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  • 1. Ahlberg, P.
    et al.
    Karlsson, A.
    Goeppert, A.
    Lill, S. O. N.
    Dinér, P.
    Sommer, J.
    Solvated CH5+ in liquid superacid2001In: Chemistry-a European Journal, Vol. 7, no 9, p. 1936-1943Article in journal (Refereed)
    Abstract [en]

    The transition states for methane activation in liquid superacid have been studied by experimentally determined secondary kinetic deuterium isotope effects (SKIEs) and computational chemistry. For the first time, the SKIEs on hydrogen/deuterium exchange of methane have been measured by using the methane isotopologues in homogeneous liquid superacid ((HF)-H-2/ SbF5). To achieve high accuracy of the SKIEs, the rate constants for pairs of methane isotopologues were simultaneously measured in the same superacid solution by using NMR spectroscopy Density functional theory (DFT and high-level ab initio methods have been employed to model possible intermediates and transition states, assuming that the superacids involved in the exchange reactions are H2F- ions solvated by HF Only the unsolvated superacid H2F- is found to be strong enough to protonate methane. yielding the methonium ion solvated by HF as a potential energy minimum. In contrast, the (HF)(x)-solvated H2F- superacids (x = 1-4) do not appear to be strong enough to yield stable solvated methonium ions. However, such ions show up as parts of the transition slates of the exchange in which the methonium ions are solvated by (HF)(x). The calculated DFT activation barrier is in good agreement with that experimentally observed.

  • 2. Ahlberg, P.
    et al.
    Karlsson, A.
    Goeppert, A.
    Lill, S. O. N.
    Dinér, P.
    Sommer, J.
    Solvated CH5+ in liquid superacid (vol 7, pg 1936, 2001)2001In: Chemistry-a European Journal, Vol. 7, no 12, p. 2501-2501Article in journal (Refereed)
  • 3. Ahlberg, P.
    et al.
    Karlsson, A.
    Goeppert, A.
    Lill, S. O. N.
    Dinér, Peter
    Sommer, J.
    Solvated CH5+ in liquid superacid2001In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 7, no 12, p. 2501-2510Article in journal (Refereed)
  • 4. Alao, John Patrick
    et al.
    Michlíková, Sona
    Dinér, Peter
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Gothenburg University.
    Grøtli, Morten
    Sunnerhagen, Per
    Selective inhibition of RET mediated cell proliferation in vitro by the kinase inhibitor SPP862014In: BMC Cancer, ISSN 1471-2407, E-ISSN 1471-2407, Vol. 14, no 853Article in journal (Refereed)
    Abstract [en]

    Background

    The RET tyrosine kinase receptor has emerged as a target in thyroid and endocrine resistant breast cancer. We previously reported the synthesis of kinase inhibitors with potent activity against RET. Herein, we have further investigated the effect of the lead compound SPP86 on RET mediated signaling and proliferation. Based on these observations, we hypothesized that SPP86 may be useful for studying the cellular activity of RET.

    Methods

    We compared the effects of SPP86 on RET-induced signaling and proliferation in thyroid cancer cell lines expressing RET-PTC1 (TPC1), or the activating mutations BRAFV600E (8505C) and RASG13R (C643). The effect of SPP86 on RET- induced phosphatidylinositide 3-kinases (PI3K)/Akt and MAPK pathway signaling and cell proliferation in MCF7 breast cancer cells was also investigated.

    Results

    SPP86 inhibited MAPK signaling and proliferation in RET/PTC1 expressing TPC1 but not 8505C or C643 cells. In TPC1 cells, the inhibition of RET phosphorylation required co-exposure to SPP86 and the focal adhesion kinase (FAK) inhibitor PF573228. In MCF7 cells, SPP86 inhibited RET- induced phosphatidylinositide 3-kinases (PI3K)/Akt and MAPK signaling and estrogen receptorα (ERα) phosphorylation, and inhibited proliferation to a similar degree as tamoxifen. Interestingly, SPP86 and PF573228 inhibited RET/PTC1 and GDNF- RET induced activation of Akt and MAPK signaling to a similar degree.

    Conclusion

    SPP86 selectively inhibits RET downstream signaling in RET/PTC1 but not BRAFV600E or RASG13R expressing cells, indicating that downstream kinases were not affected. SPP86 also inhibited RET signaling in MCF7 breast cancer cells. Additionally, RET- FAK crosstalk may play a key role in facilitating PTC1/RET and GDNF- RET induced activation of Akt and MAPK signaling in TPC1 and MCF7 cells.

