- Synthesis of Tetradecapentaenoic Acid Derivatives
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A 12-stage method for the stereoselective synthesis of tetradecapentaenoic acid derivatives using phosphoric reagents was developed. The key step in the synthesis is the Z-selective Wittig reaction between sorbaldehyde and triphenylphosphonium (6-methoxycarbonyl)hexanilide, as well as the Ramirez-Corey-Fuchs reaction and the Trost-Kazmaier rearrangement. The synthesized (2E,4E,8Z,10E,12E)-N-isobutyltetradeca-2,4,8,10,12-pentaenamide corresponds to a natural compound called γ-Sansho?l.
- Kolodyazhnaya,Kolodyazhny
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- Solid phase synthesis of liquid crystalline oligopeptides
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Structurally well-defined liquid crystalline oligopeptides based upon a side-chain mesogenically substituted L-lysine residue are prepared via solid phase peptide synthesis (SPPS).
- Cormack, Peter A. G.,Moore, Barry D.,Sherrington, David C.
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- Supramolecular assemblies from amphiphilic homopolymers: Testing the scope
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It has been shown by us in a recent communication that homopolymers, in which each repeat unit contains a hydrophilic and a hydrophobic head group, are capable of forming environment-dependent micellar or inverse micellar assemblies. A systematic structure-property relationship study is carried out here to test the scope of the design. We show here that the molecular design is indeed broadly applicable and that there is a significant gain in the critical aggregation concentrations of these polymers, as compared to the small molecule counterparts. We also show that the design can be tuned to achieve vesicle-type assemblies, which further expands the repertoire of amphiphilic homopolymers in a variety of areas. Characterizations of these assemblies have been carried out using transmission electron microscopy, dynamic light scattering, static light scattering, and dye incorporation experiments.
- Savariar, Elamprakash N.,Aathimanikandan, Sivakumar V.,Thayumanavan
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- PREPARATION OF ANOMERIC PAIRS OF 1-THIOGLYCOSIDES: USE OF ANOMERIZATION CATALYZED BY BORON TRIFLUORIDE
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Anomeric pairs of some alkyl 1-thioaldopyranosides of D-galactose, D-glucose, D-mannose, 2-acetamido-2-deoxy-D-glucose, 2-acetamido-2-deoxy-D-galactose, and L-fucose were prepared.The per-O-acetylated, 1,2-trans anomers of 6-(trifluoroacetamido)hexyl 1-thioaldopyranosides and 5-(methoxycarbonyl)pentyl 1-thioaldopyranosides were anomerized with boron trifluoride in dichloromethane.The anomeric mixtures were then separated by chromatography, using columns of either silica gel or an ion-exchange resin.De-blocking of the separated compounds provided pure anomers of 6-aminohexyl 1-thioaldopyranosides or 5-carboxypentyl 1-thioaldopyranosides.The aglycons of the latter glycosides were further extended by reaction with aminoacetaldehyde diethyl acetal, which, after deacetalization of the products, provided an ω-aldehydo group.These series of glycosides could be readily coupled to proteins or solid matrices.
- Connolly, Daniel T.,Roseman, Saul,Lee, Yuan C.
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- Superacidic porous polymer catalyst and its application in esterification of carboxylic acid
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Two solid acid catalysts, SAC1 and SAC2, with porous structure obtained from mesoporous hard template were synthesized and characterized by Fourier transform infrared spectroscopy, acid-base titration, nitrogen adsorption/desorption, scanning electron mic
- Park, Eun Joo,Bae, Chulsung
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- RGD-conjugated two-photon absorbing near-IR emitting fluorescent probes for tumor vasculature imaging
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Observation of the activation and inhibition of angiogenesis processes is important in the progression of cancer. Application of targeting peptides, such as a small peptide that contains adjacent l-arginine (R), glycine (G) and l-aspartic acid (D) residues can afford high selectivity and deep penetration in vessel imaging. To facilitate deep tissue vasculature imaging, probes that can be excited via two-photon absorption (2PA) in the near-infrared (NIR) and subsequently emit in the NIR are essential. In this study, the enhancement of tissue image quality with RGD conjugates was investigated with new NIR-emitting pyranyl fluorophore derivatives in two-photon fluorescence microscopy. Linear and nonlinear photophysical properties of the new probes were comprehensively characterized; significantly the probes exhibited good 2PA over a broad spectral range from 700-1100 nm. Cell and tissue images were then acquired and examined, revealing deep penetration and high contrast with the new pyranyl RGD-conjugates up to 350 μm in tumor tissue.
