title: Anti-tuberculosis activity and structure-activity relationships of oxygenated tricyclic carbazole alkaloids and synthetic derivatives.
abstract: A series of 49 oxygenated tricyclic carbazole derivatives has been tested for inhibition of the growth of Mycobacterium tuberculosis and a mammalian cell line (vero cells). From this series, twelve carbazoles showed a significant anti-TB activity. The four most active compounds were the naturally occurring carbazole alkaloids clauszoline-M (45), murrayaline-C (41), carbalexin-C (27), and the synthetic carbazole derivative 22 with MIC90values ranging from 1.5 to 3.7μM. The active compounds were virtually nontoxic for the mammalian cell line in the concentration range up to 50μM.
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: Carsten
authors.initials: C
authors.lastname: Börger
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: Christian
authors.initials: C
authors.lastname: Brütting
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: Konstanze K
authors.initials: KK
authors.lastname: Julich-Gruner
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: Ronny
authors.initials: R
authors.lastname: Hesse
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: V Pavan
authors.initials: VP
authors.lastname: Kumar
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: Sebastian K
authors.initials: SK
authors.lastname: Kutz
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: Marika
authors.initials: M
authors.lastname: Rönnefahrt
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany.
authors.forename: Claudia
authors.initials: C
authors.lastname: Thomas
authors.affiliation: Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., MC 964, Chicago, IL 60612-7231, USA.
authors.forename: Baojie
authors.initials: B
authors.lastname: Wan
authors.affiliation: Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., MC 964, Chicago, IL 60612-7231, USA.
authors.forename: Scott G
authors.initials: SG
authors.lastname: Franzblau
authors.affiliation: Department Chemie, Technische Universität Dresden, Bergstraße 66, 01069 Dresden, Germany. Electronic address: hans-joachim.knoelker@tu.dresden.de.
authors.forename: Hans-Joachim
authors.initials: HJ
authors.lastname: Knölker
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D002522:Chlorocebus aethiops; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D013329:Structure-Activity Relationship; D014709:Vero Cells
chemical_list: D000470:Alkaloids; D000995:Antitubercular Agents; D002227:Carbazoles
keywords: Alkaloids; Anti-TB activity; Carbazoles; Natural products; Tuberculosis