Synthesis of new 5-bromo derivatives of indole and spiroindole
phytoalexins

J 2016

Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins

OČENÁŠOVÁ, Lucia, Peter KUTSCHY, Jozef GONDA, Martina PILÁTOVÁ, Gabriela GÖNCIOVÁ et. al.

Basic information

Original name

Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins

Authors

OČENÁŠOVÁ, Lucia (703 Slovakia), Peter KUTSCHY (703 Slovakia), Jozef GONDA (703 Slovakia), Martina PILÁTOVÁ (703 Slovakia), Gabriela GÖNCIOVÁ (703 Slovakia), Jan MOJŽÍŠ (703 Slovakia) and Pavel PAZDERA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Chemical Papers, deGruyter, 2016, 0366-6352

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 1.258

RIV identification code

RIV/00216224:14310/16:00089211

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1515/chempap-2015-0230

UT WoS

000376512000013

Keywords in English

5-bromobrassinin; spiroindole phytoalexins; bromination; spirocyclisation; anti-proliferative activity

Abstract

V originále

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.

Citovat

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. 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.

@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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