Synthesis of hybrids between the alkaloids rutaecarpine and luotonins A, B

Máté Bubenyák, Melinda Pálfi, Mária Takács, S. Béni, É. Szökő, B. Noszál, J. Kökösi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The synthesis of 7,12-dihydroindolo[2′,3′:3,4]pyrrolo[2,1-b]quinazolin-5-one, a hybrid compound containing common structural features of the natural alkaloids rutaecarpine (Evodia rutaecarpa) and luotonin A (Peganum nigellastrum), was performed by active methylene group transformations of deoxyvasicinone. The synthesis of 7-hydroxy-8-norrutaecarpine was accomplished via the first total synthesis of bouchardatine (Bouchardatia neurococca) and its acid-catalyzed ring closure. The synthesized alkaloid analogues are the first representatives of a new heterocyclic ring system. Preliminary testing of the synthesized compounds showed cytotoxic activities against HeLa cells and apoptosis inducing effects at a concentration comparable to that of the control drug, etoposide.

Original languageEnglish
Pages (from-to)4937-4940
Number of pages4
JournalTetrahedron Letters
Volume49
Issue number33
DOIs
Publication statusPublished - Aug 11 2008

Fingerprint

Alkaloids
Peganum
Evodia
Drug and Narcotic Control
Etoposide
HeLa Cells
Apoptosis
Acids
Testing
Pharmaceutical Preparations
rutecarpine
luotonin A
2,3-trimethylene-4-quinazolone

Keywords

  • Apoptosis
  • Bouchardatine
  • Hybrid alkaloid
  • Luotonin
  • Norrutaecarpine
  • Rutaecarpine

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of hybrids between the alkaloids rutaecarpine and luotonins A, B. / Bubenyák, Máté; Pálfi, Melinda; Takács, Mária; Béni, S.; Szökő, É.; Noszál, B.; Kökösi, J.

In: Tetrahedron Letters, Vol. 49, No. 33, 11.08.2008, p. 4937-4940.

Research output: Contribution to journalArticle

Bubenyák, Máté ; Pálfi, Melinda ; Takács, Mária ; Béni, S. ; Szökő, É. ; Noszál, B. ; Kökösi, J. / Synthesis of hybrids between the alkaloids rutaecarpine and luotonins A, B. In: Tetrahedron Letters. 2008 ; Vol. 49, No. 33. pp. 4937-4940.
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