- Yue, Xiling,Morales, Alma R.,Githaiga, Grace W.,Woodward, Adam W.,Tang, Simon,Sawada, Junko,Komatsu, Masanobu,Liu, Xuan,Belfield, Kevin D.
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- Synthesis of polysiloxane-based quaternized imidazolium salts with a hydroxy group at the end of alkyl groups
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A series of polysiloxane derivatives having quaternized imidazolium moieties with hydroxyalkyl groups ([HPImnOH]Xs) (where n is the number of methylene group and X is counter anion) were prepared by quaternization of poly(3-chloropropylmethylsiloxane) (P1) using 1-(ω-hydroxyalkyl)imidazole derivatives (ImnOHs) and anion-exchange reaction using lithium bis(trifluoromethanesulfonyl)imide. Polysiloxane-based quaternized imidazolium salts having hydroxyalkyl groups with chloride anion ([HPImnOH]Cls) were obtained with high quaternization ratio of approximately 100 mol%. The glass transition temperatures (Tgs) of [HPImnOH]Xs were reduced by introducing a hydroxy group at the end of alkyl groups; however, no significant reduction in Tgs was observed by anion exchange from chloride anion to bis(trifluoromethanesulfonyl)imide one (Tf2N-).
- Ichikawa, Tsukasa,Wako, Tsuyoshi,Nemoto, Nobukatsu
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- A modular approach toward block copolymers
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A novel methodology for the formation of block copolymers has been developed that combines ring- opening metathesis polymerization (ROMP) with functional chain-transfer agents (CTAs) and self-assembly. Telechelic homopolymers of cyclooctene derivatives en
- Higley, Mary Nell,Pollino, Joel M.,Hollembeak, Eric,Weck, Marcus
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- Polymethylene derivatives of nucleic bases with ω-functional groups: VI. [8-(2-oxocyclohexyl)-9-oxooctyl]pyrimidines as potential inhibitors of pyrimidine phosphorylases
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New polymethylene derivatives of nucleic bases with β-diketo function in ω-position were prepared by alkylation of uracil, thymine, and cytosine. Their physicochemical properties and effect on the E. coli uridine and thimidine phosphorylases were studied.
- Komissarov,Panova,Kritzyn
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- Coordination-Mediated Synthesis of Purification-Free Bivalent 99mTc-Labeled Probes for in Vivo Imaging of Saturable System
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In the synthesis of technetium-99m (99mTc) labeled target-specific ligands, the presence of a large excess of unlabeled ligands over 99mTc in the injectate hinders target accumulation of 99mTc-labeled ligands by competing for target molecules. To circumvent the problem, we recently developed a concept of the metal coordination-mediated multivalency, and proved the concept with a 99mTc-labeled trivalent compound [99mTc(CO)3(CN-RGD)3]+. In this study, D-penicillamine (Pen) was selected as a chelating molecule and a cyclic RGDfK peptide was conjugated to Pen via a hexanoic linkage (Pen-Ahx-c(RGDfK)). 99mTc complexation reaction, and the stability, integrin αvβ3 binding affinity, and biodistribution of the 99mTc-labeled probe were investigated to evaluate the applicability of the concept to bivalent probes. 99mTc-[Pen-Ahx-c(RGDfK)]2 was obtained over 95% radiochemical yields under low Pen-Ahx-c(RGDfK) concentration (50 μM). 99mTc-[Pen-Ahx-c(RGDfK)]2 showed approximately 10-times higher integrin αvβ3 binding affinity than the monovalent compounds, Pen-Ahx-c(RGDfK) and c(RGDyV). In biodistribution studies, the tumor accumulation of 99mTc-[Pen-Ahx-c(RGDfK)]2 was decreased to 77% and 43% of HPLC-purified (Pen-Ahx-c(RGDfK)-free) 99mTc-[Pen-Ahx-c(RGDfK)]2 by the presence of 5 nmol of unlabeled Pen-Ahx-c(RGDfK) and Re-[Pen-Ahx-c(RGDfK)]2, respectively. 99mTc-[Pen-Ahx-c(RGDfK)]2 provided tumor image without removing unlabeled ligand, while a 99mTc-labeled monovalent probe prepared from a monovalent ligand could not. These findings indicate the availability of the design concept to prepare 99mTc-labeled bivalent probes with a variety of 99mTc core and other metallic radionuclides of clinical relevance.
