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

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, vol. 70, No 5, p. 635-648. ISSN 0366-6352. doi:10.1515/chempap-2015-0230. 2016.

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

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: Germany
• Confidentiality degree: is not subject to a state or trade secret
• WWW: 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
• Tags: AKR, rivok

Abstract

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.