  • 5. Amorati, Riccardo
    et al.
    Valgimigli, Luca
    Dinér, Peter
    Bakhtiari, Khadijeh
    Saeedi, Mina
    Engman, Lars
    Multi-faceted reactivity of alkyltellurophenols towards peroxyl radicals: Catalytic antioxidant versus thiol-depletion effect2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 23, p. 7510-7522Article in journal (Refereed)
    Abstract [en]

    Hydroxyaryl alkyl tellurides are effective antioxidants both in organic solution and aqueous biphasic systems. They react by an unconventional mechanism with ROO. radicals with rate constants as high as 107 M−1 s−1 at 303 K, outperforming common phenols. The reactions proceed by oxygen atom transfer to tellurium followed by hydrogen atom transfer to the resulting RO. radical from the phenolic OH. The reaction rates do not reflect the electronic properties of the ring substituents and, because the reactions occur in a solvent cage, quenching is more efficient when the OH and TeR groups have an ortho arrangement. In the presence of thiols, hydroxyaryl alkyl tellurides act as catalytic antioxidants towards both hydroperoxides (mimicking the glutathione peroxidases) and peroxyl radicals. The high efficiency of the quenching of the peroxyl radicals and hydroperoxides could be advantageous under normal cellular conditions, but pro-oxidative (thiol depletion) when thiol concentrations are low.

  • 6. Amorati, Riccardo
    et al.
    Valgimigli, Luca
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Bakhtiari, Khadijeh
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Saeedi, Mina
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Multi-faceted reactivity of alkyltellurophenols towards peroxyl radicals: Catalytic antioxidant versus thiol-depletion effect2013In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 19, no 23, p. 7510-7522Article in journal (Refereed)
    Abstract [en]

    Hydroxyaryl alkyl tellurides are effective antioxidants both in organic solution and aqueous biphasic systems. They react by an unconventional mechanism with ROO. radicals with rate constants as high as 107M1s1 at 303K, outperforming common phenols. The reactions proceed by oxygen atom transfer to tellurium followed by hydrogen atom transfer to the resulting RO. radical from the phenolic OH. The reaction rates do not reflect the electronic properties of the ring substituents and, because the reactions occur in a solvent cage, quenching is more efficient when the OH and TeR groups have an ortho arrangement. In the presence of thiols, hydroxyaryl alkyl tellurides act as catalytic antioxidants towards both hydroperoxides (mimicking the glutathione peroxidases) and peroxyl radicals. The high efficiency of the quenching of the peroxyl radicals and hydroperoxides could be advantageous under normal cellular conditions, but pro-oxidative (thiol depletion) when thiol concentrations are low.

  • 7. Bertelsen, Søren
    et al.
    Dinér, Peter
    Johansen, Rasmus Lyng
    Jørgensen, Karl Anker
    Asymmetric organocatalytic beta-hydroxylation of alpha, beta-unsaturated aldehydes2007In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 129 1536-1537, no 6, p. 1536-1537Article in journal (Refereed)
    Abstract [en]

    The first catalytic enantioselective β-hydroxylation of α,β-unsaturated aldehydes is presented. Using commercially available (E)-benzaldehyde oxime in the presence of 2-[bis(3,5-bis-trifluoromethyl-phenyl)trimethyl-silanyloxymethyl]pyrrolidine as organocatalyst, the corresponding chiral carbonyl β-oxime ethers are obtained in high yields and with excellent enantioselectivities. These optically active carbonyl and hydroxy β-oxime ethers are highly interesting biological compounds in, e.g., sex pheromone analogues, highly potent antiinflammatory agents, and penicillin and cephalosporin analogues. The chiral carbonyl β-oxime ethers can be reduced to the corresponding 1,3-diols in high yields. Furthermore, the organocatalytic enantioselective β-hydroxylation of α,β-unsaturated aldehydes could be performed on gram scale without loss of enantioselectivity.

  • 8. Bertelsen, Søren
    et al.
    Dinér, Peter
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Johansen, Rasmus Lyng
    Jørgensen, Karl Anker
    Asymmetric organocatalytic beta-hydroxylation of alpha, beta-unsaturated aldehydes2007In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 129, no 6, p. 1536-1537Article in journal (Refereed)
    Abstract [en]

    The first catalytic enantioselective beta-hydroxylation of alpha,beta-unsaturated aldehydes is presented. Using commercially available (E)-benzaldehyde oxime in the presence of 2-[bis(3,5-bis-trifluoromethyl-phenyl)trimethyl-silanyloxymethyl]pyrrolidine as organocatalyst, the corresponding chiral carbonyl beta-oxime ethers are obtained in high yields and with excellent enantioselectivities. These optically active carbonyl and hydroxy beta-oxime ethers are highly interesting biological compounds in, e.g., sex pheromone analogues, highly potent antiinflammatory agents, and penicillin and cephalosporin analogues. The chiral carbonyl beta-oxime ethers can be reduced to the corresponding 1,3-diols in high yields. Furthermore, the organocatalytic enantioselective beta-hydroxylation of alpha,beta-unsaturated aldehydes could be performed on gram scale without loss of enantioselectivity.

