Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216224%3A14310%2F16%3A00089211" target="_blank" >RIV/00216224:14310/16:00089211 - isvavai.cz</a>
Result on the web
<a href="http://www.degruyter.com/view/j/chempap.ahead-of-print/chempap-2015-0230/chempap-2015-0230.xml" target="_blank" >http://www.degruyter.com/view/j/chempap.ahead-of-print/chempap-2015-0230/chempap-2015-0230.xml</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1515/chempap-2015-0230" target="_blank" >10.1515/chempap-2015-0230</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
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Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemical Papers
ISSN
0366-6352
e-ISSN
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Volume of the periodical
70
Issue of the periodical within the volume
5
Country of publishing house
DE - GERMANY
Number of pages
14
Pages from-to
635-648
UT code for WoS article
000376512000013
EID of the result in the Scopus database
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