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T : 목차정보

Tetrahedron 18건

  1. [해외논문]   Fluorinated piperidine iminosugars and their N-alkylated derivatives: Synthesis, conformational analysis, immunosuppressive and glycosidase inhibitory activity studies   SCI SCIE

    Bhuma, Naresh (Department of Chemistry, Garware Research Centre, Savitribai Phule Pune University (Formerly University of Pune), Pune, 411007, India ) , Burade, Sachin S. (Department of Chemistry, Garware Research Centre, Savitribai Phule Pune University (Formerly University of Pune), Pune, 411007, India ) , Louat, Thierry (KU Leuven, Interface Valorisation Platform (IVAP), Kapucijnenvoer 33, 3000, Leuven, Belgium ) , Herman, Jean (KU Leuven, Interface Valorisation Platform (IVAP), Kapucijnenvoer 33, 3000, Leuven, Belgium ) , Kawade, Sonali (Department of Bio-Chemistry, Savitribai Phule Pune University (Formerly University of Pune), Pune, 411007, India ) , Doshi, Pooja J. (Department of Bio-Chemistry, Savitribai Phule Pune University (Formerly University of Pune), Pune, 411007, India ) , Dhavale, Dilip D. (Department of Chemistry, Garware Research Centre, Savitribai Phule Pune University (Formerly University of Pune), Pune, 411007, India)
    Tetrahedron v.74 no.8 ,pp. 852 - 858 , 2018 , 0040-4020 ,

    초록

    Abstract The fluorinated piperidine iminosugars 2a-4a and their N -octyl and N -decyl derivatives 2b,c-4b,c were synthesized from D -mannose/ D -xylose using nucleophilic fluorination as the key step. The conformation of iminosugars 2 / 3 , either 2 C 5 or 5 C 2 , was assigned based on the 1 H NMR studies at different pH. Immunomodulatory activity of 2a,c-4a,c was examined using Mixed Lymphocyte Reaction (MLR) and B-cell assay. The N -alkylated fluorinated D - manno -iminosugars 3b/4b were found to be better immunosuppressive agents (IC 50 = 5–6 μ M) on T-cells. The fluorinated iminosugar 3a/4a act as potent and selective inhibitors of β -glucosidase (IC 50 = 4–8 μ M). The N -alkyl-iminosugars 4b-c were found to be moderate inhibitors of α -glucosidase (yeast) and α -galactosidase (coffee beans), respectively. Highlights Synthesis of mono- and gem-difluorinated piperidine iminosugars and their N-octyl and N-decyl derivatives in a less number of steps. Introduction of mono- and gem di-fluorine achieved by using DAST (nucleophilic fluorinataing agent) in high yields. Conformation of iminosugars, either 2 C 5 or 5 C 2 , was assigned based on the 1 H NMR studies at different pH. Immunosupressive activity evaluated in vitro by MLR assay and B-cell assay. Glycosidase inhibitory activity study of mono- and gem-difluorinated piperidine-iminosugars is described. Graphical abstract [DISPLAY OMISSION]

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  2. [해외논문]   Bioactive compounds from the scale insect fungus Conoideocrella tenuis BCC 44534   SCI SCIE

    Saepua, Siriporn (Corresponding author.) , Kornsakulkarn, Jittra , Somyong, Wiwat , Laksanacharoen, Pattiyaa , Isaka, Masahiko , Thongpanchang, Chawanee
    Tetrahedron v.74 no.8 ,pp. 859 - 866 , 2018 , 0040-4020 ,

