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  • 1.
    Acharya, P
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    Chattopadhyaya, J
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    The Hydrogen Bonding and Hydration of 2'-OH in Adenosine and Adenosine 3'-ethylphosphate.2002In: J. Org. Chem., Vol. 67, p. 1852-1865Article in journal (Refereed)
  • 2.
    Amirkhanov, N V
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    Chattopadhyaya, J
    The RNase H Affinity and Cleavage of the target RNA in the Antisense-RNA Hybrid Duplexes Containing various 3’-Tethered Substituents in the Antisense Strand.2002In: J. Chem. Soc. Perkin 2, Vol. 2, p. 271-281Article in journal (Refereed)
  • 3.
    Amirkhanov, N V
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    Pradeepkumar, P I
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    Chattopadhyaya, J
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Faculty of Science and Technology, Biology, Department of Bioorganic Chemistry.
    Kinetic Analysis of the RNA Cleavage of the oxetane modified Antisense-RNA Hybrid Duplex by RNase H.2002In: J. Chem. Soc. Perkin 2, Vol. 5, p. 976-984Article in journal (Refereed)
  • 4. Bengtson, A
    et al.
    Hallberg, A
    Larhed, M
    Fast synthesis of aryl triflates with controlled microwave heating2002In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 4, no 7, p. 1231-1233Article in journal (Refereed)
    Abstract [en]

    [GRAPHICS] Synthesis of aryl triflates from phenols using N-phenyltriflimide requires only 6 min for completion when conducted with controlled microwave heating. The methodology was applied to both solution- and solid-phase conditions. Ten different aryl triflates were synthesized and isolated in good yields. Applications in high-throughput chemistry are suggested.

  • 5. Bengtson, A
    et al.
    Larhed, M
    Hallberg, A
    Protected indanones by a Heck-Aldol annulation reaction2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 16, p. 5854-5856Article in journal (Refereed)
    Abstract [en]

    Monoprotected 3-hydroxyindan-1-ones have been prepared in moderate to good yields by a new tandem reaction involving salicylaldehyde triflates and commercially available 2-hydroxyethyl vinyl ether. This one-pot annulation reaction proceeds in the presence of a palladium bidentate catalyst and results in the formation of two new ring systems.

  • 6.
    Berlin, S.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Ericsson, C
    Engman, L
    Construction of Tetrahydrofuran-3-ones from Readily Available Organochalcogen Precursors via Radical Carbonylation/Reductive Cyclization2002Article in journal (Other scientific)
  • 7.
    Bertilsson, Sophie
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Asymmetric base-promoted epoxide rearrangement: achiral lithium amides revisited2002In: Tetrahedron, no 58, p. 4665-4668Article in journal (Refereed)
  • 8.
    Bertilsson, Sophie
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Södergren, Mikael
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    New Catalysts for the Base-Promoted Isomerization of Epoxides to Allylic Alcohols. Broadened Scope and Near-Perfect Asymmetric Induction2002In: J. Org. Chem., no 67, p. 1567-1573Article in journal (Refereed)
  • 9.
    Besev M, Engman L,
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Diastereocontrol by Hydroxyl Auxiliary in the Synthesis of Pyrrolidines via Radical Cyclization2002In: Org. Lett., no 4, p. 3023-Article in journal (Other scientific)
  • 10.
    Beşev, Magnus
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    Radical Cyclization Approaches to Pyrrolidines2002Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Five-membered rings are readily prepared by 5-exo-trig radical cyclization. This thesis is concerned with novel methodology for pyrrolidine synthesis. We have synthesised selenium containing radical precursors from aziridines and α-phenylseleno ketones, and cyclized them to 2,4- and 3,4-disubstituted pyrrolidines. A few examples of 5-exo-dig cyclization were also demonstrated. In another study we investigated the capacity of the nitrogen protecting group to direct diastereoselectivity in the formation of 2,4-disubstituted pyrrolidines. The diphenylphosphinoyl protecting group directed cyclization to occur in a highly cis-selective manner. When cyclizations were performed at 17 oC, cis/trans-ratios as high as 24/1 were obtained. In contrast, cyclization of the unprotected pyrrolidine precursor afforded the trans-diastereomer as the major product (cis/trans = 1/3.3 – 1/20). We also examined the use of a hydroxyl auxiliary for controlling diastereoselectivity in radical cyclization. The required selenium containing radical precursors were synthesised from 2-cyanoaziridines by addition of organometallic reagents, reduction of the resulting aziridine ketone, and benzeneselenol ring-opening of the aziridine. Cyclization at 17 oC produced 2,4-disubstituted pyrrolidines substantially enriched in the trans-isomer (cis/trans = 1/9 – 1/12). Novel radical cyclization approaches to thiazolines and pyrrolines were also tried.

