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

Bubenyák, Máté Dániel and Pálfi, Melinda and Takács, Mária and Béni, Szabolcs and Szökő, Éva and Noszál, Béla and Kökösi, József (2008) Synthesis of hybrids between the alkaloids rutaecarpine and luotonins A, B. TETRAHEDRON LETTERS, 49 (33). pp. 4937-4940. ISSN 0040-4039

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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. (C) 2008 Elsevier Ltd. All rights reserved.

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