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Sökning: db:Swepub > Södertörns högskola > Bergman Jan

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1.
  • Bergander, L, et al. (författare)
  • Characterization of in vitro metabolites of the aryl hydrocarbon receptor ligand 6-formylindolo[3,2-b] carbazole by liquid chromatography-mass spectrometry and NMR.
  • 2003
  • Ingår i: Drug Metabolism And Disposition. - : American Society for Pharmacology & Experimental Therapeutics (ASPET). - 0090-9556 .- 1521-009X. ; 31:2, s. 233-241
  • Tidskriftsartikel (refereegranskat)abstract
    • The tryptophan photoproduct 6-formylindolo[3,2-b] carbazole (FICZ) exhibits the highest aryl hydrocarbon receptor (AhR) binding affinity reported so far. In different cells, in vitro, both extracts of UV-irradiated tryptophan and the synthesized pure compound FICZ induce a rapid and transient expression of AhR-regulated genes. The transient induction suggests that the biotransformation gene battery induced by AhR activation takes part in a metabolic degradation of the ligand, whereby a low steady-state level is regained. The down-regulation of AhR-regulated gene expression was previously shown to be dependent on cytochrome P450 1A1 (CYP1A1). Metabolism of FICZ generates five major metabolites, which appeared as three peaks (M1-M3) in the high performance liquid chromatography. The aim of the present study was to use rat liver S9 from Aroclor-pretreated rats to produce large enough quantities of FICZ metabolites for structure characterization and to determine their product precursor relationship. NMR analysis of large combined fractions of the metabolites indicated that M3 and M2 contained 2 isomers, respectively. By means of liquid chromatography-mass spectrometry (negative ion electrospray mode) and NMR spectroscopy (by H-1-NMR, correlation spectroscopy, and nuclear Overhauser effect spectroscopy techniques) five metabolites of FICZ were identified, and their structures were elucidated. The molecular weights of the two M3 isomers were 300 and both M2 and M1 compounds demonstrated molecular weights of 316, corresponding to addition of one (M3) and of two oxygen (M2 and M1), respectively. The structures were assigned as 2- and 8-hydroxy (M3), 2,10- and 4,8-dihydroxy (M2) and 2,8-dihydroxy derivatives of indolo[3,2-b] carbazole-6-carboxaldehyde (6-formylindolo[ 3,2-b] carbazole).
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3.
  • Bergman, Jan, et al. (författare)
  • Acid-induced dimerization of 3-(1H-indol-3-yl)maleimides. Formation of cyclopentindole derivatives
  • 2000
  • Ingår i: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1. - : Royal Society of Chemistry (RSC). - 1470-4358 .- 1364-5463 .- 1472-7781. ; :16, s. 2615-2621
  • Tidskriftsartikel (refereegranskat)abstract
    • Acid-induced dimerizations of 3-substituted maleimides have been investigated, leading to e.g. the cyclopentindole 9 and the deeply coloured spiro compounds 24 and 25 in good yields. 3-(1H-Indol-3-yl)maleimide 6b readily gave the cycloaddition products 13-15 on treatment with appropriate dienophiles. In addition, several related 3,3-di-(1H-indol-3-yl)succinimides have been prepared and studied.
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4.
  • Bergman, Jan, et al. (författare)
  • Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A
  • 2000
  • Ingår i: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1. - : Royal Society of Chemistry (RSC). - 1470-4358 .- 1364-5463 .- 1472-7781. ; :16, s. 2609-2614
  • Tidskriftsartikel (refereegranskat)abstract
    • The bisindolesuccinic acid methyl ester 10 was obtained by an iodine-promoted coupling of the dianion 9. The diester was converted to the N-benzylimide 12, which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]carbazole 15. The diester 10 could be directly transformed to the known indolocarbazole diester 27 via acid-induced intramolecular cyclization in TFA. The same methodology gave arcyriaflavin A 4 from the succinimide 18b.
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5.
  • Bergman, Jan, et al. (författare)
  • Indolocarbazoles
  • 2001
  • Ingår i: ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 80. - 0065-2725 .- 1557-8429. ; 80, s. 1-71
  • Forskningsöversikt (övrigt vetenskapligt/konstnärligt)
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6.
  • Bergman, Jan, et al. (författare)
  • Reactions of 1,2-bis(1H-indol-2-yl)ethane : Formation of indolo[2,3-c]carbazole and cyclohept[1,2-b : 5,4-b ']bisindole derivatives
  • 2000
  • Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 56:13, s. 1911-1916
  • Tidskriftsartikel (refereegranskat)abstract
    • 1,2-Bis(1H-indol-2-yl)ethane (9) has been prepared and converted into indolo[2,3-c]carbazole (8) using palladium acetate in refluxing acetic acid. Reaction of 9 with CoF3 in hot TFA led to isolation of cyclohept[1,2-b:5,4-b']bisindole derivatives 11 and 12, which could be elaborated into further derivatives. Treatment of 9 with orthoesters, aldehydes and ketones under acidic conditions afforded additional bisindoles containing a seven-membered ring.
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8.
  • Bergman, Jan, et al. (författare)
  • Studies of the reactions between indole-2,3-diones (isatins) and 2-aminobenzylamine
  • 2003
  • Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 59:7, s. 1033-1048
  • Tidskriftsartikel (refereegranskat)abstract
    • Reflux of equimolecular amounts 2-aminobenzylamine and isatins in acetic acid produced indolo[3,2-c]quinolin-6-ones in good yields. A proposed mechanism involving initial formation of a spiro compound is given. This isolable intermediate subsequently rearranges via a sequential isocyanate ring opening and a cyclisation process to a urea derivative which finally cyclized to the indolo[3,2-c]quinolin-6-ones. The urea derivative could be prepared separately and cyclized selectively to indolo[3,2-c]quinolin-6-one. Reaction of N-acetylisatin with 2-aminobenzylamine at room temperature yielded the 1,4-benzodiazepinone 3-(2-acetamidophenyl)-1,5-dihydro-1,4-benzodiazepin-2one whereas its isomer 2(2-acetamidophenyl)-4,5-dihydro-1,4-benzodiazepin-3-one was obtained from 2-(2-acetylaminophenyl)-N-(2-aminobenzyl)-2-oxoacetamide in acetic acid at room temperature. The previously unknown linear isomer of indolo[3,2-c]quinolin-6-one, i.e. indolo[2,3-blquinolin-11-one, has been prepared by thermal (260degreesC) cyclization of methyl 2-phenylamino indole-3-carboxylate, which in turn was prepared in two steps from methyl indole-3-carboxyl ate. (C) 2003 Elsevier Science Ltd. All rights reserved.
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10.
  • Bergman, Jan, et al. (författare)
  • Synthesis of indolocarbazole quinones; potent aryl hydrocarbon receptor ligands
  • 2002
  • Ingår i: Tetrahedron. - 0040-4020 .- 1464-5416. ; 58:7, s. 1443-1452
  • Tidskriftsartikel (refereegranskat)abstract
    • Syntheses of indolo[2,3-b]carbazole-6,12-dione and the isomeric indolo[3,2-b]carbazole-6,12-dione, an extremely efficient inducer of the aryl hydrocarbon (Ah) receptor are described. Initial oxidation of the parent indolo[3,2-b]carbazole followed by several different ring-closing strategies produced the latter compound. Entries into syntheses of unsymmetrical 6,12-disubstituted indolo[2,3-b]carbazoles are also described.
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