Synthesis and antitumoral evaluation of indole alkaloid analogues containing an hexahydropyrrolo[1′,2′,3′:1,9a,9]imidazo[1,2-a]indole skeleton
| Autor: | Pilar Ventosa-Andrés, Ángel M. Valdivielso, M. Teresa García-López, Juan A. González-Vera, Rosario Herranz |
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| Rok vydání: | 2008 |
| Předmět: |
Magnetic Resonance Spectroscopy
Cell Survival Stereochemistry Clinical Biochemistry Pharmaceutical Science Antineoplastic Agents Biochemistry Chemical synthesis Indole Alkaloids Amidine Structure-Activity Relationship chemistry.chemical_compound Bromide Cell Line Tumor Nitriles Drug Discovery Humans Molecular Biology Indole test Molecular Structure Indole alkaloid Alkaloid Organic Chemistry Halogenation chemistry Electrophile Molecular Medicine |
| Zdroj: | Bioorganic & Medicinal Chemistry. 16:9313-9322 |
| ISSN: | 0968-0896 |
| DOI: | 10.1016/j.bmc.2008.08.070 |
| Popis: | The scope of acid-mediated cyclative additions of electrophiles to tryptophan-derived α-amino nitriles for the synthesis of 10 b -substituted-1,2,4,5,10 b ,10 c -hexahydropyrrolo[1′,2′,3′:1,9 a ,9]imidazo[1,2- a ]indoles analogues of indole alkaloids has been studied. The results demonstrate the high potential of the methodology for the synthesis of 10 b -bromo-derivatives, by bromination with NBS, 10 b -allyl-derivatives, by bromo-allyl exchange, and 10 b -prenyl-derivatives, by reaction with prenyl bromide in the presence of Mg(NO 3 ) 2 ·6H 2 0. Some of the new pyrroloimidazoindole derivatives displayed moderate μM cytotoxicities in human cancer cell lines and at 10 μg/mL inhibited more than 50% EGFR or HIF-1α. |
| Databáze: | OpenAIRE |
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