Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins
-
Lucia Očenášová
,
Peter Kutschy
Electrophilic aromatic substitution is one of the most thoroughly studied reactions in organic chemistry. In the present paper, the 5-brominated spirobrassinol methyl ethers VII, VIII were obtained by electrophilic substitution of the aromatic core of indoline at the C-5 position in the presence of various brominating agents. The same products were also prepared from 5-bromoindole (IX) following the sequence for the synthesis 1-methoxyspirobrassinol methyl ether (V) from indoline. In addition, the new related 5-bromospiroindoline derivatives XX–XXIII were synthesised and their biological activity on human tumour cell lines was examined. The presence of bromine in the indole or indoline skeleton at the C-5 position resulted in the partial increase in anticancer activity on leukaemia cell lines (Jurkat, CEM). The structures of the newly prepared products were determined by 1H and 13C NMR spectroscopy, including HSQC, HMBC, COSY, NOESY and DEPT measurements.
- †
Dr. Peter Kutschy passed away on 11 June 2012.
Acknowledgements.
The authors wish to express their gratitude to the Slovak Scientific Grant Agency (grant nos. 1/0954/12, 1/0322/14 and 1/398/14) and the Slovak Research and Development Agency (contract no. APVV-14-0883) for their financial support of this work. This work was also supported by the State NMR Programme no. 2003SP200280203 and VVGS PF 2012-31.
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© 2015 Institute of Chemistry, Slovak Academy of Sciences
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