  • 9. Bertelsen, Søren
    et al.
    Marigo, Mauro
    Brandes, Sebastian
    Dinér, Peter
    Jørgensen, Karl Anker
    Dienamine catalysis: organocatalytic asymmetric gamma-amination of alpha,beta-unsaturated aldehydes2006In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 128, no 39, p. 12973-12980Article in journal (Refereed)
  • 10. Bertelsen, Søren
    et al.
    Marigo, Mauro
    Brandes, Sebastian
    Dinér, Peter
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Jørgensen, Karl Anker
    Dienamine catalysis: organocatalytic asymmetric gamma-amination of alpha,beta-unsaturated aldehydes2006In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 128, no 39, p. 12973-12980Article in journal (Refereed)
    Abstract [en]

    A new concept in organocatalysis is presented, the direct asymmetric gamma-functionalization of alpha,beta-unsaturated aldehydes. We disclose that secondary amines can invert the usual reactivity of alpha,beta-unsaturated aldehydes, enabling a direct gamma-amination of the carbonyl compound using azodicarboxylates as the electrophilic nitrogen-source. The scope of the reaction is demonstrated for the enantioselective gamma-amination of different alpha,beta-unsaturated aldehydes, giving the products in moderate to good yields and with high enantioselectivities up to 93% ee. Experimental investigations and DFT calculations indicate that the reaction might proceed as a hetero-Diels-Alder cycloaddition reaction. Such a mechanism can explain the "unexpected" stereochemical outcome of the reaction.

  • 11.
    Blomkvist, Björn
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    Dinér, Peter
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry.
    HBF4 center dot DEE-catalyzed formation of sulfinyl imines: Synthesis and mechanistic studies2018In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 59, no 13, p. 1249-1253Article in journal (Refereed)
    Abstract [en]

    A mild acid-catalysed method is reported for the formation of sulfinyl imines from tert-butanesulfinamide and aromatic or aliphatic aldehydes using tetrafluoroboric acid diethyletherate (10 mol%) in dichloromethane. Reactions were performed at room temperature and gave the corresponding sulfinyl imines in excellent yield after 2 h. A DFT study was performed and a mechanism for the reaction is postulated. 

  • 12.
    Blomkvist, Björn
    et al.
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Dinér, Peter
    KTH, School of Engineering Sciences in Chemistry, Biotechnology and Health (CBH), Chemistry, Organic chemistry.
    Mild and Rapid Aniline/HBF4 center dot DEE-Catalysed Formation of Sulfinyl Imines2019In: ChemistrySelect, ISSN 2365-6549, Vol. 4, no 25, p. 7431-7436Article in journal (Refereed)
    Abstract [en]

    The combination of anline and tetrafluoroboric acid diethyl etherate (2.5 mol% and 5 mol%, respectively) significantly accelerates the formation of sulfinyl imines in dichloromethane and isopropylacetate at room temperature compared to previous procedures. A DFT and NMR spectroscopic study shows that the anilinium tetrafluoroborate complex is solvated by sulfinamide molecules in the initial state and that the rate-limiting step of the reaction is the addition of the sulfinamide molecule to the protonated aniline-based imine. In addition, the catalytic system was also utilised in a one-pot, two step reaction, where the in situ formed sulfinyl imine was arylated in a rhodium catalysed reaction with high diastereoselectivity.

  • 13. Diaz-Alvarez, Alba E.
    et al.
    Mesas-Sanchez, Laura
    Dinér, Peter
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Uppsala University, Sweden.
    Access to Optically Pure beta-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst2014In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 19, no 9, p. 14273-14291Article in journal (Refereed)
    Abstract [en]

    The development of new approaches to obtain optically pure beta-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic beta-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic beta-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

  • 14. Dierckx, Anke
    et al.
    Dinér, Peter
    Department of Chemistry, Medicinal Chemistry, University of Gothenburg.
    El-Sagheer, A. H.
    Kumar, Joshi Dhruval
    Brown, T.
    Grøtli, Morten
    Wilhelmsson, Marcus
    Wilhelmsson, L Marcus
    Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA2011In: Nucleic Acids Research, ISSN 0305-1048, E-ISSN 1362-4962, Vol. 34, no 10, p. 4513-4524Article in journal (Refereed)
  • 15. Dierckx, Anke
    et al.
    Dinér, Peter
    University of Gothenburg.
    El-Sagheer, Afaf H
    Kumar, Joshi Dhruval
    Brown, Tom
    Grøtli, Morten
    Wilhelmsson, L Marcus
    Characterization of photophysical and base-mimicking properties of a novel fluorescent adenine analogue in DNA.2011In: Nucleic Acids Research, ISSN 0305-1048, E-ISSN 1362-4962, Vol. 39, no 10, p. 4513-24Article in journal (Refereed)
    Abstract [en]

