Synthesis of bioisosteric 5-sulfa-rutaecarpine derivatives

Máté Bubenyák, Mária Takács, Balázs Blazics, Ákos Rácz, Béla Noszál, László Püski, József Kökösi, István Hermecz

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6 Citations (Scopus)

Abstract

Rutaecarpine (Evodia rutaecarpa) derivatives were synthesized by bioisosteric replacements of the quinazolone moiety of the pentacyclic system with benzothiadiazine 1,1-dioxide. Syntheses were performed efficiently by formation of phenylhydrazones via active methylene group transformations of pyrrolo-and pyrido[1,2-b]1,2,4-benzothiadiazine 5,5-dioxides, and subsequent Fischer-indolization. Preliminary testing of compound 3 showed cytotoxic activity against HeLa cells and apoptosis inducing effect.

Original languageEnglish
Pages (from-to)291-302
Number of pages12
JournalArkivoc
Volume2010
Issue number11
DOIs
Publication statusPublished - Nov 7 2010

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Keywords

  • Alkaloids
  • Antitumor agents
  • Benzothiadiazine
  • Bioisosteric replacements
  • Luotonin A
  • Rutaecarpine

ASJC Scopus subject areas

  • Organic Chemistry

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