    초록

    Abstract Eleven new compounds, including two quinone derivatives of bioxanthracene, conoideocrellones A ( 1 ) and B ( 2 ), two bioxanthracenes 3 and 4 , four isocoumarins and isocoumarin glycosides 7 – 10 , two phenolic compounds 16 and 17 , and a diterpenoid compound, conoideocin A ( 18 ), were isolated from culture of the scale-insect pathogenic fungus Conoideocrella tenuis BCC 44534. Seventeen known compounds, compounds 5 and 6 , ES-242-2 and its atropisomer, isocoumarins and isocoumarin glycosides 11 – 15 , 3,4,6-trihydroxymellein, cis -4,6-dihydroxymellein, metarhizins A ( 19 ) and B ( 20 ), BR-050 ( 21 ), 5 α ,8 α -epidioxy-24( R )-methylcholesta-6,22-dien-3 β -ol, zeorin, and conoideocrellide A, were also isolated from this fungus. Structures of these compounds were elucidated by NMR and MS data analyses. Compound 4 was active against Plasmodium falciparum K1 (IC 50 6.6 μg/mL), while it did not show cytotoxicity. Conoideocrellone A ( 1 ) and compounds 3 and 7 exhibited cytotoxic activity, while conoideocin A ( 18 ) showed broad range of biological activities including antimalarial, antibacterial, and cytotoxic activities. Graphical abstract [DISPLAY OMISSION]

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    회원님의 원문열람 권한에 따라 열람이 불가능 할 수 있으며 권한이 없는 경우 해당 사이트의 정책에 따라 회원가입 및 유료구매가 필요할 수 있습니다.이동하는 사이트에서의 모든 정보이용은 NDSL과 무관합니다.

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  3. [해외논문]   Access to the enantiopure pyrrolobenzodiazepine (PBD) dilactam nucleus via self-disproportionation of enantiomers   SCI SCIE

    Abá (Laboratory of Organic Chemistry and Laboratory of Medicinal Chemistry (Associated Unit to CSIC), Department of Pharmacology, Toxicology and Medicinal Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII 27-31, E-08028, Barcelona, Spain ) , s, Sò (Laboratory of Organic Chemistry and Laboratory of Medicinal Chemistry (Associated Unit to CSIC), Department of Pharmacology, Toxicology and Medicinal Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII 27-31, E-08028, Barcelona, Spain ) , nia (Institut de Ciència de Materials de Barcelona (ICMAB-CSIC), Campus UAB, 08193, Cerdanyola, Spain ) , Arró (Laboratory of Organic Chemistry and Laboratory of Medicinal Chemistry (Associated Unit to CSIC), Department of Pharmacology, Toxicology and Medicinal Chemistry, Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan) , niz, Carlos , Molins, Elies , Escolano, Carmen
    Tetrahedron v.74 no.8 ,pp. 867 - 871 , 2018 , 0040-4020 ,

    초록

    Abstract A short synthesis of an enantiopure pyrrolobenzodiazepine (PBD) dilactam featuring early installation of the C2-C3 unsaturation is reported. An enantioselective cooperative catalytic cascade followed by self-disproportionation of enantiomers via sublimation afforded the enantiopure 2,3-dihydro-1 H -pyrrole key intermediate, 1 . N -Acylation followed by reduction and lactam formation furnished the PBD dilactam. Graphical abstract [DISPLAY OMISSION]

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  4. [해외논문]   10-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-methyl-1H,10H-pyrano[4,3-b] chromen-1-ones from a pseudo-multicomponent reaction and evaluation of their antioxidant activity   SCI SCIE

    Saher, Liza (Lab. de Physique Chimie des Materiaux (LPCM), Département de Chimie, Faculté) , Makhloufi-Chebli, Malika (des Sciences, Université) , Dermeche, Leila (Mouloud Mammeri, 15000, Tizi Ouzou, Algeria ) , Dermeche, Samia (Lab. de Physique Chimie des Materiaux (LPCM), Département de Chimie, Faculté) , Boutemeur-Khedis, Baya (des Sciences, Université) , Rabia, Cherifa (Mouloud Mammeri, 15000, Tizi Ouzou, Algeria ) , Hamdi, Maamar (Lab. de Physique Chimie des Materiaux (LPCM), Département de Chimie, Faculté) , Silva, Artur M.S. (des Sciences, Université)
    Tetrahedron v.74 no.8 ,pp. 872 - 879 , 2018 , 0040-4020 ,

