Regiospecific Photocyclization of Mono- and Bis-Styryl-Substituted N-Heterocycles: A Synthesis of DNA-Binding Benzo[c]quinolizinium Derivatives
| Autor: | Christopher Stremmel, Daria V. Berdnikova, Tseimur M. Aliyeu, Olga A. Fedorova, Heiko Ihmels, Elena N. Gulakova |
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| Rok vydání: | 2016 |
| Předmět: |
Spectrometry
Mass Electrospray Ionization DNA synthesis 010405 organic chemistry Stereochemistry Chemistry Photochemistry Proton Magnetic Resonance Spectroscopy Organic Chemistry Intercalation (chemistry) DNA 010402 general chemistry 01 natural sciences 0104 chemical sciences chemistry.chemical_compound Cyclization Heterocyclic Compounds Benzoquinones Carbon-13 Magnetic Resonance Spectroscopy Styrene |
| Zdroj: | The Journal of organic chemistry. 81(19) |
| ISSN: | 1520-6904 |
| Popis: | Regiospecific C–N photocyclization of mono- and bis-styryl-substituted N-heterocycles was investigated. We demonstrated that the C–N regiospecificity of the photoinduced electrocyclization is a general feature of ortho-styryl-substituted N-heterocycles comprising one and two nitrogen atoms. This phototransformation provides a straightforward synthesis of the pharmaceutically important benzo[c]quinolizinium cation and its aza-analogues. Noticeably, bis-styryl derivatives undergo only one-fold cyclization with the second styryl fragment remaining uninvolved in the cyclization process. Photocyclization products of monostyryl derivativatives intercalate into calf thymus DNA (ct DNA), whereas photocyclization products of bis-styryl derivativatives possess a mixed binding mechanism with ct DNA. The results can be used for development of novel DNA-targeting chemotherapeutics based on benzo[c]quinolizinium derivatives. |
| Databáze: | OpenAIRE |
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