    The thesis also describes attempts to improve the Hassner aziridine synthesis by employing stannous chloride as a functional group tolerant reducing agent.

  • 11.
    Bohl Kullberg, Erika
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Bergstrand, Nill
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical Chemistry.
    Carlsson, Jörgen
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Edwards, Katarina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical Chemistry.
    Johnsson, Markus
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Physical Chemistry.
    Sjöberg, Stefan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gedda, Lars
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Medicine, Department of Oncology, Radiology and Clinical Immunology, Biomedical Radiation Sciences.
    Development of EGF-conjugated liposomes for targeted delivery of boronated DNA-binding agents2002In: Bioconjugate chemistry, ISSN 1043-1802, E-ISSN 1520-4812, Vol. 13, no 4, p. 737-743Article in journal (Refereed)
    Abstract [en]

    Liposomes are of interest as drug delivery tools for therapy of cancer and infectious diseases. We investigated conjugation of epidermal growth factor, EGF, to liposomes using the micelle-transfer method. EGF was conjugated to the distal end of PEG−DSPE lipid molecules in a micellar solution and the EGF−PEG−DSPE lipids were then transferred to preformed liposomes, either empty or containing the DNA-binding compound, water soluble acridine, WSA. We found that the optimal transfer conditions were a 1-h incubation at 60 °C. The final conjugate, 125I-EGF−liposome−WSA, contained approximately 5 mol % PEG, 10−15 EGF molecules at the liposome surface, and 104 to 105 encapsulated WSA molecules could be loaded. The conjugate was shown to have EGF-receptor-specific cellular binding in cultured human glioma cells.

  • 12.
    Borbath, I
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Gregoire, V
    Bergström, M
    Laryea, D
    Långström, B
    P.S,
    Use of 5-[(76)Br]bromo-2'-fluoro-2'.deoxyuridine as a ligand for tumour proliferation: validation in an animal tumour model2002In: Eur. J. Nucl. Med. Mol. Imaging, Vol. 1, no 29, p. 19-27Article in journal (Other scientific)
  • 13. Brandt, Peter
    et al.
    Norrby, Per-Ola
    Daly, Adrian M
    Gilheany, Declan G
    Chromium-salen-mediated alkene epoxidation: a theoretical and experimental study indicates the importance of spin-surface crossing and the presence of a discrete intermediate.2002In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 8, no 18, p. 4299-307Article in journal (Refereed)
    Abstract [en]

    The mechanism of alkene epoxidation by chromium(v) oxo salen complexes has been studied by DFT and experimental methods. The reaction is compared to the closely related Mn-catalyzed process in an attempt to understand the dramatic difference in selectivity between the two systems. Overall, the studies show that the reactions have many similarities, but also a few critical differences. In agreement with experiment, the chromium system requires a change from low- to high-spin in the catalytic cycle, whereas the manganese system can proceed either with spin inversion or entirely on the high-spin surface. The low-spin addition of metal oxo species to an alkene leads to an intermediate which forms epoxide either with a barrier on the low-spin surface or without a barrier after spin inversion. Supporting evidence for this intermediate was obtained by using vinylcyclopropane traps. The chromium(v) oxo complexes can adopt a stepped shape or form a more concave surface, analogous to previous results on manganese salen complexes.

