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Transition metals in organic synthesis - Part 83#: Synthesis and pharmacological potential of carbazoles

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Abstract

A series of carbazole derivatives with promising pharmacological properties has been prepared using either an iron-mediated or a palladium-catalyzed synthetic approach. The carbazole alkaloids carbazoquinocin C, carbazomadurin A and B, epocarbazolin A and B, neocarazostatin B, and carquinostatin A are antioxidants acting as free-radical scavengers. Thus, they represent potential lead compounds for the development of novel drugs against diseases initiated by oxygen-derived free radicals. Initiated by the first naturally occurring carbazole alkaloids with antituberculosis (anti-TB) activity, clausine K and micromeline, a study on the structure–activity relationships for anti-TB-active carbazole derivatives has been carried out. The 6-oxygenated carbazoles glycozoline and glycozolinine show antibiotic activity towards several microorganisms. The 7-oxygenated carbazole siamenol exhibits anti-HIV activity.

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Acknowledgement

We are grateful to the European Funds for Regional Development and the State of Saxony (EFRE project 4212/06-08) for financial support of our research. We would also like to thank JADO Technologies, Dresden, for their support.

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Authors and Affiliations

  1. Department Chemie, Technische Universität Dresden, Bergstrasse 66, 01069, Dresden, Germany

    Taylor A. Choi, Regina Czerwonka, Ronny Forke, Anne Jäger, Jan Knöll, Micha P. Krahl, Tilo Krause, Kethiri R. Reddy & Hans-Joachim Knölker

  2. Institute for Tuberculosis Research, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood St., MC 964, Chicago, IL, 60612-7231, USA

    Taylor A. Choi & Scott G. Franzblau

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  1. Taylor A. Choi
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  2. Regina Czerwonka
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  10. Hans-Joachim Knölker
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Correspondence to Hans-Joachim Knölker.

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Choi, T.A., Czerwonka, R., Forke, R. et al. Transition metals in organic synthesis - Part 83#: Synthesis and pharmacological potential of carbazoles. Med Chem Res 17, 374–385 (2008). https://doi.org/10.1007/s00044-007-9073-0

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  • DOI: https://doi.org/10.1007/s00044-007-9073-0

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