-alkoxy-β-ketoenamides) for the synthesis of complex pyridine and pyrimidine derivatives

  • Mrinal K. Bera,
  • Moisés Domínguez,
  • Paul Hommes and
  • Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2014, 10, 394–404, doi:10.3762/bjoc.10.37

Graphical Abstract
  • powerful tools for the assembly of small-molecule libraries [1][2]. MCRs leading to functionalized N-heterocycles [3][4][5][6][7] have long been known before the general concept of MCRs was introduced, e.g. the Hantzsch dihydropyridine synthesis [8] or the Biginelli reaction [9] leading to
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Published 13 Feb 2014

Physalin H from Solanum nigrum as an Hh signaling inhibitor blocks GLI1–DNA-complex formation

  • Midori A. Arai,
  • Kyoko Uchida,
  • Samir K. Sadhu,
  • Firoj Ahmed and
  • Masami Ishibashi

Beilstein J. Org. Chem. 2014, 10, 134–140, doi:10.3762/bjoc.10.10

Graphical Abstract
  • ) Disruption of the GLI1–DNA complex in the final stage of this signaling pathway is one of the most attractive molecular mechanisms of Hh inhibitors. Recently, we reported the first small molecule, which directly inhibits the GLI1–DNA complex formation [22].GANT61, a synthetic compound, has been reported to
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Published 13 Jan 2014

Modulating NHC catalysis with fluorine

  • Yannick P. Rey and
  • Ryan Gilmour

Beilstein J. Org. Chem. 2013, 9, 2812–2820, doi:10.3762/bjoc.9.316

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  • , Münster, Germany 10.3762/bjoc.9.316 Abstract Fluorination often confers a range of advantages in modulating the conformation and reactivity of small molecule organocatalysts. By strategically introducing fluorine substituents, as part of a β-fluoroamine motif, in a triazolium pre-catalyst, it was
  • :13.0). Keywords: catalysis; enantioselectivity; fluorine; gauche effect; organo-fluorine; Steglich rearrangement; Introduction Molecular editing using fluorine is a powerful strategy to modulate the conformation and reactivity of small molecule organocatalysts [1][2][3]. The negligible steric penalty
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Published 06 Dec 2013

The regulation and biosynthesis of antimycins

  • Ryan F. Seipke and
  • Matthew I. Hutchings

Beilstein J. Org. Chem. 2013, 9, 2556–2563, doi:10.3762/bjoc.9.290

Graphical Abstract
  • chemotherapeutic agents whose mode of action is to trigger apoptosis. A small molecule screen identified antimycins as potent inhibitors of Bcl-2-related proteins where they were shown to bind to the hydrophobic groove [28]. A synthetic derivative of antimycin A3, 2-methoxyantimycin A3 (Figure 1), no longer
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Published 19 Nov 2013

Triol-promoted activation of C–F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane

  • Pier Alexandre Champagne,
  • Alexandre Saint-Martin,
  • Mélina Drouin and
  • Jean-François Paquin

Beilstein J. Org. Chem. 2013, 9, 2451–2456, doi:10.3762/bjoc.9.283

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  • agent, which means we could potentially use the triol as an additive rather than a solvent. Altogether, this strategy would represent a unique metal-free and unprecedented small-molecule-mediated activation of C–F bonds. Herein, we report the feasibility of this concept for the amination of benzylic
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Published 13 Nov 2013

Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

  • Olivia N. Monaco,
  • Sarah C. Tomas,
  • Meghan K. Kirrane and
  • Amy M. Balija

Beilstein J. Org. Chem. 2013, 9, 2320–2327, doi:10.3762/bjoc.9.266

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  • hybrid dendrimers could be isolated and used in different solvent environments without being degraded. Due to their hydrophobic periphery and larger size, hybrid dendrimers 11–13 were envisioned as potential scaffolds to encapsulate small molecule organic pollutants such as polycyclic aromatic
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Published 31 Oct 2013

Activation of cryptic metabolite production through gene disruption: Dimethyl furan-2,4-dicarboxylate produced by Streptomyces sahachiroi

  • Dinesh Simkhada,
  • Huitu Zhang,
  • Shogo Mori,
  • Howard Williams and
  • Coran M. H. Watanabe

Beilstein J. Org. Chem. 2013, 9, 1768–1773, doi:10.3762/bjoc.9.205

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  • Dinesh Simkhada Huitu Zhang Shogo Mori Howard Williams Coran M. H. Watanabe Texas A&M University, Department of Chemistry, College Station, TX 77843, USA 10.3762/bjoc.9.205 Abstract At least 65% of all small molecule drugs on the market today are natural products, however, re-isolation of
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Published 29 Aug 2013

Computational study of the rate constants and free energies of intramolecular radical addition to substituted anilines

  • Andreas Gansäuer,
  • Meriam Seddiqzai,
  • Tobias Dahmen,
  • Rebecca Sure and
  • Stefan Grimme

Beilstein J. Org. Chem. 2013, 9, 1620–1629, doi:10.3762/bjoc.9.185

Graphical Abstract
  • from the experimental value by only 0.5 kcal mol−1. This deviation (about 5%) is within the typical error limits of DFT-D3 and the experimental methods. In passing it is noted that the D3-dispersion correction to the barrier even for this relatively small molecule is substantial (decrease by 0.7 kcal
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Published 08 Aug 2013