  • 14.
    Bregadze V, Sivaev I, Sjöberg S
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Synthesis of Functional Derivatives of Cobalt Bis(1,2-dicarolide) Anion for BNCT.2002In: Research and Development in Neutron Capture Therapy, p. 13-17Article in journal (Other scientific)
  • 15.
    Ekegren, Jenny
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Synthesis of New Chiral N, S- and N, O-Ligands. Evaluation in Asymetric Transfer Hydrogenation2002Licentiate thesis, monograph (Other scientific)
  • 16.
    Ekegren, Jenny
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Modin, Stefan
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Alonso, Diego
    Andersson, Pher
    Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Multigram scale synthesis of a useful aza-Diels-Alder adduct in a one-step procedure2002In: Tetrahedron Asymmetry, no 13, p. 447-449Article in journal (Refereed)
  • 17.
    El-Sayed, I .
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Guliashvili, T.
    Hazell, R.
    Gogoll, A.
    Ottosson, H.
    Evidence for Formation of Silenes Strongly Influenced by Reversed Si=C Bond Polarity2002In: Organic LettersArticle in journal (Other scientific)
  • 18.
    Engman, L.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Kania, I.
    Oleksyn, B.J.
    Sliwinski, J.
    Wojton, A.J.
    Intermolecular Interactions in the Crystalline State of some Organotellurium Antioxidants2002Article in journal (Other scientific)
  • 19.
    Erdelyi, Mate
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Rapid microwave-assisted solid phase peptide synthesis2002In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 11, p. 1592-1596Article in journal (Refereed)
    Abstract [en]

    A microwave-assisted, rapid solid phase peptide synthesis procedure is presented. It has been applied to the coupling of sterically hindered Fmoc-protected amino acids yielding di- and tripeptides. Optimized conditions for a variety of coupling reagents are reported. Peptides were obtained rapidly (1.5-20 min) and without racemization.

  • 20.
    Erdélyi, M
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Gogoll, A
    Rapid Microwave-Assisted Solid Phase Peptide Synthesis.2002In: Synthesis, p. 1592-Article in journal (Other scientific)
  • 21.
    Erdélyi, M
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Langer, V
    Karlén, A
    Gogoll, Adolf
    Insight into B-Hairpin Stability: A Structural and Thermodynamic Study of Diastereomeric B-Hairpin Mimetics2002In: New J. Chem., no 26, p. 834-Article in journal (Other academic)
  • 22.
    Erdélyi, Máté
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Development of new mimetics for b-hairpins. Synthesis, structure and conformation2002Licentiate thesis, monograph (Other scientific)
  • 23.
    Eriksson L, Beletskaya I.P, Bregadze V.I, Sivaev I.B, Sjöberg S.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Palladium-catalyzed cross-coupling reactions of arylboronic acids and 2-I-p-carborane2002In: Journal of Organometallic Chemistry, no 657, p. 267-272Article in journal (Other scientific)
  • 24.
    Fogarty, H. A.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Tsuji, H.
    David, D. E.
    Ottosson, C-H.
    Ehara, M.
    Nakatsuji, H.
    Tamao, K.
    Michl, J.
    Peralkylated Tetrasilanes: Conformational Dependence of the Photoelectron Spectrum2002In: J. Phys. Chem. A;, no 106(10), p. 2369-2373Article in journal (Other scientific)
  • 25.
    Gayet, Arnaud
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bertilsson, Sophie
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Novel Catalytic Kinetic Resolution of Racemic Epoxides to Allylic Alcohols2002In: Organic Letters, Vol. 4, no 22, p. 3777-3779Article in journal (Refereed)
  • 26. Hagberg, GE
    et al.
    Torstensson, R
    Marteinsdottir, I
    Uppsala University, Medicinska vetenskapsområdet, Faculty of Medicine, Department of Neuroscience.
    Fredriksson, M
    Långström, B
    Blomquist, G
    Kinetic compartment modelling supports the use of (11C)-5-hydroxy-L-tryptophan for PET assessment of serotonin synthesis in human brain.2002In: J Cereb Blood Flow Metab, Vol. 22, p. 1352-Article in journal (Refereed)
  • 27.
    Hansson, M
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Arvidsson, P.I
    Nilsson, Lill S.O
    Ahlberg, P.
    3Stereoselective Solvent Induced 1,3-proton Transfer of an Allylic Alkoxide to a Homoallylic Alkoxide Catalyzed by a Chiral Lithium Amide22002In: Perkin Trans. 2, p. 763-767Article in journal (Other scientific)
  • 28.
    Hartvig, P
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Bergström, M
    Antoni, Gunnar
    Långström, B.
    Positron Emission Tomography and brain Monoamine neurotransmission-Entries for study drug interactions2002In: Current Pharmaceutical Design, no 8, p. 1417-1434Article in journal (Other academic)
  • 29.
    Hartvig, P
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Nordberg, A
    Torstensson, R
    Sjöberg, P
    Fasth, K-J
    Långström, B.
    Interactions of a muscarinic cholinergic agonist with acetylcholine and dopamine receptors in the monkey brain studied by PET2002In: Dementia and Genetic Cognitive Disorders, no 13, p. 199-204Article in journal (Other scientific)
  • 30.
    Hilmersson, G
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Davidsson, Ö
    Arvidsson, P.I.
    2On the Mechanism of Internal ortho-Lithiation in a Mixed Complex Between n-BuLi and a Chiral Lithium Amide22002In: Helv. Chim. Acta, no 85, p. 3814-3822Article in journal (Other scientific)
  • 31. Janosik, T
    et al.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Oxidative coupling of indoline-2-thione or oxindole: Formation of cyclic and acyclic indole trimers2002In: Heterocycles, ISSN 0385-5414, E-ISSN 1881-0942, Vol. 57, no 7, p. 1273-1278Article in journal (Refereed)
    Abstract [en]