- Taira, Yuichiro,Uehara, Tomoya,Tsuchiya, Masao,Takemori, Hideaki,Mizuno, Yuki,Takahashi, Shiori,Suzuki, Hiroyuki,Hanaoka, Hirofumi,Akizawa, Hiromichi,Arano, Yasushi
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- ALKYL TELLURAALKANOATES CnH2n+1Te(CH2)mCOOR (R = CH3, C2H5 OR H)
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Methyl telluraalkanoates, CnH2n + 1Te(CH2)mCOOR (n, m: 4, 7; 6, 4; 6, 7; 6, 9; 7, 4; 8, 7; 11, 2; 11, 5; 18, 11) were synthesized in yields ranging from 33 to 82 percent based on the quantities of the methyl ω-bromoalkanoates substrates.Disodium ditelluride was obtained from tellurium and sodium in ethylenediamine and was treated with alkyl bromides to give dialkyl ditellurides.The crude ditellurides were reduced with NaBH4 to the alkane tellurolates which were coupled with methyl ω-bromoalkanoates to give the methyl telluraalkanoates.Ethyl 4-tellurapentadecanoatewas prepared similarly from ethyl 3-bromopropanoate.The telluraalkanoates were characterized by elemental analyses, mass spectrometry, NMR spectrometry, and UV and IR spectrophotometry.Telluraalkanoates radiolabeled with 123mTe or other radioisotopes have been reported elsewhere to be preferentially taken up by the heart and promise to be useful as myocardial imaging agents.
- Grigsby, Robert A.,Irgolic, Kurt J.,Knapp, Furn F.
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- AZACYANINE DYES AND USE THEREOF
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The application provides fluorescent dyes, which are cyanine dyes that incorporate additional aza moieties in the indolenium heterocycles and/or in the methine chains connecting them. Symmetrical and unsymmetrical chemically reactive azacyanine dyes are described for conjugation, as well as their bioconjugates for in-vitro and in-vivo assays and fluorescence imaging.
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(2019/10/15)
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- CONDUCTING POLYMERS AND USES THEREOF
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The present invention generally relates to the field of conducting polymers. More specifically, the present invention relates to polymerisable monomers comprising a probe capable of binding one or more nucleic acids or comprising a nucleic acid or an analogue thereof, conducting polymers comprising monomer units of such monomers, and methods of making such polymers. The present invention also relates to sensors comprising the polymers, sensor systems comprising the sensors, methods of making the sensors, and methods for determining the presence or absence or amount of targets employing the sensors. The present invention also relates to methods, systems and apparatuses for amplifying nucleic acids employing the conducting polymers.
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Page/Page column 68; 74; 75
(2018/03/28)
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- AZACYANINE DYES AND USE THEREOF
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The application provides fluorescent dyes, which are cyanine dyes that incorporate additional aza moieties in the indolenium heterocycles and/or in the methine chains connecting them. Symmetrical and unsymmetrical chemically reactive azacyanine dyes are described for conjugation, as well as their bioconjugates for in-vitro and in-vivo assays and fluorescence imaging.
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Paragraph 0428-0429
(2018/04/13)
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- Stereoselective total synthesis of Oxylipin from open chain gluco-configured building block
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Total synthesis of naturally occurring Oxylipin has been achieved from open chain gluco-configured building block which is readily assembled from inexpensive and commercially available D-(+)-gluconolactone. Grignard reaction and Wittig olefination reactions are key steps for the requisite C–C bond formation.
- Borkar, Santosh Ramdas,Aidhen, Indrapal Singh
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- Mannose-based graft polyesters with tunable binding affinity to concanavalin A
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Glycopolymers have been widely used to understand the interactions between carbohydrates and lectins, which facilitate the diagnosis and detection of disease and pathogens as well as the development of vaccines. While studies have been focused on the correlation of glycopolymer structure and their binding to lectins, graft-type glycopolyesters are uncommon. Herein, we report the design and synthesis of mannose-based graft polyesters by “grafting-from” method and investigate their interactions with Concanavalin A (Con A). As confirmed by 1H NMR spectroscopy and sulfuric acid-UV method, graft polyesters with different lengths of mannose graft were successfully synthesized. Our results from turbidimetry binding assay showed that graft polyesters with longer mannose graft exhibit higher initial binding rate (ki). Isothermal titration calorimetry measurements of these graft polyesters with Con A showed that polymers exhibit higher binding affinity (ka) with the number of side chain mannose. This study provides understanding of the interaction between Con A and mannose-based graft polyesters, which can be employed for the development of glycopolymeric therapeutics.