ML212: A small-molecule probe for investigating fluconazole resistance mechanisms in Candida albicans

  • Willmen Youngsaye,
  • Cathy L. Hartland,
  • Barbara J. Morgan,
  • Amal Ting,
  • Partha P. Nag,
  • Benjamin Vincent,
  • Carrie A. Mosher,
  • Joshua A. Bittker,
  • Sivaraman Dandapani,
  • Michelle Palmer,
  • Luke Whitesell,
  • Susan Lindquist,
  • Stuart L. Schreiber and
  • Benito Munoz

Beilstein J. Org. Chem. 2013, 9, 1501–1507, doi:10.3762/bjoc.9.171

Graphical Abstract
  • were eliminated. Results and Discussion Screening results In order to identify nonfungitoxic chemosensitizers of Candida albicans, compounds from the NIH’s Molecular Libraries Small Molecule Repository (MLSMR) [17] were evaluated in the screening cascade summarized in Figure 1. The C. albicans strains
  • fluconazole-resistant Candida albicans clinical isolates. Among the numerous hits, 3-phenylindazole 1 was selected for chemical optimization, resulting in the identification of 3-(3-anisoyl)indazole 36 as new small-molecule probe (ML212) to facilitate investigation of the various mechanisms used by C
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Published 26 Jul 2013

Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation

  • Lynnie Trzoss,
  • Jing Xu,
  • Michelle H. Lacoske and
  • Emmanuel A. Theodorakis

Beilstein J. Org. Chem. 2013, 9, 1135–1140, doi:10.3762/bjoc.9.126

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  • . Keywords: natural products; neurodegenerative diseases; neurotrophic small molecule; organocatalysis; total synthesis; Introduction Neurotrophins are a family of endogenous proteins that are vital for neuron function, survival, and regeneration [1][2][3]. As such, they have prompted intense studies toward
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Published 12 Jun 2013

Enhancement of efficiency in organic photovoltaic devices containing self-complementary hydrogen-bonding domains

  • Rohan J. Kumar,
  • Jegadesan Subbiah and
  • Andrew B. Holmes

Beilstein J. Org. Chem. 2013, 9, 1102–1110, doi:10.3762/bjoc.9.122

Graphical Abstract
  • -processing, leading to cost and energy input advantages in device manufacture. Recently, a donor–acceptor small molecule with a cyanopyridone moiety as the acceptor motif and displaying moderate photovoltaic efficiency in a BHJ device with a fullerene was reported [20]. The efficiency of these optimized
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Published 06 Jun 2013

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

  • Jiayang Li,
  • Yi Kuang,
  • Junfeng Shi,
  • Yuan Gao,
  • Jie Zhou and
  • Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

Graphical Abstract
  • of small molecule hydrogels formed by NSAID derivatives [48][54][55][56] we intend to explore supramolecular hydrogels of other NSAIDs. Specifically, we use naproxen (denoted as Npx in this report), an over-the-counter NSAID, to generate a new hydrogelator 1a that only consists of naproxen and
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Published 10 May 2013

Synthesis and physicochemical characterization of novel phenotypic probes targeting the nuclear factor-kappa B signaling pathway

  • Paul M. Hershberger,
  • Satyamaheshwar Peddibhotla,
  • E. Hampton Sessions,
  • Daniela B. Divlianska,
  • Ricardo G. Correa,
  • Anthony B. Pinkerton,
  • John C. Reed and
  • Gregory P. Roth

Beilstein J. Org. Chem. 2013, 9, 900–907, doi:10.3762/bjoc.9.103

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  • diseases and has recently been implicated in the onset of cancer. This report provides a synthetic and compound-based property summary of five pathway-related small-molecule chemical probes identified and optimized within the National Institutes of Health-Molecular Libraries Probe Center Network (NIH-MLPCN
  • the small-molecule compounds discovered within the HTS process. The program then advanced a broader probe-production initiative (MLPCN) in 2008. This consortium resulted in the harnessing of chemical biology resources from four comprehensive centers and five specialty centers, which focused on either
  • with advancing basic in vitro and in vivo studies for testing new hypotheses in disease modulation. Within this report, the outcomes of two Sanford-Burnham projects for chemical probe discovery are discussed, highlighting five examples of thematic small-molecule chemical probes discovered through our
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Published 08 May 2013

Synthesis of skeletally diverse alkaloid-like molecules: exploitation of metathesis substrates assembled from triplets of building blocks

  • Sushil K. Maurya,
  • Mark Dow,
  • Stuart Warriner and
  • Adam Nelson

Beilstein J. Org. Chem. 2013, 9, 775–785, doi:10.3762/bjoc.9.88

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  • half of all known organic compounds are based on only 0.25% of the known molecular scaffolds [9]! This uneven coverage of chemical space is also typical of small-molecule screening collections [7][10]. Consequently, the biological relevance of most known scaffolds has been poorly explored. The field of
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Published 22 Apr 2013
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