    초록

    Abstract A series of novel 10-(4-hydroxy-6-methyl-2-oxo-2 H -pyran-3-yl)-3-methyl-1 H ,10 H -pyrano[4,3- b ]chromen-1-ones were synthesized by a pseudo-three-component reaction of 4-hydroxy-6-methyl-2-oxo-2 H -pyran-2-one (TAL) with 2-hydroxyarylaldehydes using different acids as catalysts and solvents. The approach relies on a regioselective cascade reaction involving two molar equiv of the TAL iteratively acting as active methylene in a Knoevenagel condensation and in a Michael addition. The antioxidant activity of the synthesized compounds were determined using the DPPH scavenging assay, being the results dependent on the nature and number of chromone substituents. The compound bearing an ortho -dihydroxy (catechol) moiety showed excellent activity at lower concentrations, while derivatives bearing alkoxy groups as substituents present pro-oxidant activity. Graphical abstract [DISPLAY OMISSION]

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  5. [해외논문]   Solution conformations for the flexible 1-chloro-1,1-difluoro-2-pentanol unveiled using multinuclear magnetic resonance   SCI SCIE

    Martins, Francisco A. (Department of Chemistry, Federal University of Lavras, 37200-000, Lavras, MG, Brazil ) , Zeoly, Lucas A. (Institute of Chemistry, University of Campinas, 13083-970, Campinas, SP, Brazil ) , Cormanich, Rodrigo A. (Institute of Chemistry, University of Campinas, 13083-970, Campinas, SP, Brazil ) , Freitas, Matheus P. (Department of Chemistry, Federal University of Lavras, 37200-000, Lavras, MG, Brazil)
    Tetrahedron v.74 no.8 ,pp. 880 - 883 , 2018 , 0040-4020 ,

    초록

    Abstract The preferred conformations of a small polyfunctional molecule containing fluorine, chlorine and hydroxyl groups, the 1-chloro-1,1-difluoro-2-pentanol ( CDP ), were completely elucidated using 1 H, 13 C and 19 F NMR in three different solvents. While the Cl-C-C-O dihedral angle was asserted using coupling constant data for the diastereotopic fluorines, the Et-C-C-O torsional angle was analyzed by means of 1 H NMR spectra with selective irradiation of the diastereotopic hydrogens and fluorines. In addition, unusual couplings of the hydroxyl hydrogen with a diastereotopic hydrogen and fluorines provided information on the O-H orientation. The behavior of 1 J C,F when the solvents varied agrees with a weak F⋅⋅⋅HO intramolecular hydrogen bond. These findings were corroborated, and the governing interactions rationalized with the aid of high level CCSD(T) theoretical calculations. Noteworthy, hyperconjugation involving the electron-acceptor σ* C-Cl orbital drives the conformational equilibrium rather than the fluorine gauche effect. Graphical abstract [DISPLAY OMISSION]

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    NDSL에서는 해당 원문을 복사서비스하고 있습니다. 아래의 원문복사신청 또는 장바구니담기를 통하여 원문복사서비스 이용이 가능합니다.

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  6. [해외논문]   New bioactive pyrrospirones C−I from a marine-derived fungus Penicillium sp. ZZ380   SCI SCIE

    Song, Tengfei (Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, PR China ) , Chen, Mengxuan (Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, PR China ) , Chai, Weiyun (Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, PR China ) , Zhang, Zhizhen (Ocean College, Zhoushan Campus, Zhejiang University, Zhoushan 316021, PR China ) , Lian, Xiao-Yuan (College of Pharmaceutical Sciences, Zhejiang University, Hangzhou 310058, PR China)
    Tetrahedron v.74 no.8 ,pp. 884 - 891 , 2018 , 0040-4020 ,

    초록

    Abstract Seven rare pyrrospirones C−I ( 1 – 7 ) as well as 18 known compounds were isolated from a marine-derived fungus Penicillium sp. ZZ380. Structures of the new pyrrospirones were elucidated by extensive NMR spectroscopic analyses, HRESIMS data, and Mosher's method. Pyrrospirone D ( 2 ) was also confirmed by X-ray diffraction analysis. Pyrrospirone G ( 5 ) showed potent activity in inhibiting the proliferation of different glioma cells with IC 50 values of 1.06–8.52 μM and pyrrospirones C ( 1 ), F ( 4 ), and I ( 7 ) had antimicrobial activity against the growth of both methicillin-resistant Staphylococcus aureus and Escherichia coli with MIC values of 2.0–5.0 μg/mL. Highlights Pyrrospirones C−I were isolated from a marine-derived fungus Penicillium sp. Pyrrospirones C−I are rare alkaloids. Pyrrospirone G showed potent activity against different glioma cells. Pyrrospirones C, F, and I had antimicrobial activity. Graphical abstract [DISPLAY OMISSION]

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    NDSL에서는 해당 원문을 복사서비스하고 있습니다. 아래의 원문복사신청 또는 장바구니담기를 통하여 원문복사서비스 이용이 가능합니다.

