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1H-Indole

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Clas Sonesson – One of the best experts on this subject based on the ideXlab platform.

Cecilia Mattsson – One of the best experts on this subject based on the ideXlab platform.

  • Structure–activity relationship of 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indole analogues as 5-HT6 receptor agonists
    European Journal of Medicinal Chemistry, 2013
    Co-Authors: Cecilia Mattsson, Peder Svensson, Henning Boettcher, Clas Sonesson
    Abstract:

    Abstract To further investigate the structure–activity relationship (SAR) of the 5-hydroxytryptamine type 6 (5-HT6) receptor agonist 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indole (EMD386088, 6), a series of 2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indoles were synthesized, and in vitro affinity to, and functional activity at 5-HT6 receptors was tested. We focused on substituents made at the indole N1-, 2- and 5-positions and these were found to not only influence the affinity at 5-HT6 receptors but also the intrinsic activity leading to antagonists, partial agonists and full agonists. In order for a compound to demonstrate potent 5-HT6 receptor agonist properties, the indole N1 should be unsubstituted, an alkyl group such as 2-methyl is needed and finally halogen substituents in the indole 5-position (fluoro, chloro or, bromo) were essential requirements. However, the introduction of a benzenesulfonyl group at N1-position switched the full agonist 6 to be a 5-HT6 receptor antagonist (30). A few compounds within the 2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indoles were also screened for off-targets and generally they displayed low affinity for other 5-HT subtypes and serotonin transporter protein (SERT).

  • 2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indoles as novel 5-HT6 receptor agonists.
    Bioorganic & medicinal chemistry letters, 2005
    Co-Authors: Cecilia Mattsson, Clas Sonesson, Anna Sandahl, Hartmut Greiner, Michael Gassen, Jörg Plaschke, Joachim Leibrock, Henning Böttcher
    Abstract:

    Abstract A series of 2-alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indoles were synthesized and evaluated for their 5-HT6 activity. The most potent agonist in this series was 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indole with an IC50 = 7.4 nM in 3H-LSD binding and an EC50 = 1.0 nM in a functional assay measuring production of cyclic AMP.

Henning Böttcher – One of the best experts on this subject based on the ideXlab platform.

  • 2-Alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indoles as novel 5-HT6 receptor agonists.
    Bioorganic & medicinal chemistry letters, 2005
    Co-Authors: Cecilia Mattsson, Clas Sonesson, Anna Sandahl, Hartmut Greiner, Michael Gassen, Jörg Plaschke, Joachim Leibrock, Henning Böttcher
    Abstract:

    Abstract A series of 2-alkyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indoles were synthesized and evaluated for their 5-HT6 activity. The most potent agonist in this series was 5-chloro-2-methyl-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-Indole with an IC50 = 7.4 nM in 3H-LSD binding and an EC50 = 1.0 nM in a functional assay measuring production of cyclic AMP.

Antonio Espinosa – One of the best experts on this subject based on the ideXlab platform.

  • Design, syntheses, biological evaluation, and docking studies of 2-substituted 5-methylsulfonyl-1-phenyl-1H-Indoles: potent and selective in vitro cyclooxygenase-2 inhibitors.
    ChemMedChem, 2007
    Co-Authors: Olga Cruz-lopez, Joaquín M. Campos, Miguel A. Gallo, Juan J. Diaz-mochon, Antonio Entrena, Maria Teresa Nunez, Luis Labeaga, Aurelio Orjales, Antonio Espinosa
    Abstract:

    Four series of 5-methylsulfonyl-1-phenyl-1H-Indole-2-carboxylic acid alkyl esters (family A), -2-carbonitriles (family B), -2-carboxamides (family C), and 2-benzoyl-5-methylsulfonyl-1-phenyl-1H-Indoles (family D) were prepared and evaluated for their ability to inhibit purified cyclooxygenase-2 (COX-2) and cyclooxygenase-1 (COX-1). Family D compounds have the best COX-1/COX-2 inhibition ratios and potencies. According to docking studies, these molecules appear to bind the COX-2 binding site differently than indomethacin, with the insertion of the substituent at the 2-position in the hydrophobic pocket of the enzyme and the 1-position phenyl ring in the trifluoromethyl zone. Among the group of compounds evaluated, 2-(4-chlorobenzoyl)-1-(4-chlorophenyl)-5-methylsulfonyl-1H-Indole and 2-(4-chlorophenyl)-5-methylsulfonyl-1-(4-trifluoromethylphenyl)-1H-Indole emerged as the most potent (respective IC 50 values: 46 and 43 nM), and selective (respective selectivity indexes: >2163 and >2331) COX-2 inhibitors.