    To increase the diversity of fluorescent base analogues with improved properties, we here present the straightforward click-chemistry-based synthesis of a novel fluorescent adenine-analogue triazole adenine (A(T)) and its photophysical characterization inside DNA. A(T) shows promising properties compared to the widely used adenine analogue 2-aminopurine. Quantum yields reach >20% and >5% in single- and double-stranded DNA, respectively, and show dependence on neighbouring bases. Moreover, A(T) shows only a minor destabilization of DNA duplexes, comparable to 2-aminopurine, and circular dichroism investigations suggest that A(T) only causes minimal structural perturbations to normal B-DNA. Furthermore, we find that A(T) shows favourable base-pairing properties with thymine and more surprisingly also with normal adenine. In conclusion, A(T) shows strong potential as a new fluorescent adenine analogue for monitoring changes within its microenvironment in DNA.

  • 16.
    Dinér, P.
    et al.
    University of Gothenburg.
    Andersson, T.
    University of Gothenburg.
    Kjellén, J.
    University of Gothenburg.
    Elbing, K.
    University of Gothenburg.
    Hohmann, S.
    University of Gothenburg.
    Grotli, M.
    University of Gothenburg.
    Short cut to 1,2,3-triazole-based p38 MAP kinase inhibitors via [3+2]-cycloaddition chemistry2009In: New Journal of Chemistry, Vol. 33, no 5, p. 1010-1016Article in journal (Refereed)
    Abstract [en]

    A series of 4,5-substituted 1,2,3-triazoles was synthesised via Cu(I)-catalysed azide-alkyne 1,3-dipolar [2 + 3]-cycloaddition reactions followed by a Suzuki coupling. The 1,2,3-triazoles were evaluated as inhibitors of the p38 alpha MAP kinase, showing IC50 values in the high nanomolar range.

  • 17.
    Dinér, P.
    et al.
    University of Gothenburg.
    Pettersen, D.
    University of Gothenburg.
    Nilsson Lill, S. O.
    University of Gothenburg.
    Ahlberg, P.
    University of Gothenburg.
    Investigation of site selectivity of the stereoselective deprotonation of cyclohexene oxide using kinetic resolution of isotopic enantiomers in natural abundance2005In: Tetrahedron-Asymmetry, Vol. 16, no 15, p. 2665-2671Article in journal (Refereed)
    Abstract [en]

    Stereo selective deprotonation of epoxides with lithium arnides can occur by abstraction of protons from more than one site. The site selectivity of the deprotonation of cyclohexene oxide by several chiral and achiral lithium amides has been investigated. H-2 NMR has been used to measure the relative abundances of the isotopomers of the epoxide containing one deuterium. An isotopic stereoisomer, with deuterium in the site undergoing abstraction, reacts slower than its enantiomer and other isotopomers having protium in the same site due to a kinetic isotope effect. This results in a kinetic resolution yielding a relative excess of the less reactive isotopic stereoisomer. Thus, the relative abundance of such an enantiomer increases when compared with those having protium at the site in question as the reaction proceeds. It can be concluded that deprotonation of cyclohexene oxide using some chiral- and non-chiral lithium amides occurs by beta syn-deprotonation. (c) 2005 Elsevier Ltd. All rights reserved.

  • 18.
    Dinér, P
    et al.
    University of Gothenburg.
    Vilg, J VUniversity of Gothenburg.Kjellen, JUniversity of Gothenburg.Iwona, MUniversity of Wroclaw.Andersson, TUniversity of Gothenburg.Hohmann, SUniversity of Gothenburg.Wysocki, RUniversity of Wroclaw .Tamas, M JUniversity of Gothenburg.Grotli, MUniversity of Gothenburg.
    Design, synthesis and characterization of a highly effective Hog1 inhibitor: a powerful tool for analyzing MAP kinase signaling in yeast2010Conference proceedings (editor) (Other academic)
  • 19.
    Dinér, Peter
    University of Gothenburg.
    Alkane activation by superacids and enantioselective reactions with chiral lithium amides: computational and experimental mechanistic studies2005Doctoral thesis, comprehensive summary (Other academic)
  • 20.
    Dinér, Peter
    Department of Chemistry, University of Gothenburg.
    Alkane activation by superacids and enantioselective reactions with chiral lithium amides: computational and experimental mechanistic studies2005Doctoral thesis, comprehensive summary (Other academic)
  • 21.
    Dinér, Peter
    Uppsala University.
    Catalytic asymmetric chiral lithium amide-promoted epoxide rearrangement: a NMR spectroscopic and kinetic investigation2010In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 21, no 21-22, p. 2733-2739Article in journal (Refereed)
  • 22.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Catalytic asymmetric chiral lithium amide-promoted epoxide rearrangement: a NMR spectroscopic and kinetic investigation2010In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 21, no 21-22, p. 2733-2739Article in journal (Refereed)
    Abstract [en]