    Oxidation of indoline-2-thione using p-toluenesulfonyl azide produced a modest yield of the structurally novel cyclic sulfur containing indole trimer (12). In contrast, the oxidation of oxindole with iodine instead produced an acyclic trimeric indole derivative.

  • 32.
    Janosik, Tomasz
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Romero, Ivan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institute.
    Stensland, B
    Stålhandske, C
    Marques, M M B
    Santos, M M M
    Lobo, A M
    Prabhakar, S
    Duarte, M F
    Florencio, M H
    Synthetic, spectroscopic, and X-ray crystallographic studies of [1,2,7,8]tetrathiacyclododecino[4,3-b: 5,6-b': 10,9-b": 11,12-b''']tetraindoles2002In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 8, p. 1392-1396Article in journal (Refereed)
    Abstract [en]

    Two conformationally different [1,2,7,8]tetrathiacyclododecino[4,3-b:5,6-b':10,9-b":11,12-b''']tetraind oles 9a and 9b have been isolated in good yields, and the existence of a third conformer 9c in solution was demonstrated by mass spectrometry and H-1 NMR spectroscopy. The interconversions of the tetraindoles 9a-c have also been studied. The conformation of 9b was confirmed by X-ray crystallography, while the conformations of 9a and 9b were assigned on the basis of spectroscopic data, and were also supported by molecular modelling studies. In addition, the elusive dithiin 3 was isolated and the structure was proven by X-ray crystallography.

  • 33.
    Janosik, Tomasz
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Johnson, Ann-Louise
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Synthesis of the marine alkaloids rhopaladins A, B, C and D2002In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 14, p. 2813-2819Article in journal (Refereed)
    Abstract [en]

    The total synthesis of all four known rhopaladins, A-D, isolated from the Okinawan marine tunicate Rhopalaea sp., in two synthetic steps is described, involving an imidate based cyclization with tryptophan esters as the key step to afford the appropriately substituted imidazolinone unit. A short and efficient new synthesis of indol-3-yl-carbonyl nitriles from indol-3-yl-carboxaldehydes and trimethylsilyl cyanide, followed by oxidation with DDQ is also described.

  • 34.
    Janosik, Tomasz
    et al.
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Stensland, B
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap. Karolinska Institutet.
    Sulfur-rich heterocycles from 2-metalated benzo[b]thiophene and benzo[b]furan: Synthesis and structure2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 17, p. 6220-6223Article in journal (Refereed)
    Abstract [en]

    The reaction of 2-lithiated benzo[b]thiophene with 8 equiv of elemental sulfur was found to give pentathiepino[6,7-b]benzo[d]thiophene. In contrast, treatment of 2-lithiated benzo[b]furan with sulfur under similar conditions produced the interesting ring system bis(benzo[4,5]-furo)[2,3-e:3',2'-g][1,2,3,4]tetrathiocine. Both of these new cyclic polysulfides were studied by X-ray crystallography. Two polymorphic forms of pentathiepino[6,7-b]benzo[d]thiophene were found, displaying similar conformations but different packing schemes, which was also evident from powder diffraction data.

