Synthesis and in vitro antiproliferative effect of isomeric analogs of cyclobrassinin phytoalexin possessing the 1,3-thiazino[5,6-b]indole-4-one skeleton

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Abstract

Isomeric analogs of cyclobrassinin phytoalexin possessing the 1,3-thiazino[5,6-b]indole-4-one skeleton have been prepared. Starting from 1H-indole-2-carbonyl isothiocyanate, N-aryl-N′-(indole-2-carbonyl)-substituted thiourea or the corresponding S-aryl-N-(indole-2-carbonyl)dithiocarbamate intermediates were prepared and then transformed by ringclosure via Hugerschoff reaction with phenyltrimethylammonium tribromide. Attempted synthesis of N′-(indole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl)thiourea unexpectedly delivered the 2-(indole-2-carbonylamino)-5,6,7-trimethoxybenzothiazole ring system. The structures of the new ring systems were determined by means of IR and NMR spectroscopy. The new derivatives synthesized exert moderate in vitro antiproliferative effects on a panel of adherent human cell lines (HeLa, A2780, A431 and MCF7).

Original languageEnglish
Pages (from-to)1-11
Number of pages11
JournalArkivoc
Volume2017
Issue number4
DOIs
Publication statusPublished - ápr. 18 2017

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Thiourea
Nuclear magnetic resonance spectroscopy
indole
phytoalexins
cyclobrassinin
Infrared spectroscopy
Cells
Derivatives
phenyltrimethylammonium
isothiocyanic acid

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Synthesis and in vitro antiproliferative effect of isomeric analogs of cyclobrassinin phytoalexin possessing the 1,3-thiazino[5,6-b]indole-4-one skeleton",
abstract = "Isomeric analogs of cyclobrassinin phytoalexin possessing the 1,3-thiazino[5,6-b]indole-4-one skeleton have been prepared. Starting from 1H-indole-2-carbonyl isothiocyanate, N-aryl-N′-(indole-2-carbonyl)-substituted thiourea or the corresponding S-aryl-N-(indole-2-carbonyl)dithiocarbamate intermediates were prepared and then transformed by ringclosure via Hugerschoff reaction with phenyltrimethylammonium tribromide. Attempted synthesis of N′-(indole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl)thiourea unexpectedly delivered the 2-(indole-2-carbonylamino)-5,6,7-trimethoxybenzothiazole ring system. The structures of the new ring systems were determined by means of IR and NMR spectroscopy. The new derivatives synthesized exert moderate in vitro antiproliferative effects on a panel of adherent human cell lines (HeLa, A2780, A431 and MCF7).",
keywords = "1,3-Thiazino[5,6-b]indole-4-ones, H and C NMR, Indole-2-carboxamide moiety, IR, Phytoalexin isomeric analogs",
author = "P. Csom{\'o}s and L. Fodor and I. Zupk{\'o} and A. Cs{\'a}mpai and P. Soh{\'a}r",
year = "2017",
month = "4",
day = "18",
doi = "10.3998/ark.5550190.0018.400",
language = "English",
volume = "2017",
pages = "1--11",
journal = "Arkivoc",
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T1 - Synthesis and in vitro antiproliferative effect of isomeric analogs of cyclobrassinin phytoalexin possessing the 1,3-thiazino[5,6-b]indole-4-one skeleton

AU - Csomós, P.

AU - Fodor, L.

AU - Zupkó, I.

AU - Csámpai, A.

AU - Sohár, P.

PY - 2017/4/18

Y1 - 2017/4/18

N2 - Isomeric analogs of cyclobrassinin phytoalexin possessing the 1,3-thiazino[5,6-b]indole-4-one skeleton have been prepared. Starting from 1H-indole-2-carbonyl isothiocyanate, N-aryl-N′-(indole-2-carbonyl)-substituted thiourea or the corresponding S-aryl-N-(indole-2-carbonyl)dithiocarbamate intermediates were prepared and then transformed by ringclosure via Hugerschoff reaction with phenyltrimethylammonium tribromide. Attempted synthesis of N′-(indole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl)thiourea unexpectedly delivered the 2-(indole-2-carbonylamino)-5,6,7-trimethoxybenzothiazole ring system. The structures of the new ring systems were determined by means of IR and NMR spectroscopy. The new derivatives synthesized exert moderate in vitro antiproliferative effects on a panel of adherent human cell lines (HeLa, A2780, A431 and MCF7).

AB - Isomeric analogs of cyclobrassinin phytoalexin possessing the 1,3-thiazino[5,6-b]indole-4-one skeleton have been prepared. Starting from 1H-indole-2-carbonyl isothiocyanate, N-aryl-N′-(indole-2-carbonyl)-substituted thiourea or the corresponding S-aryl-N-(indole-2-carbonyl)dithiocarbamate intermediates were prepared and then transformed by ringclosure via Hugerschoff reaction with phenyltrimethylammonium tribromide. Attempted synthesis of N′-(indole-2-carbonyl)-N-(3,4,5-trimethoxyphenyl)thiourea unexpectedly delivered the 2-(indole-2-carbonylamino)-5,6,7-trimethoxybenzothiazole ring system. The structures of the new ring systems were determined by means of IR and NMR spectroscopy. The new derivatives synthesized exert moderate in vitro antiproliferative effects on a panel of adherent human cell lines (HeLa, A2780, A431 and MCF7).

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KW - H and C NMR

KW - Indole-2-carboxamide moiety

KW - IR

KW - Phytoalexin isomeric analogs

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