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 - Apr 18 2017

Keywords

  • 1,3-Thiazino[5,6-b]indole-4-ones
  • H and C NMR
  • Indole-2-carboxamide moiety
  • IR
  • Phytoalexin isomeric analogs

ASJC Scopus subject areas

  • Organic Chemistry

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