    The lithium amide derived from the chiral diamine (1R,3S,4S)-3-(1-pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane, has been reported to catalytically deprotonate cyclohexene oxide and other epoxides, yielding chiral allylic alcohols in excellent enantiomeric excess. In this work, 6Li, 1H and 13 C NMR spectroscopy have been used to study the aggregation of the chiral lithium amide in THF and the influence on the aggregation by the addition of additives, such as 1,8-diazabicyclo-[5.4.0]undec-7-ene (DBU). The activated complex under catalytic deprotonation of cyclohexene oxide, that is, with excess Li-DBU and free DBU, is built from one monomer of the chiral lithium amide, one molecule of epoxide and one additional molecule of DBU. The reaction order (0.97) obtained for the bulk base Li-DBU shows an inverse dependence on the concentration, suggesting a deaggregation of the initial mixed dimer to a monomer-based transition state containing a monomer of the lithium amide.

  • 23.
    Dinér, Peter
    Uppsala University.
    Superacid-Promoted Ionization of Alkanes Without Carbonium Ion Formation: A Density Functional Theory Study2012In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 116, no 40, p. 9979-9984Article in journal (Refereed)
  • 24.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Superacid-Promoted Ionization of Alkanes Without Carbonium Ion Formation: A Density Functional Theory Study2012In: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 116, no 40, p. 9979-9984Article in journal (Refereed)
    Abstract [en]

    The carbonium ion has been suggested to be the intermediate in superacid-promoted reactions (SbF5-HF) such as hydrogen-deuterium exchange and in the electrophilic C-H cleavage into hydrogen and the carbenium ion. In this study, the superacid-promoted C-H cleavage into hydrogen and the carbenium ion was studied using density functional theory (B3LYP and M062X) and ab initio methods (MP2 and CCSD). The calculations suggest that the superacid-promoted C-H cleavage proceeds via a concerted transition state leading to hydrogen (H-2) and the carbenium ion without the formation of the elusive carbonium ion. The reactivity for the superacid promoted C-H cleavage decreases upon going from isobutane (tertiary) > propane (secondary) > isobutane (primary) > propane (primary) > ethane >> methane.

  • 25.
    Dinér, Peter
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Yttrium from Ytterby2016In: Nature Chemistry, ISSN 1755-4330, E-ISSN 1755-4349, Vol. 8, no 2, p. 192-192Article in journal (Refereed)
  • 26.
    Dinér, Peter
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Alao, John P.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Söderlund, Johan
    Sunnerhagen, Per
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Grøtli, Morten
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Preparation of 3-Substituted-1-Isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines as RET Kinase Inhibitors2012In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 55, no 10, p. 4872-4876Article in journal (Refereed)
    Abstract [en]

    A series of 3-substituted-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines have been designed, synthesized, and evaluated as RET protein kinase inhibitors. On the basis of docking results, a small library of pyrazolopyrimidine compounds with an extended hydrophobic side arm was synthesized. The most promising of the compounds (7a) displayed efficient inhibition in vitro and good selectivity when tested on a panel of kinases. Furthermore, 7a inhibited GDNF-induced RET phosphorylation of ERK1/2 in MCF-7 breast cancer cells at concentrations as low as 100 nM.

  • 27.
    Dinér, Peter
    et al.
    University of Gothenburg.
    Alao, John Patrick
    Söderlund, Johan
    Sunnerhagen, Per
    Grøtli, Morten
    Preparation of 3-Substituted-1-Isopropyl-1H-pyrazolo 3,4-d pyrimidin-4-amines as RET Kinase Inhibitors2012In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 55 4872-4876, no 10, p. 4872-4876Article in journal (Refereed)
  • 28.
    Dinér, Peter
    et al.
    Organic Chemistry, Department of Chemistry, Göteborg University.
    Amedjkouh, Mohamed
    Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction: towards syn selectivity in the presence of Lewis bases2006In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 4, no 11, p. 2091-2096Article in journal (Refereed)
    Abstract [en]

    Chiral alpha-aminophosphonates have been synthesized and their performance was evaluated as organocatalysts in the direct asymmetric aldol reaction. High enantioselectivities (up to 99% ee) were achieved for a range of substituted cyclohexanones and benzaldehydes. Several organic bases, such as DBU, DBN, and TMG, were used together with the alpha-aminophosphonates in the aldol reactions and were found to favor syn-selectivity.

