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          Institute: MPI für Kohlenforschung     Collection: Publikationen MPI für Kohlenforschung     Display Documents



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ID: 19908.0, MPI für Kohlenforschung / Publikationen MPI für Kohlenforschung
Efficient relay syntheses and assessment of the DNA-cleaving properties of the pyrrole alkaloid derivatives permethyl storniamide A, lycogalic acid A dimethyl ester, and the halitulin core
Authors:Fürstner, A.; Krause, H.; Thiel, O. R.
Language:English
Date of Publication (YYYY-MM-DD):2002-08-05
Title of Journal:Tetrahedron
Journal Abbrev.:Tetrahedron
Volume:58
Issue / Number:32
Start Page:6373
End Page:6380
Review Status:Peer-review
Audience:Experts Only
Abstract / Description:Palladium catalyzed Suzuki- and Negishi cross coupling reactions are used to convert the now readily available 3,4- dibromopyrrole derivatives 13 and 26 into the core structures of different pyrrole alkaloids. Several compounds of this series exhibit respectable cytotoxicity and resensitize multidrug resistant (MDR) cancer cell lines at non-toxic concentrations. Cytotoxicity and MDR reversal can be efficiently uncoupled by per-O-methylation of the peripheral hydroxyl groups. For the storniamide core structure 9 it is demonstrated that this chemical modification goes hand in hand with a complete loss of the DNA-cleaving capacity of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.
Free Keywords:cross coupling; DNA; natural products; palladium; pyrrole
Comment of the Author/Creator:Date: 2002, AUG 5
External Publication Status:published
Document Type:Article
Communicated by:N. N.
Affiliations:MPI für Kohlenforschung
Identifiers:ISI:000177217500015 [ID No:1]
ISSN:0040-4020 [ID No:2]
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