- Xie, Yixuan,Peng, Chao,Gao, Yunyi,Liu, Xiaohong,Liu, Tianbo,Joy, Abraham
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p. 3908 - 3917
(2017/10/07)
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- Nickel-Catalyzed Azide-Alkyne Cycloaddition to Access 1,5-Disubstituted 1,2,3-Triazoles in Air and Water
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Transition-metal-catalyzed or metal-free azide-alkyne cycloadditions are methods to access 1,4- or 1,5-disubstituted 1,2,3-triazoles. Although the copper-catalyzed cycloaddition to access 1,4-disubstituted products has been applied to biomolecular reaction systems, the azide-alkyne cycloaddition to access the complementary 1,5-regioisomers under aqueous and ambient conditions remains a challenge due to limited substrate scope or moisture-/air-sensitive catalysts. Herein, we report a method to access 1,5-disubstituted 1,2,3-triazoles using a Cp2Ni/Xantphos catalytic system. The reaction proceeds both in water and organic solvents at room temperature. This protocol is simple and scalable with a broad substrate scope including both aliphatic and aromatic substrates. Moreover, triazoles attached with carbohydrates or amino acids are prepared via this cycloaddition.
- Kim, Woo Gyum,Kang, Mi Eun,Lee, Jae Bin,Jeon, Min Ho,Lee, Sungmin,Lee, Jungha,Choi, Bongseo,Cal, Pedro M. S. D.,Kang, Sebyung,Kee, Jung-Min,Bernardes, Gon?alo J. L.,Rohde, Jan-Uwe,Choe, Wonyoung,Hong, Sung You
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supporting information
p. 12121 - 12124
(2017/09/12)
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- The scope and mechanism of palladium-catalysed Markovnikov alkoxycarbonylation of alkenes
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Hydroesterification reactions represent a fundamental type of carbonylation reaction and constitute one of the most important industrial applications of homogeneous catalysis. Over the past 70 years, numerous catalyst systems have been developed that allow for highly linear-selective (anti-Markovnikov) reactions and are used in industry to produce linear carboxylates starting from olefins. In contrast, a general catalyst system for Markovnikov-selective alkoxycarbonylation of aliphatic olefins remains unknown. In this paper, we show that a specific palladium catalyst system consisting of PdX2/N-phenylpyrrole phosphine (X, halide) catalyses the alkoxycarbonylation of various alkenes to give the branched esters in high selectivity (branched selectivity up to 91%). The observed (and unexpected) selectivity has been rationalized by density functional theory computation that includes a dispersion correction.
- Li, Haoquan,Dong, Kaiwu,Jiao, Haijun,Neumann, Helfried,Jackstell, Ralf,Beller, Matthias
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p. 1159 - 1166
(2016/11/28)
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- Differential Targeting of Human Topoisomerase II Isoforms with Small Molecules
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(Chemical Equation Presented). The TOP2 poison etoposide has been implicated in the generation of secondary malignancies during cancer treatment. Structural similarities between TOP2 isoforms challenge the rational design of isoform-specific poisons to further delineate these processes. Herein, we describe the synthesis and biological evaluation of a focused library of etoposide analogues, with the identification of two novel small molecules exhibiting TOP2B-dependent toxicity. Our findings pave the way toward studying isoform-specific cellular processes by means of small molecule intervention.
- Mariani, Angelica,Bartoli, Alexandra,Atwal, Mandeep,Lee, Ka C.,Austin, Caroline A.,Rodriguez, Rapha?l
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supporting information
p. 4851 - 4856
(2015/06/25)
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- Site-selective aliphatic C-H bromination using N -bromoamides and visible light
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Transformations that selectively functionalize aliphatic C-H bonds hold significant promise to streamline complex molecule synthesis. Despite the potential for site-selective C-H functionalization, few intermolecular processes of preparative value exist. Herein, we report an approach to unactivated, aliphatic C-H bromination using readily available N-bromoamide reagents and visible light. These halogenations proceed in useful chemical yields, with substrate as the limiting reagent. The site selectivities of these radical-mediated C-H functionalizations are comparable (or superior) to the most selective intermolecular C-H functionalizations known. With the broad utility of alkyl bromides as synthetic intermediates, this convenient approach will find general use in chemical synthesis.
- Schmidt, Valerie A.,Quinn, Ryan K.,Brusoe, Andrew T.,Alexanian, Erik J.
