Synthesis of hybrids between the alkaloids rutaecarpine and luotonins A, B |
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Authors: | Máté Bubenyák Melinda Pálfi Szabolcs Béni Béla Noszál |
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Institution: | a Department of Pharmaceutical Chemistry, Semmelweis University, H?gyes E. u. 9., Budapest H-1092, Hungary b Department of Pharmacodynamics, Semmelweis University, Nagyvárad tér 4., Budapest H-1089, Hungary |
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Abstract: | The synthesis of 7,12-dihydroindolo2′,3′:3,4]pyrrolo2,1-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. |
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Keywords: | Hybrid alkaloid Rutaecarpine Luotonin Bouchardatine Apoptosis Norrutaecarpine |
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