Issue 36, 2013
From the journal:

Organic & Biomolecular Chemistry

Doubly prenylated tryptamines: cytotoxicity, antimicrobial activity and cyclisation to the marine natural product flustramine A†

Santosh Kumar Adla,a   Florenz Sasse,b   Gerhard Kelter,c   Heinz-Herbert Fiebigc  and  Thomas Lindel*a  

* Corresponding authors

a Institute of Organic Chemistry, TU Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
E-mail: th.lindel@tu-braunschweig.de
Fax: (+49) 531-391-7744

b Department of Chemical Biology, Helmholtz Centre for Infection Research, Inhoffenstraße 7, 38124 Braunschweig, Germany

c Oncotest Institute for Experimental Oncology GmbH Am Flughafen 12-14, 79108 Freiburg, Germany

Abstract

The marine natural product flustramine A was synthesised via oxidative cyclisation of Nb-methylated 1-prenyl-2-tert-prenyl-6-bromotryptamine and subsequent reduction of the resulting amidinium salt. Only the tert-prenyl group migrated, whereas the 1-prenyl group remained in place. Interestingly, the 2-tert-prenylated precursor revealed to be the biologically most active of our entire series of 21 compounds. Required for cytotoxicity and antimicrobial activity was the presence of a non-cyclised tryptamine side chain carrying a free secondary amine, whereas the presence of a 6-bromo substituent did not enhance cytotoxicity. In a panel of 42 human tumor cell lines, most sensitive were the lung and mammary cancer cell lines LXFA629L (IC50 1.9 μM) and MAXF401NL (IC50 2.4 μM), respectively. In a serial dilution assay, satisfying IC50 values of 5.9 μM against Micrococcus luteus and 7.7 μM each against Mycobacterium phlei were determined for Nb-methyl-1-prenyl-2-tert-prenyl-6-bromotryptamine.

Graphical abstract: Doubly prenylated tryptamines: cytotoxicity, antimicrobial activity and cyclisation to the marine natural product flustramine A

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Article information

DOI
https://doi.org/10.1039/C3OB40896E
Article type
Paper
Submitted
30 Apr 2013
Accepted
23 Jul 2013
First published
23 Jul 2013

Org. Biomol. Chem., 2013,11, 6119-6130

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Doubly prenylated tryptamines: cytotoxicity, antimicrobial activity and cyclisation to the marine natural product flustramine A

S. K. Adla, F. Sasse, G. Kelter, H. Fiebig and T. Lindel, Org. Biomol. Chem., 2013, 11, 6119 DOI: 10.1039/C3OB40896E

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