  • 29.
    Dinér, Peter
    et al.
    Department of Chemistry, University of Gothenburg.
    Amedjkouh, Mohamed
    Aminophosphonates as organocatalysts in the direct asymmetric aldol reaction towards syn selectivity in the presence of Lewis bases2006In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 4, no 11, p. 2091-2096Article in journal (Refereed)
  • 30.
    Dinér, Peter
    et al.
    University of Gothenburg.
    Andersson, T.
    Kjellén, J.
    Elbing, K.
    Hohmann, S.
    Grotli, M.
    Short cut to 1,2,3-triazole-based p38 MAP kinase inhibitors via [3+2]-cycloaddition chemistry2009In: New Journal of Chemistry, ISSN 1144-0546, E-ISSN 1369-9261, Vol. 331010-1016, no 5, p. 1010-1016Article in journal (Refereed)
  • 31.
    Dinér, Peter
    et al.
    Danish National Research Foundation, Aarhus University.
    Kjaersgaard, Anne
    Lie, Mette Alstrup
    Jørgensen, Karl Anker
    On the origin of the stereoselectivity in organocatalysed reactions with trimethylsilyl-protected Diarylprolinol2008In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, no 1, p. 122-127Article in journal (Refereed)
  • 32.
    Dinér, Peter
    et al.
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Kjaersgaard, Anne
    Lie, Mette Alstrup
    Jørgensen, Karl Anker
    On the origin of the stereoselectivity in organocatalysed reactions with trimethylsilyl-protected diarylprolinol2008In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 14, no 1, p. 122-127Article in journal (Refereed)
    Abstract [en]

    The origin of the enantioselectivity in the TMS-protected (TMS=trimethylsilyl) prolinol-catalysed alpha-heteroatom functionalisation of aldehydes has been investigated by using density functional theory calculations. Eight different reaction paths have been considered which are based on four different conformers of the TMS-protected prolinol-enamine intermediate. Optimisation of the enamine structures gave two intermediates with nearly the same energy. These intermediates both have an E configuration at the C==C bond and the double bond is positioned anti or syn, relative to the 2-substituent in the pyrrolidine ring. For the four intermediates, the chiral TMS-protected-diaryl substituent effectively shields one of the faces of the reacting C==C bond in the enamine intermediate. A number of transition states have been calculated for the enantioselective fluorination by N-fluorobenzenesulfonimide (NFSI) and based on the transition-state energies it has been found that the enantioselectivity depends on the orientation of the C==C bond, being anti or syn, relative to the 2-substituent on the pyrrolidine ring, rather than the approach of the electrophilic fluorine to the face of the reacting carbon atom in the enamine which is less shielded relative to the face with the highest shielding. The calculated enantiomeric excess of 96 % ee (ee=enantiomeric excess) for the fluorination reaction corresponds well with the experimentally found enantiomeric excess-97 % ee. The transition state for the alpha-amination reaction with the same type of intermediate has also been calculated by using diethyl azodicarboxylate as the amination reagent. The implication of the intermediate structures on the stereoselection of alpha-functionalisation of aldehydes is discussed.

  • 33.
    Dinér, Peter
    et al.
    Danish National Research Foundation, Aarhus University.
    Nielsen, Martin
    Bertelsen, Søren
    Niess, Barbara
    Jørgensen, Karl Anker
    Enantioselective hydroxylation of nitroalkenes: an organocatalytic approach2007In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 35, p. 3646-3648Article in journal (Refereed)
  • 34.
    Dinér, Peter
    et al.
    Center for Catalysis, Department of Chemistry, Aarhus University.
    Nielsen, Martin
    Bertelsen, Søren
    Niess, Barbara
    Jørgensen, Karl Anker
    Enantioselective hydroxylation of nitroalkenes: an organocatalytic approach2007In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 35, p. 3646-3648Article in journal (Refereed)
    Abstract [en]

    An easy hydroxylation of aliphatic nitroalkenes in high yields and enantioselectivities is catalysed by bifunctional thiourea-cinchona alkaloids giving access to optically active nitroalcohols and aminoalcohols as final products.