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  7. [해외논문]   Synthesis and antiproliferative evaluation of glucosylated pyrazole analogs of K252c   SCI SCIE

    Douara, Bachir (Université) , Esvan, Yannick J. (Clermont Auvergne, CNRS, ICCF, F-63000 Clermont-Ferrand, France ) , Pereira, Elisabeth (Université) , Giraud, Francis (Clermont Auvergne, CNRS, ICCF, F-63000 Clermont-Ferrand, France ) , Volodina, Yulia L. (Université) , Kaluzhny, Dmitry N. (Clermont Auvergne, CNRS, ICCF, F-63000 Clermont-Ferrand, France ) , Shtil, Alexander A. (Université) , Anizon, Fabrice (Clermont Auvergne, CNRS, ICCF, F-63000 Clermont-Ferrand, France ) , Moreau, Pascale (Blokhin National Medical Center of Oncology, 115478 Moscow, Russian Federation )
    Tetrahedron v.74 no.8 ,pp. 892 - 901 , 2018 , 0040-4020 ,

    초록

    Abstract Pyrazole analogs of the staurosporine aglycon K252c were recently described as potent inhibitors of the three Pim protein kinase isoforms. To evaluate the impact of the introduction of a sugar moiety on the biological activities of this heterocyclic scaffold, four new glucosylated pyrazole analogs of K252c were synthesized. Their biological evaluation demonstrated that most active compounds 11 and 19 substituted by a β- D -glucosyl moiety at N12 or N13 positions exhibited antiproliferative activities toward HCT116 cells. Graphical abstract [DISPLAY OMISSION]

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  8. [해외논문]   Structure elucidation of phenoxathiin-based thiacalix[4]arene conformations using NOE and RDC data   SCI SCIE

    Landovský (Department of Organic Chemistry, University of Chemistry and Technology (UCT) Prague, Technická) , , Tomá (5, 166 28 Prague 6, Czech Republic ) , š (Laboratory of NMR Spectroscopy, UCT Prague, Technická) , (5, 166 28 Prague 6, Czech Republic ) , Tichotová (Laboratory of NMR Spectroscopy, UCT Prague, Technická) , , Marké (5, 166 28 Prague 6, Czech Republic ) , ta (Department of Organic Chemistry, University of Chemistry and Technology (UCT) Prague, Technická) , Vrzal, Luká (5, 166 28 Prague 6, Czech Republic ) , š (Department of Solid State Chemistry, UCT Prague, Technická) , (5, 166 28 Prague 6, Czech Republic ) , Budka, Jan (Laboratory of NMR Spectroscopy, UCT Prague, Technická) , Eigner, Vá (5, 166 28 Prague 6, Czech Republic ) , clav (Department of Organic Chemistry, University of Chemistry and Technology (UCT) Prague, Technická) , Dvoř (5, 166 28 Prague 6, Czech Republic) , á , ková , , Hana , Lhotá , k, Pavel
    Tetrahedron v.74 no.8 ,pp. 902 - 907 , 2018 , 0040-4020 ,

    초록

    Abstract Phenoxathiin-based thiacalix[4]arene, obtained by the acid-catalysed rearrangement of the corresponding spirodienone derivative, was immobilized using the alkylation with chloroacetonitrile to yield three (out of four theoretically possible) stereoisomers. As the conformational outcome of the reaction could not be unambiguously assigned using standard NMR techniques, the method of Residual Dipolar Coupling constants (RDCs) was applied. The measuring of an anisotropic through-space dipole-dipole interactions in the lyotropic liquid crystalline alignment medium (PELG, poly-γ-ethyl- L -glutamate, and PBLG, poly-γ-benzyl- L -glutamate) enabled the assignment of the individual conformers. The usefulness of this approach was finally confirmed by the X-ray crystallography data. Graphical abstract [DISPLAY OMISSION]

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