  • 35.
    Jia, Z. S.
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Ottosson, H.
    Zeng, X.
    Thibblin, A.
    The Role of Ion-Molecule Pairs in Solvolysis Reactions. Nucleophilic Addition of Water to a Tertiary Allylic Carbocation2002In: J. Org. Chem, no 67 (1), p. 182-187Article in journal (Other scientific)
  • 36.
    Jia, Z.S
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Rudzinski, J.
    Paneth, P.
    Thibblin, A.
    Borderline between E1cB and E2 Mechanisms. Chlorine Isotope Effects in Base-Promoted Elimination Reactions2002Article in journal (Other scientific)
  • 37.
    Johannesson, Petra
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry.
    Lindeberg, Gunnar
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Johansson, Anja
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Nikiforovich, Gregory V
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Synnergren, Barbro
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Le Greves, Madeleine
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.
    Nyberg, Fred
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences, Biological Research on Drug Dependence.
    Karlen, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Vinyl sulfide cyclized analogues of angiotensin II with high affinity and full agonist activity at the AT(1) receptor2002In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 45, no 9, p. 1767-1777Article in journal (Refereed)
    Abstract [en]

    Vinyl sulfide cyclized analogues of the octapeptide angiotensin II that are structurally related to the cyclic disulfide agonist c[Hcy(3,5)]Ang II have been prepared. The synthesis relies on the reaction of the mercapto group of a cysteine residue in position 3 with the formyl group of allysine incorporated in position 5 of angiotensin II. A mixture of the cis and the trans isomers was formed, and these were separated and isolated by RP-HPLC. Thus, the three-atom CH(2)[bond]S[bond]S element of the AT(1) receptor agonist c[Hcy(3,5)]Ang II has been displaced by a bioisosteric three-atom S[bond]CH[double bond]CH element. A comparative conformational analysis of the 13-membered ring systems of c[Hcy(3,5)]Ang II and the 13-membered cyclic vinyl sulfides with cis and trans configuration, respectively, suggested that all three systems adopted very similar low-energy conformations. This similarity was also reflected in the bioactivity. Both of the compounds that contained the ring systems encompassing the cis or trans vinyl sulfide elements between positions 3 and 5 exhibited K(i) values less than 2 nM and exerted full agonism at the AT(1) receptor. In contrast, vinyl sulfide cyclization involving the amino acid residues 5 and 7 rendered inactive compounds. The cyclic vinyl sulfides that have agonist activity were both shown to possess low-energy conformers compatible with the previously proposed 3D model for the bioactive conformation of Ang II.

  • 38. Johnson, A L
    et al.
    Janosik, T
    Bergman, Jan
    Södertörn University, Avdelning Naturvetenskap.
    Synthesis of the diketopiperazine dipodazine2002In: ARKIVOC, ISSN 1551-7004, E-ISSN 1551-7012, p. 57-61Article in journal (Refereed)
    Abstract [en]

    The diketopiperazine derivative dipodazine (1), isolated from Penicillium dipodomyis, has been synthesized via a stereoselective aldol condensation from N-protected indole-3-carboxaldehyde and 1,4-diacetyl-2,5-piperazinedione (3) in the presence of cesium carbonate.

  • 39. Jonsson, Sandra Y.
    Selective functionalisation of carbon-carbon double bonds: dihydroxylation of olefins by H₂O₂ & transformation of sulfonyl 1,3-dienes2002Doctoral thesis, comprehensive summary (Other academic)
  • 40.
    Jönsson, Daniel
    Stockholm University, Faculty of Science, Department of Neurochemistry and Neurotoxicology.
    Applications of multi-component condensations and development of polyamine synthesis on solid-phase2002Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    Solid-phase synthesis of small non-polymeric molecules has become increasingly important as a tool in the development of pharmacologically active compounds. Of particular interest are the syntheses of compounds with low molecular weight, low polarity and a reduced flexibility of the functional groups, i.e. physiochemical properties typical for the majority of drugs currently in use.

