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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2016

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Chemical Papers

ISSN

0366-6352

e-ISSN

—

Svazek periodika

70

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

14

Strana od-do

635-648

Kód UT WoS článku

000376512000013

EID výsledku v databázi Scopus

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