  • 35.
    Dinér, Peter
    et al.
    Danish National Research Foundation, Aarhus University.
    Nielsen, Martin
    Marigo, Mauro
    Jørgensen, Karl Anker
    Enantioselective organocatalytic conjugate addition of N heterocycles to alpha,beta-unsaturated aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, no 12, p. 1983-1987Article in journal (Refereed)
  • 36.
    Dinér, Peter
    et al.
    Center for Catalysis Department of Chemistry, Aarhus University.
    Nielsen, Martin
    Marigo, Mauro
    Jørgensen, Karl Anker
    Enantioselective organocatalytic conjugate addition of N heterocycles to alpha,beta-unsaturated aldehydes2007In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 46, no 12, p. 1983-1987Article in journal (Refereed)
  • 37.
    Dinér, Peter
    et al.
    University of Gothenburg.
    Pettersen, Daniel
    Nilsson Lill, Sten O.
    Ahlberg, Per
    Investigation of site selectivity of the stereoselective deprotonation of cyclohexene oxide using kinetic resolution of isotopic enantiomers in natural abundance2005In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 162665-2671, no 15, p. 2665-2671Article in journal (Refereed)
  • 38.
    Dinér, Peter
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Sadhukhan, Arghya
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Blomkvist, Björn
    KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Chiral Sulfinamides as Highly Enantioselective Organocatalysts2014In: ChemCatChem, ISSN 1867-3880, E-ISSN 1867-3899, Vol. 6, no 11, p. 3063-3066Article in journal (Refereed)
  • 39.
    Dinér, Peter
    et al.
    University of Gothenburg.
    Veide Vilg, Jenny
    Kjellén, Jimmy
    Andersson, Terese
    Hohmann, Stefan
    Tamás, Markus J.
    Grøtli, Morten
    Highly selective, cell-permeable and fast-acting wild-type Hog1 inhibitors as tools for studying cellular function of kinases2009In: Functional Genomics Symposium: Chemical Biology – Molecules to Probe Life, Gothenburg, Sweden, University of Gothenburg , 2009Conference paper (Refereed)
  • 40.
    Dinér, Peter
    et al.
    University of Gothenburg.
    Veide Vilg, Jenny
    Kjellén, Jimmy
    Migdal, Iwona
    Andersson, Terese
    Gebbia, Marinella
    Giaever, Guri
    Nislow, Corey
    Hohmann, Stefan
    Wysocki, Robert
    Tamás, Markus J.
    Grøtli, Morten
    Design, synthesis, and characterization of a highly effective Hog1 inhibitor: a powerful tool for analyzing MAP kinase signaling in yeast2011In: PLoS ONE, ISSN 1932-6203, E-ISSN 1932-6203, Vol. 6, no 5Article in journal (Refereed)
  • 41.
    Dinér, Peter
    et al.
    University of Gothenburg.
    Veide Vilg, Jenny
    Kjellén, Jimmy
    Migdal, Iwona
    Andersson, Terese
    Gebbia, Marinella
    Giaever, Guri
    Nislow, Corey
    Hohmann, Stefan
    Wysocki, Robert
    Tamás, Markus J.
    Grøtli, Morten
    Design, Synthesis, and Characterization of a Highly Effective Hog1 Inhibitor: A Powerful Tool for Analyzing MAP Kinase Signaling in Yeast2011In: PLoS ONE, Vol. 6, no 5, p. e20012-Article in journal (Refereed)
    Abstract [en]

    The Saccharomyces cerevisiaeHigh-Osmolarity Glycerol (HOG) pathway is a conserved mitogen-activated protein kinase (MAPK) signal transduction system that often serves as a model to analyze systems level properties of MAPK signaling. Hog1, the MAPK of the HOG-pathway, can be activated by various environmental cues and it controls transcription, translation, transport, and cell cycle adaptations in response to stress conditions. A powerful means to study signaling in living cells is to use kinase inhibitors; however, no inhibitor targeting wild-type Hog1 exists to date. Herein, we describe the design, synthesis, and biological application of small molecule inhibitors that are cell-permeable, fast-acting, and highly efficient against wild-type Hog1. These compounds are potent inhibitors of Hog1 kinase activity both in vitroand in vivo. Next, we use these novel inhibitors to pinpoint the time of Hog1 action during recovery from G1 checkpoint arrest, providing further evidence for a specific role of Hog1 in regulating cell cycle resumption during arsenite stress. Hence, we describe a novel tool for chemical genetic analysis of MAPK signaling and provide novel insights into Hog1 action.

  • 42. Dinér, Peter
    et al.
    Veide Vilg, Jenny
    Kjellén, Jimmy
    Migdal, Iwona
    Andersson, Therese
    Hohmann, Stefan
    Wysocki, Robert
    Tamás, Markus J.
    Grøtli, Morten
    Design, synthesis and characterization of a highly effective Hog1 inhibitor: a powerful tool for analyzing MAP kinase signalling in yeast2010In: Yeast Genetics and Molecular Biology Meeting, Vancouver, Canada, 2010Conference paper (Refereed)
  • 43. Dinér, Peter
    et al.
    Vilg, J V
    Kjellen, J
    Iwona, M
    Andersson, T
    Hohmann, S
    Wysocki, R
    Tamas, M J
    Grotli, M
    Design, synthesis and characterization of a highly effective Hog1 inhibitor: a powerful tool for analyzing MAP kinase signaling in yeast2010In: Special Issue: Abstracts of the 35th FEBS Congress, Gothenburg, Sweden, 26 June - 1 July 2010, Wiley-Blackwell, 2010, Vol. 277Conference paper (Other academic)
  • 44.
    Dyrager, C.
    et al.
    University of Gothenburg.
    Börjesson, K.
    Chalmers University of Technology.
    Dinér, P.
    University of Gothenburg.
    Elf, A.
    University of Gothenburg.
    Albinsson, B.
    Chalmers University of Technology.
    Wilhelmsson, L. M.
    Chalmers University of Technology.
    Grotli, M.
    University of Gothenburg.
    Synthesis and Photophysical Characterisation of Fluorescent 8-(1H-1,2,3-Triazol-4-yl)adenosine Derivatives2009In: European Journal of Organic Chemistry, no 10, p. 1515-1521Article in journal (Refereed)
    Abstract [en]