    The first part of this thesis describes the synthesis of polycyclic structures with constrained conformation, by the application of multi-component condensations on solid-phase. The 8-azabicyclo[3.2.1]octan-3-one structure of the tropane alkaloids was synthesized on solid-phase by a modification of the well known Robinson tropinone synthesis. The 3-component reaction was performed with the amino component anchored to a solid support, consisting of polyethyleneglycol-grafted polystyrene. Treatment of the primary amine with 1,3-acetonedicarboxylic acid and excess of succinaldehyde, resulted in high purity of the corresponding tropane derivative. Further derivatization of the resin-bound tropane derivative was performed by reduction of the keto-group and acylation of the hydroxyl-group.

    The oxygen-bridged tetrahydropyridones are relatively complex polycyclic structures, which previously have been synthesized in solution by condensation of primary amines, coumarin-3-carboxylic acid and ketones. In the evaluation of a solid-phase approach of this 3-component condensation, several members of this class of compounds were synthesized with the amine anchored to a solid support. The yield and purity of the products were dependent on the ketones used in the reaction, but the expected products were obtained using both acyclic and cyclic ketones and substituted acetophenones.

    The second part of this thesis describes the development of a solid-phase polyamine synthesis. The polyamines are a class of compounds with a wide range of pharmacological and physiological effects, which are constituents in many types of venoms of wasps and spiders. Synthesis of polyamines in homogenous solution is accompanied with several problems concerning selectivity, work-up and yield. By employing a solid-phase approach, a rapid and convenient method for synthesis of polyamines is achieved. In the developed protocol, acid labile benzhydryls are used as amino-protecting groups. The polyamine backbone is assembled sequentially by reductive alkylation of the protected secondary amine with Fmoc-amino aldehydes. The protecting groups allow the use of excess of aldehyde, to avoid underivatized amines, without the risking dialkaylation of the amines, which occurs during reductive alkylations of primary amines with unhindered aliphatic aldehydes. The versatility of the method is displayed by a convenient synthesis of four analogues of a wasp toxin, philanthotoxin.

  • 41. Kaiser, N F K
    et al.
    Hallberg, A
    Larhed, M
    In situ generation of carbon monoxide from solid molybdenum hexacarbonyl. A convenient and fast route to palladium-catalyzed carbonylation reactions2002In: Journal of combinatorial chemistry, ISSN 1520-4766, E-ISSN 1520-4774, Vol. 4, no 2, p. 109-111Article in journal (Refereed)
  • 42.
    Karimi F, Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Palladium Mediatd Synthesis of [Carboxy-11C] Amides and Hydrazides Using [11C] Carbon monoxide2002In: J. Chem. Soc. Perkin I, p. 2111-2115Article in journal (Other scientific)
  • 43.
    Karimi F, Långström B.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Synthesis of 3-[(2S)-azetidin-2-ylmethoxyl]-5-[11C]-methylpyridine, an analogue of A-85380, via a Stille coupling2002In: Journal Labelled Compounds and Radiopharmaceuticals, no 45, p. 423-434Article in journal (Other scientific)
  • 44.
    Karimi, Farhad
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry, Organic Chemistry.
    [11C]Carbon Monoxide in Palladium- / Selenium-Promoted Carbonylation Reactions: Synthesis of 11C-Imides, Hydrazides, Amides, Carboxylic Acids, Carboxylic Esters, Carbothioates, Ketones and Carbamoyl Compounds2002Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    [11C]Carbon monoxide in low concentrations has been used in palladium- or seleniummediated carbonylation reactions such as the synthesis of 11C-imides, hydrazides, amides, carboxylic acids, esters, carbothioates, ketones and carbamoyl compounds.

    In these reactions aryl iodides have been used in most cases. However, less reactive aryl triflate, chloride and bromides were activated using tetrabutylammonium iodide.

    The reactivities of nucleophiles may have influence on the radiochemical yield of the 11Clabelled compounds. Carboxyamination of aryl halides using aniline derivatives yielded 10% of the corresponding 11C-amide. However, the radiochemical yields increased significantly when the aniline derivatives were treated with lithium bis(trimethylsilyl)amide. In contrast, this reagent did not improve the radiochemical yields when primary amines such as methylamine and benzylamine were used. In these cases the radiochemical yields were improved by using pempidine.

    11C-Esterification usually gave low yields. However, the radiochemical yields of 11C-esters could be improved by using magnesium bromide and pempidine.

    An excess of ligand may have a significant impact on palladium-promoted carbonylation reaction. The radiochemical yields of 11C-ketones were improved when using excess amounts of tri-o-tolylphosphine.

