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  • 1. Andersson, Maria
    et al.
    Janosik, Tomasz
    Shirani, Hamid
    Slätt, Johnny
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Fischer, Andreas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Inorganic Chemistry.
    Beck, Olof
    Synthesis and bioanalytical evaluation of morphine-3-O-sulfate and morphine-6-O-sulfate in human urine and plasma using LC-MS/MS2012In: Journal of Separation Science, ISSN 1615-9306, E-ISSN 1615-9314, Vol. 35, no 3, p. 367-375Article in journal (Refereed)
    Abstract [en]

    The aim of this work was to synthesize morphine-3-O-sulfate and morphine-6-O-sulfate for use as reference substances, and to determine the sulfate conjugates as possible heroin and morphine metabolites in plasma and urine by a validated LC-MS/MS method. Morphine-6-O-sulfate and morphine-3-O-sulfate were prepared as dihydrates from morphine hydrochloride, in overall yields of 41 and 39% with product purities of >99.5% and >98%, respectively. For bioanalysis, the chromatographic system consisted of a reversed-phase column and gradient elution. The tandem mass spectrometer was operated in the positive electrospray mode using selected reaction monitoring, of transition m/z 366.15 to 286.40. The measuring range was 5500?ng/mL for morphine-3-O-sulfate and 4.5454?ng/mL for morphine-6-O-sulfate in plasma. In urine, the measuring range was 505000?ng/mL for morphine-3-O-sulfate and 45.44544?ng/mL for morphine-6-O-sulfate. The intra-assay and total imprecision (coefficient of variation) was below 11% for both analytes in urine and plasma. Quantifiable levels of morphine-3-O-sulfate in authentic urine and plasma samples were found. Only one authentic urine sample contained a detectable level of morphine-6-O-sulfate, while no detectable morphine-6-O-sulfate was found in plasma samples.

  • 2.
    Hasimbegovic, Vedran
    et al.
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    Slätt, Johnny
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    Bergman, Jan
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    Janosik, Tomasz
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    The synthesis of some 3-acylindoles revisited2007In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, E-ISSN 1943-5193, Vol. 44, no 5, p. 1213-1217Article in journal (Refereed)
    Abstract [en]

    A study probing the scope of acylation of indoles with dicarboxylic acids in acetic anhydride has beenperformed, resulting in products incorporating 3-acylindole- or 1-acylindole motifs depending on thechoice of the acid reactant. Synthetically useful results were only obtained from reactions involvingmalonic acid or Meldrum’s acid. Correlations to previous studies have also been made and discussed.

  • 3.
    Hellberg, Jonas
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Remonen, Tommi
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Allared, Fredrik
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Slätt, Johnny
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Svensson, Mats
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Synthesis of 2,3-dihydrothieno[2,3-b]-1,4-dithiine, 2,3-dihydrothieno[3,2-b]-1,4-oxathiine, 2,3-dihydrothieno[2,3-b]-1,4-oxathiine and their transformation into corresponding end-capped oligomers.2003In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 14, p. 2199-2205Article in journal (Refereed)
    Abstract [en]

    Three new heterocyclic parent compds., 2,3-dihydrothieno[2,3-b][1,4]dithiine, 2,3-dihydrothieno[3,2-b][1,4]oxathiine, and 2,3-dihydrothieno[2,3-b][1,4]oxathiine, have been synthesized by acid-catalyzed transformations starting from 3-methoxythiophene. Two of the new compds. have been transformed to the corresponding end-capped dimeric, trimeric and tetrameric oligothiophenes. These oligomers show very stable cationic and dicationic states as judged by cyclic voltammetry, and their UV-Vis spectra are considerably red-shifted compared to previously synthesized end-capped oligomers. [on SciFinder(R)]

  • 4.
    Johnson, Ann-Louise
    et al.
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Slätt, Johnny
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Janosik, Tomasz
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Bergman, Jan
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Stereoselective synthesis and isomerization of the indole alkaloid murrayacarine2006In: Heterocycles, ISSN 0385-5414, E-ISSN 1881-0942, Vol. 68, no 10, p. 2165-2170Article in journal (Refereed)
    Abstract [en]

    A short and efficient stereoselective synthesis of the indole alkaloid murrayacarine is described, including studies on its acid-induced isomerization.

  • 5.
    Remonen, Tommi
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Hellberg, Jonas
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Slatt, Johnny
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Ethylenedithio end-capped oligothiophenes (bEDTnT); dimer, trimer and tetramer.1999In: Synthetic metals, ISSN 0379-6779, E-ISSN 1879-3290, Vol. 101, no 1-3, p. 107-108Article in journal (Refereed)
    Abstract [en]

    Two new ethylenedithio substituted thiophenes (I; R = H, Br) have been synthesized. Starting from I (R = Br), oligomers II (n = 0, 1, 2) were synthesized. Their cyclic voltammetric behavior and electronic structure (by UV-Vis) have been recorded. Low oxidn. potentials and small differences between first and second oxidn. potential were found. In the UV-Vis spectra large red shifts compared to other end-capped oligomers were obsd. [on SciFinder(R)]

  • 6.
    Slätt, Johnny
    et al.
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park.
    Bergman, Jan.
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park.
    Oxygenation of 2,3-dihydroindoles.2002In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 58, no 45, p. 9187-9191Article in journal (Refereed)
    Abstract [en]

    Indolines (2,3-dihydroindoles) and isatogens (3-oxo-3H-indole 1-oxides) have been prepd. in an efficient route starting from indoles substituted in position 2. Redn. of the 2-substituted indoles was performed with tin and hydrochloric acid to give racemic indolines, which were converted to isatogens by 3-chloroperoxybenzoic acid (m-CPBA). [on SciFinder(R)]