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supporting information
p. 14389 - 14392
(2014/12/10)
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- PRECURSOR USED FOR LABELING HEPATORCYTE RECEPTOR AND CONTAINING TRISACCHARIDE AND DIAMIDE DEMERCAPTIDE LIGAND, METHOD FOR PREPARING THE SAME, RADIOTRACER AND PHARMACEUTICAL COMPOSITION OF THE SAME
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A precursor used for labeling hepatocyte receptors and applied to radiotracers for imaging or pharmaceutical compositions for liver cancers is revealed. The precursor is a bifunctional compound. The bifunctional group includes a trisaccharide structure an
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Paragraph 0064; 0065; 0066; 0067
(2014/02/16)
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- Synthesis and evaluation of radioiodinated acyloxymethyl ketones as activity-based probes for cathepsin B
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Dipeptidyl (acyloxy)methyl ketones (AOMKs) were functionalized with different iodine-containing prosthetic groups to generate a library of candidate cathepsin B probes. Compound 23a, (S)-20-[(S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanamido]-1-(4-iod
- Edem, Patricia E.,Czorny, Shannon,Valliant, John F.
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supporting information
p. 9564 - 9577
(2015/02/02)
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- Thermodynamic stability and relaxation studies of small, triaza-macrocyclic Mn(ii) chelates
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Due to its favorable relaxometric properties, Mn2+ is an appealing metal ion for magnetic resonance imaging (MRI) contrast agents. This paper reports the synthesis and characterization of three new triazadicarboxylate-type ligands and their Mn
- De Sá, Arsénio,Bonnet, Célia S.,Geraldes, Carlos F. G. C.,Tóth, éva,Ferreira, Paula M. T.,André, Jo?o P.
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p. 4522 - 4532
(2013/05/09)
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- Investigation of the origin and synthetic application of the pseudodilution effect for Pd-catalyzed macrocyclisations in concentrated solutions with immobilized catalysts
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Immobilized Pd-complexes allowed macrocyclisations via the Tsuji-Trost-reaction in concentrated solutions. Systematic studies suggest that the origin of this pseudodilution effect is neither film diffusion nor gel diffusion, but the reduction in conformational freedom of intermediates and intramolecular prenucleophile activation. In contrast a pseudodilution effect could not be observed for Sonogashira- and Suzuki-macrocyclisations.
- Brehm, Elisabeth,Breinbauer, Rolf
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supporting information
p. 4750 - 4756
(2013/07/26)
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- The discovery and optimization of novel dual inhibitors of topoisomerase ii and histone deacetylase
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A novel class of podophyllotoxin derivatives have been designed and synthesized based on the synergistic antitumor effects of topoisomerase II and histone deacetylase inhibitors. Their inhibitory activities towards histone deacetylases and Topo II and their cytotoxicities in cancer cell lines were evaluated. The aromatic capping group connection, linker length and zinc-binding group were systematically varied and preliminary conclusions regarding structure-activity relationships are discussed. Among all of the synthesized hybrid compounds, compound 24d showed the most potent HDAC inhibitory activity at a low nanomolar level and exhibited powerful antiproliferative activity towards HCT116 colon carcinoma cells at a low micromolar level. Further exploration of this series led to the discovery of potent dual inhibitor 32, which exhibited the strongest in vitro cytotoxic activity.
- Zhang, Xuan,Bao, Bin,Yu, Xiuhua,Tong, Linjiang,Luo, Yu,Huang, Qingqing,Su, Mingbo,Sheng, Li,Li, Jia,Zhu, Hong,Yang, Bo,Zhang, Xiongwen,Chen, Yi,Lu, Wei
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p. 6981 - 6995
(2013/11/06)
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- Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds
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The enantioselective synthesis of novel C-linked spiroacetal-triazoles 10 is reported. The key step involves reaction of acetylenic spiroacetal 11 with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold 11 was prepared from silyl-protected Weinreb amide 19 using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.
- Kueh, Jui Thiang Brian,Choi, Ka Wai,Brimble, Margaret A.
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supporting information; experimental part
p. 5993 - 6002
(2012/08/27)
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- RADIOACTIVELY LABELED SUBSTANCE
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Provided are: a radiolabeled drug, which is efficiently accumulated in a target and has high in vivo stability; and diagnosis and treatment each using the radiolabeled drug. Specifically provided are: a radiolabeled drug showing increased accumulation in a target site, which comprises a complex composed of a ligand that is bound to a compound capable of binding to a target molecule and forms a polycoordinated complex with a metal (e.g., technetium or rhenium) and a radionuclide of the metal; the radiolabeled drug for diagnosis or treatment; a ligand for preparing the radiolabeled drug; a kit that comprises a drug comprising the ligand and a drug comprising a radionuclide of a metal, as separate package units; and a method of increasing accumulation of a radiolabeled drug in a target site, comprising using the above-mentioned radiolabeled drug.
