ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7

Published monthly
 

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

Lucia Očenášová, Peter Kutschy, Jozef Gonda, Martina Pilátová, Gabriela Gönciová, Ján Mojžiš, and Pavel Pazdera

aDepartment of Organic Chemistry, Institute of Chemical Science, Faculty of Science, P. J. Šafárik University, Moyzesova 11, 040 01 Košice, Slovakia

 

E-mail: lucia.ocenas@gmail.com

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.

Keywords: 5-bromobrassinin – spiroindole phytoalexins – bromination – spirocyclisation – anti-proliferative activity

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0230

 

Chemical Papers 70 (5) 635–648 (2016)

Thursday, December 09, 2021

IMPACT FACTOR 2020
2.097
SCImago Journal Rank 2020
0.344
SEARCH
Advanced
VOLUMES
XXVIII. International Conference on Coordination and Bioinorganic Chemistry
© 2021 Chemical Papers