One-step template-directed synthesis of acridine-based rigid cyclophanes
Cyclo-bisintercalands are macrocyclic systems containing aromatic subunits, which are commonly used as hosts for aromatic molecules and as DNA intercalators. In this article, a step-by-step synthesis of a series of cyclo-bisintercalands containing 3,6-diaminoacridines as aromatic units, and connecte...
| Autores: | , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2012 |
| País: | España |
| Institución: | Universidad de Alcalá (UAH) |
| Repositorio: | e_Buah Biblioteca Digital Universidad de Alcalá |
| Idioma: | inglés |
| OAI Identifier: | oai:ebuah.uah.es:10017/65013 |
| Acceso en línea: | http://hdl.handle.net/10017/65013 https://dx.doi.org/10.1016/j.tet.2012.08.003 |
| Access Level: | acceso abierto |
| Palabra clave: | Cyclophanes Template effect Acridine Cyclo-bisintercalands Química Chemistry |
| Sumario: | Cyclo-bisintercalands are macrocyclic systems containing aromatic subunits, which are commonly used as hosts for aromatic molecules and as DNA intercalators. In this article, a step-by-step synthesis of a series of cyclo-bisintercalands containing 3,6-diaminoacridines as aromatic units, and connected by rigid spacers of different lengths, is reported. In addition, we describe herein a more efficient synthetic alternative, involving single-step template-directed processes. The new routes allow the easy synthetic access to these macrocyclic systems with acceptable yields. The synthesized cyclo-bisintercalands and their precursors have been structurally characterized by UV-visible and NMR methods. Preliminary biological activity assays performed on the bis- and cyclo-bisintercalands revealed interesting cytotoxic properties against different tumor cell lines, especially in the case of the bisintercalands, highlighting their potential as cancer chemotherapeutic agents. |
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