    (13C)Carbon monoxide may be utilized for the synthesis of 13C-substituated compounds in order to confirm the position of 11C-labelling.

  • 45. Kearley, GJ
    et al.
    Johansson, P
    Uppsala University, Interfaculty Units, För teknisk-naturvetenskapliga fakulteten gemensamma enheter, The Studsvik Neutron Research Laboratory. Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Materials Chemistry, Structural Chemistry.
    Delaplane, RG
    Physics, Department of Neutron Research. Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Materials Chemistry, Structural Chemistry.
    Lindgren, Jan
    Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Materials Chemistry, Structural Chemistry. strukturkemi.
    Structure, dynamics and first principles study of diglyme as a model system for poly(ethyleneoxide), PEO2002In: Solid State Ionics: Diffusion & Reactions, Vol. 147, no 3,4, p. 237-Article in journal (Refereed)
  • 46.
    Kjellgren, Johan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Synthesis of stereodefined vinyl-tetrahydropyran and vinyl-octahydrochromene derivatives via acetalization-cyclization of allylsilanes with aldehydes: Origin of the high stereoselectivity2002In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 43, no 6, p. 1123-1126Article in journal (Refereed)
  • 47.
    Kuratsune, H
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry.
    Yamaguti, K
    Lindh, G
    Evengård, B
    Haberg, G
    Matsumura, K
    Iwase, M
    Onoe, H
    Takahashi, M
    Machii, T
    Kanakura, U
    Kitani, T
    Långström, B
    Watanabe, Y
    Brain regions involved in fatigue sensation: Reduced acetylcarnitine uptake into the brain2002In: Neuro Image, no 17, p. 1256-1265Article in journal (Other scientific)
  • 48. Langlet, Abraham
    et al.
    Bergman, Jan
    Wellmar, Ulf
    Bemm, Ulf
    Goede, P.
    Romero, I.
    Lattypov, Nikolaj
    Nitration of 2-substituted pyrimidine-4,6-diones, structure and reactivity of 5,5-gem-dinitropyrimidine-4,6-diones2002In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 67, no 22, p. 7833-7838Article in journal (Refereed)
    Abstract [en]

    Nitration of some 2-substituted pyrimidine-4,6-diones in sulfuric acid was studied, which afforded previously unknown 5,5-gem-dinitropyrimidine-4,6-diones in high yields. The gem-dinitro products were easily attacked by nucleophiles with concomitant formation of gem-dinitroacetyl derivatives, which in turn could be further hydrolyzed to salts of dinitromethane and triureas.

  • 49. Larhed, M
    et al.
    Moberg, C
    Hallberg, A
    Microwave-accelerated homogeneous catalysis in organic chemistry2002In: Accounts of Chemical Research, ISSN 0001-4842, E-ISSN 1520-4898, Vol. 35, no 9, p. 717-727Article, review/survey (Refereed)
    Abstract [en]

    The efficiency of microwave flash heating in accelerating organic transformations (reaction times reduced from days and hours to minutes and seconds) has recently-been proven in several different fields of organic chemistry. This specific account mainly summarizes our own experiences in developing rapid, robust, and selective microwave-assisted transition metal-catalyzed homogeneous reactions. Applications include selective Heck couplings, cross-couplings, and asymmetric substitutions. The science of green chemistry was developed to meet the increasing demand for environmentally benign chemical processes. We believe the combination of metal catalysis and microwave heating will be of importance in the search for green laboratory-scale synthesis.

  • 50.
    Larsson, Andreas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ulicny, Jozef
    Laaksonen, Aatto
    Widmalm, Göran
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Analysis of NMR J couplings in partially protected galactopyranosides*2002In: Organic Letters, ISSN 1523-7052, Vol. 4, no 11, p. 1831-1834Article in journal (Refereed)
    Abstract [en]

    Hydrogen bond mediated NMR J couplings offer additional structural information. The interpretation of these usually small hJ couplings are,however, not necessarily straightforward. In the present case of a carbohydrate system, a four-bond classical W coupling, 4JHO4,H5, is morereasonable on the basis of, in particular, density functional theory calculations of spin-spin coupling constants at the UB3LYP/6-311G** levelof theory.

12 1 - 50 of 98
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