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

被引:105
作者
Choi, Taylor A. [1 ,2 ]
Czerwonka, Regina [1 ]
Forke, Ronny [1 ]
Jaeger, Anne [1 ]
Knoell, Jan [1 ]
Krahl, Micha P. [1 ]
Krause, Tilo [1 ]
Reddy, Kethiri R. [1 ]
Franzblau, Scott G. [2 ]
Knoelker, Hans-Joachim [1 ]
机构
[1] Tech Univ Dresden, Dept Chem, D-01069 Dresden, Germany
[2] Univ Illinois, Coll Pharm, Inst TB Res, Chicago, IL 60612 USA
关键词
D O I
10.1007/s00044-007-9073-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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.
引用
收藏
页码:374 / 385
页数:12
相关论文
共 48 条
[1]   Novel routes to pyrroles, indoles and carbazoles -: Applications in natural product synthesis [J].
Agarwal, S ;
Cämmerer, S ;
Filali, S ;
Fröhner, W ;
Knöll, J ;
Krahl, MP ;
Reddy, KR ;
Knölker, HJ .
CURRENT ORGANIC CHEMISTRY, 2005, 9 (15) :1601-1614
[2]  
[Anonymous], SELECTED METHODS S 1
[3]  
[Anonymous], CHEM BIOL ACTIVITY S
[4]  
BHATTACHARYYA P, 1984, INDIAN J CHEM B, V23, P49
[5]  
CHAKRABORTY D P, 1975, Transactions of the Bose Research Institute (Calcutta), V38, P1
[6]  
Chakraborty D P, 1991, Fortschr Chem Org Naturst, V57, P71
[7]  
Chakraborty D.P., 1993, The Alkaloids, V44, P257
[8]  
CHAKRABORTY DP, 1966, TETRAHEDRON LETT, P661
[9]  
Choi TA, 2006, CHEMMEDCHEM, V1, P812, DOI 10.1002/cmdc.20060002
[10]   Microplate Alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium [J].
Collins, LA ;
Franzblau, SG .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 41 (05) :1004-1009