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@article{1320861, author = {Očenášová, Lucia and Kutschy, Peter and Gonda, Jozef and Pilátová, Martina and Gönciová, Gabriela and Mojžíš, Jan and Pazdera, Pavel}, article_number = {5}, doi = {http://dx.doi.org/10.1515/chempap-2015-0230}, keywords = {5-bromobrassinin; spiroindole phytoalexins; bromination; spirocyclisation; anti-proliferative activity}, language = {eng}, issn = {0366-6352}, journal = {Chemical Papers}, title = {Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins}, url = {http://www.degruyter.com/view/j/chempap.ahead-of-print/chempap-2015-0230/chempap-2015-0230.xml}, volume = {70}, year = {2016} }
TY - JOUR ID - 1320861 AU - Očenášová, Lucia - Kutschy, Peter - Gonda, Jozef - Pilátová, Martina - Gönciová, Gabriela - Mojžíš, Jan - Pazdera, Pavel PY - 2016 TI - Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins JF - Chemical Papers VL - 70 IS - 5 SP - 635-648 EP - 635-648 PB - deGruyter SN - 03666352 KW - 5-bromobrassinin KW - spiroindole phytoalexins KW - bromination KW - spirocyclisation KW - anti-proliferative activity UR - http://www.degruyter.com/view/j/chempap.ahead-of-print/chempap-2015-0230/chempap-2015-0230.xml L2 - http://www.degruyter.com/view/j/chempap.ahead-of-print/chempap-2015-0230/chempap-2015-0230.xml N2 - 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. ER -
OČENÁŠOVÁ, Lucia, Peter KUTSCHY, Jozef GONDA, Martina PILÁTOVÁ, Gabriela GÖNCIOVÁ, Jan MOJŽÍŠ and Pavel PAZDERA. Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins. \textit{Chemical Papers}. deGruyter, 2016, vol.~70, No~5, p.~635-648. ISSN~0366-6352. Available from: https://dx.doi.org/10.1515/chempap-2015-0230.
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