  • 7.
    Slätt, Johnny
    et al.
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Janosik, Tomasz
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Wahlstroem, Niklas
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Bergman, Jan.
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Synthetic applications of 3-(cyanoacetyl)indoles and related compounds2005In: Journal of Heterocyclic Chemistry, ISSN 0022-152X, E-ISSN 1943-5193, Vol. 42, no 1, p. 141-145Article in journal (Refereed)
    Abstract [en]

    Various synthetic applications of 3-(cyanoacetyl)indoles, as well as syntheses of some related indoles, have been investigated. Di-Et 2-(1H-indol-3-yl)-2-oxoethylphosphonate and a Me deriv. thereof have been prepd. in one step from indole. Moreover, it was demonstrated that 3-(cyanoacetyl)indoles are useful starting materials for the prepn. of for example 3-(1H-indol-3-yl)-3-oxopropanamides, 3-heteroarylindoles or 3-heteroaroylindoles.

  • 8.
    Slätt, Johnny
    et al.
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Romero, Ivan
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Bergman, Jan
    Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park,.
    Cyanoacetylation of indoles, pyrroles and aromatic amines with the combination cyanoacetic acid and acetic anhydride2004In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 16, p. 2760-2765Article in journal (Refereed)
    Abstract [en]

    Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivs. For example, the cyanoacetylation of 1H-indole using acetic anhydride/cyanoacetic acid gave β-oxo-1H-indole-3-propanenitrile. The same reaction using 6-amino-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (I) gave 6-amino-1,2,3,4-tetrahydro-1,3-dimethyl-β,2,4-trioxo-5-pyrimidinepropanenitrile (II).

  • 9.
    Wahlström, Niklas
    et al.
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    Slätt, Johnny
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    Stensland, Birgitta
    Early Development, AstraZeneca R&D, Södertälje, Sweden.
    Ertan, Anne
    Early Development, AstraZeneca R&D, Södertälje, Sweden.
    Bergman, Jan
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    Janosik, Tomasz
    Unit for Organic Chemistry, Department of Biosciences and Nutrition, Karolinska Institute, Novum Research Park.
    Synthetic Applications of Cyanoacetylated Bisindoles: Synthesis of Novel Cycloheptadiindoles, Indolocarbazoles, and Related Aza Analogues.2007In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 72, no 15, p. 5886-5889Article in journal (Refereed)
    Abstract [en]

    (Chemical Equation Presented) Cyclization reactions involving cyanoacetylated bisindoles have been studied, providing access to various novel cyclohepta[2,1-b:3,4-b′]diindole derivatives as well as some related fused pentacyclic systems. Treatment of 3-cyanoacetyl-2,3′-diindolylmethane with methanesulfonic acid gave 6-(cyanomethyl)indolo[3,2-b]carbazole in a good yield.

  • 10.
    Wihlborg, Anna-Karin
    et al.
    Department of Cardiology, Lund University, Lund, Sweden.
    Slätt, Johnny
    Organic Chemistry, Novum, Karolinska Institute, Stockholm, Sweden.
    Sun, Xiangyang
    Clinical Pharmacology, Gothenburg University, Gothenburg, Sweden.
    Zhao, Xiao-He
    Clinical Pharmacology, Gothenburg University, Gothenburg, Sweden.
    Malmsjö, Malin
    Clinical Pharmacology, Gothenburg University, Gothenburg, Sweden.
    Bergman, Jan
    Hedner, Thomas
    Clinical Pharmacology, Gothenburg University, Gothenburg, Sweden.
    Erlinge, David
    Department of Cardiology, Lund University, Lund, Sweden.
    2,4'-Nitrophenylisatogen potentiates P2X1 receptor mediated vascular contraction and blood pressure elevation.2003In: Drug development research (Print), ISSN 0272-4391, E-ISSN 1098-2299, Vol. 59, no 1, p. 82-87Article in journal (Refereed)
    Abstract [en]

    The objective of this research was to examine the effects of chem. compds. with possible P2 receptor modulating effects and to characterize the potentiating effects of 2,4'-nitrophenylisatogen (NPI) on P2X1 receptors in vitro and in vivo. Chem. compds. were tested in an in vitro pharmacol. assay using vascular segments from the rat mesenteric artery stimulated by P2 receptor-specific agonists. Contractions were expressed as a percentage of 60 mM K+-induced contractions. Blood pressure was evaluated in pithed rats. NPI (30 ΌM) added 15 min before addn. of the P2X1 receptor-specific agonist αβ-MeATP increased the max. vasoconstriction from 23% to 49% (an increase of 113%). Furthermore, NPI prevented the desensitization of repeated αβ-MeATP contractions. Related compds. were examd., and 2-(3-methoxy-phenyl)-1-oxy-indol-3-one (MPI) had similar effects as NPI, but several others lacked effect. NPI had no effect on ADPβS (P2Y1) or acetylcholine-mediated vasodilatation, nor on UTP (P2Y2/4), UDP (P2Y6), or noradrenaline-mediated contractions. In pithed rats, the blood pressure response to 50 nmol/kg-infusion of αβ-MeATP was increased from 50 to 63 mmHg, but had no effect on basal blood pressure or on the cardiovascular response to preganglionic nerve stimulation. In conclusion, NPI and MPI potentiates P2X1 receptor vascular contractions in vitro and (NPI) blood pressure effects in vivo. It is possible that the effect is mediated by an inhibition of P2X1 receptor desensitization. [on SciFinder(R)]

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