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.

Základní údaje

Originální název

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

Autoři

OČENÁŠOVÁ, Lucia (703 Slovensko), Peter KUTSCHY (703 Slovensko), Jozef GONDA (703 Slovensko), Martina PILÁTOVÁ (703 Slovensko), Gabriela GÖNCIOVÁ (703 Slovensko), Jan MOJŽÍŠ (703 Slovensko) a Pavel PAZDERA (203 Česká republika, garant, domácí)

Vydání

Chemical Papers, deGruyter, 2016, 0366-6352

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 1.258

Kód RIV

RIV/00216224:14310/16:00089211

Organizační jednotka

Přírodovědecká fakulta

DOI

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

UT WoS

000376512000013

Klíčová slova anglicky

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

Štítky

AKR, rivok

Změněno: 14. 4. 2017 11:43, Ing. Andrea Mikešková

Anotace

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 a Pavel PAZDERA. Synthesis of new 5-bromo derivatives of indole and spiroindole phytoalexins. 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.

@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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