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- Radioactively Labeled Substance
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Provided are: a radiolabeled drug, which is efficiently accumulated in a target and has high in vivo stability; and diagnosis and treatment each using the radiolabeled drug. Specifically provided are: a radiolabeled drug showing increased accumulation in a target site, which comprises a complex composed of a ligand that is bound to a compound capable of binding to a target molecule and forms a polycoordinated complex with a metal (e.g., technetium or rhenium) and a radionuclide of the metal; the radiolabeled drug for diagnosis or treatment; a ligand for preparing the radiolabeled drug; a kit that comprises a drug comprising the ligand and a drug comprising a radionuclide of a metal, as separate package units; and a method of increasing accumulation of a radiolabeled drug in a target site, comprising using the above-mentioned radiolabeled drug.
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- Antimalarial histone deacetylase inhibitors containing cinnamate or NSAID components
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Malaria is the most lethal parasite-mediated tropical infectious disease, killing 1-2 million people each year. An emerging drug target is the enzyme Plasmodium falciparum histone deacetylase 1 (PfHDAC1). We report 26 compounds designed to bind the zinc and exterior surface around the entrance to the active site of PfHDAC1, 16 displaying potent in vitro antimalarial activity (IC 50 10-fold more cytotoxic towards P. falciparum than a normal human cell type (NFF). Twenty-two inhibitors feature cinnamic acid derivatives or non-steroidal anti-inflammatory drugs (NSAIDs) as HDAC-binding components. A homology model of PfHDAC1 enzyme gives new insights to interactions likely made by some of these inhibitors. Results support PfHDAC1 as a promising new antimalarial drug target.
- Wheatley, Nicole C.,Andrews, Katherine T.,Tran, Truc L.,Lucke, Andrew J.,Reid, Robert C.,Fairlie, David P.
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supporting information; experimental part
p. 7080 - 7084
(2010/12/25)
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- Heterogeneous asymmetric Henry reaction using a chiral bis(oxazoline)-copper complex immobilized on magnetically separable mesocellular mesoporous silica support
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A chiral bis(oxazoline) ligand was immobilized onto a magnetically separable hierarchically-ordered mesocellular mesoporous silica (M-HMMS) and this new catalytic system was examined in the asymmetric Henry reaction between various aldehydes and nitrometh
- Lee, Jun-Mun,Kim, Jaeyun,Shin, Yongje,Yeom, Chang-Eun,Lee, Ji Eun,Hyeon, Taeghwan,Moon Kim
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experimental part
p. 285 - 291
(2010/05/18)
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- SUBSTITUTED ETHANOLAMINES
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The present invention relates to new substituted ethanolamine adrenergic receptor modulators, pharmaceutical compositions thereof, and methods of use thereof.
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Page/Page column 28
(2010/02/17)
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- Inhibitors selective for HDAC6 in enzymes and cells
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Histone deacetylase inhibitors with anticancer or anti-inflammatory activity bind to Class I or Class I and II HDAC enzymes. Here we compare selectivity of inhibitors of a Class II HDAC enzyme (HDAC6) and find one that retains high selectivity in macrophages.
- Gupta, Praveer K.,Reid, Robert C.,Liu, Ligong,Lucke, Andrew J.,Broomfield, Steve A.,Andrews, Melanie R.,Sweet, Matthew J.,Fairlie, David P.
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supporting information; experimental part
p. 7067 - 7070
(2011/01/03)
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- "Singapore green": A new fluorescent dye for microarray and bioimaging applications
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(Figure Presented) We have synthesized Singapore Green (SG), a structural hybrid of Tokyo Green and Rhodamine 110. This new dye is a green light-emitting substitute for 7-aminocoumarin, a blue fluorescent dye widely used in enzymatic assays. SG-conjugated
- Li, Junqi,Yao, Shao Q.
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supporting information; experimental part
p. 405 - 408
(2009/07/11)
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- High-throughput synthesis of azide libraries suitable for direct "click" chemistry and in situ screening
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A key challenge in current drug discovery is the development of high-throughput (HT) amenable chemical reactions that allow rapid synthesis of diverse chemical libraries of enzyme inhibitors. The Cu(I)-catalyzed, 1,3-dipolar cycloaddition between an azide and an alkyne, better known as "click chemistry", is one such method that has received the most attention in recent years. Despite its popularity, there is still a lack of robust and efficient chemical strategies that give access to diverse libraries of azide-containing building blocks (key components in click chemistry). We report herein a highly robust and efficient strategy for high-throughput synthesis of a 325-member azide library. The method is highlighted by its simplicity and product purity. The utility of the library is demonstrated with the subsequent "click" synthesis of the corresponding bidentate inhibitors against PTP1B.