    A series of 8-(1H-1,2,3-triazol-4-yl)-substituted adenosine derivatives have been synthesised by using Sonogashira cross-coupling and click chemistry. The use of click chemistry enables an easy access to different substituents in the 4-position of the triazole ring. The modified nucleosides show high absorptivities due to a single strongly allowed electronic transition and, for some of the derivatives, high quantum yields in organic as well as in water solution making them promising as fluorescent probes in nucleic acid contexts. Furthermore, the different substituents of the 1,2,3-triazole makes the wavelength of emission tunable without changing the absorption properties substantially. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  • 45. Dyrager, Christine
    et al.
    Börjesson, Karl
    Dinér, Peter
    University of Gothenburg.
    Elf, A.
    Albinsson, Bo
    Wilhelmsson, Marcus
    Grøtli, Morten
    Synthesis and Photophysical Characterisation of Fluorescent 8-(1H-1,2,3-Triazol-4-yl)adenosine Derivatives2009In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 10, p. 1515-1521Article in journal (Refereed)
  • 46.
    Dyrager, Christine
    et al.
    University of Gothenburg.
    Nilsson Möllers, Linda
    University of Gothenburg.
    Kjäll, Linda Karlsson
    University of Gothenburg.
    Alao, John Patrick
    University of Gothenburg.
    Diner, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Wallner, Fredrik
    University of Gothenburg.
    Sunnerhagen, Per
    University of Gothenburg.
    Grøtli, Morten
    University of Gothenburg.
    Design, Synthesis and Biological Evaluation of Chromone-based p38 MAP Kinase Inhibitors2011In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 54, no 20, p. 7427-7431Article in journal (Refereed)
    Abstract [en]

    A series of 3-(4-fluorophenyl)-2-(4-pyridyl)-chromone derivs. were synthesized and evaluated as p38 MAP kinase inhibitors. Introduction of an amino group in the 2-position of the pyridyl moiety gave p38 inhibitors with IC50 values in the low nanomolar range (e.g. 8a; IC50 = 17 nm). Addnl., the inhibitors (8a and 8e) demonstrate an excellent selectivity profile towards the p38 kinase among other kinases, as well as inhibition (8e) of p38 signaling in human breast cancer cells. [on SciFinder(R)]

  • 47. Dyrager, Christine
    et al.
    Nilsson Möllers, Linda
    Kjäll, Linda Karlsson
    Alao, John Patrick
    Dinér, Peter
    University of Gothenburg.
    Wallner, Fredrik
    Sunnerhagen, Per
    Grøtli, Morten
    Möllers, Linda N
    Design, synthesis, and biological evaluation of chromone-based p38 MAP kinase inhibitors2011In: Journal of Medicinal Chemistry, ISSN 0022-2623, E-ISSN 1520-4804, Vol. 54Article in journal (Refereed)
  • 48. Díaz-Álvarez, Alba E.
    et al.
    Mesas Sanchez, Laura
    Dinér, Peter
    Uppsala University.
    Non-Enzymatic Dynamic Kinetic Resolution of Secondary Aryl Alcohols: Planar Chiral Ferrocene and Ruthenium Catalysts in Cooperation2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52502-504, no 2, p. 502-504Article in journal (Refereed)
  • 49.
    Díaz-Álvarez, Alba E.
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Mesas Sanchez, Laura
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Dinér, Peter
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
    Non-Enzymatic Dynamic Kinetic Resolution of Secondary Aryl Alcohols: Planar Chiral Ferrocene and Ruthenium Catalysts in Cooperation2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 2, p. 502-504Article in journal (Refereed)
  • 50. Díaz-Álvarez, Alba E.
    et al.
    Mesas-Sánchez, Laura
    Dinér, Peter
    Uppsala University.
    Nichtenzymatische dynamische kinetische Racematspaltung sekundärer Arylalkohole: planar-chirale Ferrocen- und Rutheniumkatalysatoren im Zusammenspiel2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 125, no 2, p. 522-524Article in journal (Refereed)
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