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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 a Pavel PAZDERA. Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins. \textit{Chemical Papers}. deGruyter, 2016, roč.~70, č.~5, s.~635-648. ISSN~0366-6352. Dostupné z: https://dx.doi.org/10.1515/chempap-2015-0230.
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