- Srinivasan, Rajavel,Tan, Lay Pheng,Wu, Hao,Yang, Peng-Yu,Kalesh, Karunakaran A.,Yao, Shao Q.
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supporting information; experimental part
p. 1821 - 1828
(2009/06/28)
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- Polarity of the acid chain of esters and transesterification activity of acid catalysts
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The effect of polarity of the esters on the transesterification reaction rate has been investigated. The effect was studied in homogeneous and heterogeneous catalysts. The polarity of different ethyl alkanoate esters was varied by (i) increasing the number of carbon atoms in the acid alkyl chain of the esters and (ii) introducing Br and hydroxy substituents at the end of the acid chain of ethyl hexanoate. Polarity was determined through the λmax of the UV-Vis spectrum of the betaine dye dissolved in the investigated esters (ET(30) scale). The transesterification reaction was carried out with methanol and by using sulfuric acid and a Dowex DR2030 sulfonic resin as homogeneous and heterogeneous catalysts, respectively. It was observed that, in addition to steric hindrance, the polarity of the ester chain has an effect on the reaction rate of the heterogeneous acid catalysts. It is proposed that the positive or negative effect of the polarity is due to repulsive or attractive interactions of the ester chain with the polar groups of the resin and/or with the methanol molecules present in the pores. A very positive effect is found in heterogeneous acid catalysis if H-bonds can stabilize the active intermediate participating in the rate determining step. The attractive or repulsive interactions are absent in the homogeneous case.
- Alonso, D. Martin,Granados, M. Lopez,Mariscal,Douhal
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scheme or table
p. 18 - 26
(2009/06/17)
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- Primary alkyl bromides from dimethylthiocarbamates
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The conversion of primary alkyl dimethylthiocarbamates into alkyl bromides using the Vilsmeier reagent occurs in high yields in the presence of other non-acid sensitive and non-nucleophilic functional groups. Georg Thieme Verlag Stuttgart · New York.
- Moynihan, Meghan F.,Tucker, Joseph W.,Abelt, Christopher J.
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experimental part
p. 3565 - 3568
(2009/06/18)
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- BENZODIAZEPINE AND BENZOPIPERAZINE ANALOG INHIBITORS OF HISTONE DEACETYLASE
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This invention relates to compounds for the inhibition of histone deacetylase More particularly, the invention provides for compounds of formula (I): wherein A, B, D, E, X1, X2, X3, X4 and n are as defined in the specification A method of inhibiting histone deacetylase in a cell, the method comprising contacting the cell with a compound of formula (I), in an amount sufficient to inhibit histone deacetylase, is also disclosed.
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Page/Page column 81-82
(2010/11/26)
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- Invertible amphiphilic polymers
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Amphiphilic monomeric compounds and corresponding homopolymers and copolymers capable of assembly and invertible configuration in introduction to and change in fluid medium.
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Page/Page column 22
(2010/11/29)
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- A new method for constructing quaternary carbon centres: Tandem rhodium-catalysed 1,4-addition/intramolecular cyclisation
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The efficient tandem rhodium-catalysed 1,4-addition/cyclisation of 1,1′-alkenes using arylzinc chlorides is described. The simple one-step synthesis of substituted cyclopentanone and cyclohexanone derivatives is performed from acyclic precursors using relatively low catalyst loadings under mild conditions. A new quaternary carbon centre is created during the cyclisation step.
- Le Notre, Jerome,Van Mele, David,Frost, Christopher G.
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p. 432 - 440
(2008/02/07)
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- Solventless lactam synthesis by intramolecular cyclizations of α-iminoester derivatives under microwave irradiation
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We have previously reported a new synthesis of amides from esters and amines under microwave irradiation, offering much higher yields than those achieved with conventional heating [1]. We have now extended these studies to the ring closure of neat iminoes
- Zradni, Fatima-Zohra,Hamelin, Jack,Derdour, Aicha
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p. 439 - 454
(2007/10/03)
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- HISTONE DEACETYLASE INHIBITORS
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The present invention provides histone deacetylase inhibitors of general formula (I), process for the preparation of such compounds and uses of the compounds in medicine.
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- A comparison of phosphonothioic acids with phosphonic acids as phosphatase inhibitors
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Phosphorothioates, analogues of phosphate esters in which a sulfur replaces an oxygen atom in the phosphoryl group, are competent surrogate substrates for a number of phosphatases. In some cases the thio analogues show similar binding (as estimated by Ks
- Swierczek, Krzysztof,Pandey, Arti S.,Peters, John W.,Hengge, Alvan C.
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p. 3703 - 3708
(2007/10/03)
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- Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones
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Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride - alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one.