  • 1H and 13C NMR studies of 2-functionalized 5-(methylsulfonyl)-1-phenyl-1H-Indoles.
    Magnetic resonance in chemistry : MRC, 2007
    Co-Authors: Olga Cruz-lopez, Miguel A. Gallo, Antonio Espinosa, Joaquín M. Campos
    Abstract:

    The 1H and 13C NMR resonances of thirty 2-functionalized 5-(methylsulfonyl)-1-phenyl-1H-Indoles were assigned completely and unequivocally using the concerted application of one- and two-dimensional experiments (DEPT, gs-HMQC and gs-HMBC). Finally, the influence of the 2-substituent of 5-(methylsufonyl)-1-phenyl-1H-Indoles on the carbon atoms of the indole moiety was estimated. Copyright © 2006 John Wiley & Sons, Ltd.

Bijoy Kundu – One of the best experts on this subject based on the ideXlab platform.

  • new route to the synthesis of the isocryptolepine alkaloid and its related skeletons using a modified pictet spengler reaction
    European Journal of Organic Chemistry, 2009
    Co-Authors: Piyush K. Agarwal, Devesh Sawant, Sunil Sharma, Bijoy Kundu
    Abstract:

    A new route to the synthesis of the isocryptolepine alkaloid with antimalarial activity using a modified Pictet–Spengler reaction has been devised. The strategy was then used to generate libraries based on three structural variants of the alkaloid. Compounds based on these three variants in general were accessed in three steps through a modified Pictet–Spengler cyclization reaction as the key step. The C-2-, C-3-, or N-1-linked (aminoaryl)indoles (8, 12, 13) required for cyclization were obtained by treating the corresponding indoles with o-halonitrobenzene using either nucleophilic replacement or Pd-based chemistry (Heck/Suzuki reaction) followed by reduction of the nitroaryl functionality. The substrates 8, 12, and 13 were then subjected to the Pictet–Spengler reaction to furnish polycyclic structures, indolo-quinolines 4 and 19 and indolo-quinoxalines 20 with three-point diversity in high yields and purities. One of the indolo-quinolines 4a after treatment with CH3I furnished the isocryptolepine alkaloid in excellent yield. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  • New Route to the Synthesis of the Isocryptolepine Alkaloid and Its Related Skeletons Using a Modified Pictet–Spengler Reaction†
    European Journal of Organic Chemistry, 2009
    Co-Authors: Piyush K. Agarwal, Devesh Sawant, Sunil Sharma, Bijoy Kundu
    Abstract:

    A new route to the synthesis of the isocryptolepine alkaloid with antimalarial activity using a modified Pictet–Spengler reaction has been devised. The strategy was then used to generate libraries based on three structural variants of the alkaloid. Compounds based on these three variants in general were accessed in three steps through a modified Pictet–Spengler cyclization reaction as the key step. The C-2-, C-3-, or N-1-linked (aminoaryl)indoles (8, 12, 13) required for cyclization were obtained by treating the corresponding indoles with o-halonitrobenzene using either nucleophilic replacement or Pd-based chemistry (Heck/Suzuki reaction) followed by reduction of the nitroaryl functionality. The substrates 8, 12, and 13 were then subjected to the Pictet–Spengler reaction to furnish polycyclic structures, indolo-quinolines 4 and 19 and indolo-quinoxalines 20 with three-point diversity in high yields and purities. One of the indolo-quinolines 4a after treatment with CH3I furnished the isocryptolepine alkaloid in excellent yield. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)