- Wolfe, Saul,Wilson, Marie-Claire,Cheng, Ming-Huei,Shustov, Gennady V.,Akuche, Christiana I.
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p. 937 - 960
(2007/10/03)
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- New 4-arylpiperidine derivatives for the treatment of pruritus
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There is provided a compound of formula I, wherein Het1, R1, R2, R3, X and n have meanings given in the description, which are useful in the prophylaxis and in the treatment of diseases mediated by opiate receptors, such as pruritus.
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- THREE-STEP PRETARGETING METHODS AND COMPOUNDS
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Methods, compounds, compositions and kits that relate to pretargeted delivery of diagnostic and therapeutic agents are disclosed. In particular, three-step pretargeting methods are described.
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- Esterification of carboxylic acids with boron trichloride
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Treatment of carboxylic acids with boron trichloride followed by addition of alcohol provides the carboxylic ester. This esterification, following BCl3 ether or ester O-C cleavage reaction conditions, proceeds cleanly in good yields with most substrates. Cleavage of benzyl esters with boron trichloride then treating with methanol affords the methyl ester.
- Dyke, Christopher A.,Bryson, Thomas A.
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p. 3959 - 3961
(2007/10/03)
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- 4-arylpiperidine derivatives for the treatment of pruritus
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There is provided a compound of formula I, wherein Het1, R1, R2, R3, X and n have meanings given in the description, which are useful in the prophylaxis and in the treatment of diseases mediated by opiate receptors, such as pruritus.
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- Cluster clearing agents
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Cluster clearing agents (CCAs) and the use thereof are discussed. CCAs are composed of a hepatic clearance directing moiety which directs the biodistribution of a CCA-containing construct to hepatic clearance; and a binding moiety which mediates binding of the CCA to a compound for which rapid hepatic clearance is desired.
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- Luminescent cyclometallated Ir(III) complexes of conjugatable carboxy-functionalized ligandsf
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Novel bifunctional ligands based on a 6′-phenyl-2,2′-bipyridine moiety are synthesised and used to prepare iridium(m) complexes [Ir(ppy)2(L)]+ (ppy = 2-phenylpyridlne anion; L = 1,2, and 4) which have the potential to serve as lumine
- Neve, Francesco,Crispini, Alessandra,Loiseau, Frederique,Campagna, Sebastiane
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p. 1399 - 1401
(2007/10/03)
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- Small molecular weight ligand-hexose containing clearing agents
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Small molecule weight clearing agents containing ligands such as biotin or biotin analogs and hexose residue, in particular galactose or N-acetyl galactosamine residues are taught. These clearing agents effectively clear anti-ligand containing conjugates
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- Hepatic-directed compounds and reagents for preparation thereof
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Hepatic-directed compounds, reagents useful in making such compounds and associated methods and compositions are discussed. Hepatic-directed compounds are processed by metabolic mechanisms, which generally differ in degree or in kind from the metabolic mechanisms encountered by compounds which are not so directed. Reagents useful in the preparation of hepatic-directed compounds include a hexose cluster characterized by multiple hexose residues connected in an iteratively branched configuration. In one embodiment, the hexose cluster comprises at least four hexose residues with each branch of the configuration having two prongs. In another embodiment, the hexose cluster comprises at least nine hexose residues with each branch of the configuration having three prongs.
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- Radiolabeled annexin conjugates with hexose and a chelator
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Radiolabeled annexin and modified annexin conjugates useful for imaging vascular thrombi are described. Methods for making and using such radiolabeled annexin conjugates are also provided.
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- Monodisperse liquid crystalline peptides
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Solid phase peptide synthesis (SPPS) has been used as a synthetic tool to prepare monodisperse mesogen-oligopeptide conjugates with novel molecular architectures. Building upon previous success in this area, we have extended our methodologies to include a mesogenically substituted L-glutamic acid residue, and incorporated this derivative, as well as the L-lysine derivative previously reported, into a variety of new structures. Some novel liquid crystalline materials have been discovered. Both α-helical and β-sheet secondary structures have been explored as alternative scaffolds for the pendant mesogenic groups. The helical systems show most promise in terms of their ease of synthesis and handling, but at the relatively lower levels of mesogenic substitution studied so far, compared to the previously reported homo-oligopeptide materials, mesophases are not observed. The β-sheet materials prepared are rather insoluble and too high melting to have any practical value as thermotropic materials without further manipulation of their structures.
- Cormack, Peter A. G.,Moore, Barry D.,Sherrington, David C.
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p. 1977 - 1983
(2007/10/03)
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