1263418-48-9Relevant academic research and scientific papers
Regiospecific Photocyclization of Mono- and Bis-Styryl-Substituted N-Heterocycles: A Synthesis of DNA-Binding Benzo[c]quinolizinium Derivatives
Aliyeu, Tseimur M.,Berdnikova, Daria V.,Fedorova, Olga A.,Gulakova, Elena N.,Stremmel, Christopher,Ihmels, Heiko
, p. 9075 - 9085 (2016)
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.
Spectroscopic Investigation and Photophysics of a D-π-A-π-D Type Styryl Pyrazine Derivative
El-Daly, Samy A.,Alamry, Khalid A.
, p. 163 - 176 (2016)
E,E-2,5-bis(3,4-dimethoxystyryl)pyrazine (BDSP) has been prepared by aldol condensation between 2,5-dimethypyrazine and 3,4-dimthoxybenzaldehyde and characterized by IR, 1H NMR, 13C NMR and X-ray crystallography. The electronic absor
Competition between methoxy-based and pyrazine-based synthons in methoxy-substituted distyrylpyrazines
Collas, Alain,Bagrowska, Izabela,Aleksandrzak, Krzysztof,Zeller, Matthias,Blockhuys, Frank
experimental part, p. 1299 - 1309 (2012/02/15)
Four new methoxy-substituted derivatives of E,E-2,5-bis(2-phenylethenyl) pyrazine have been synthesized. The supramolecular structures of the resulting set of five polymorphs have been studied using single-crystal X-ray diffraction to gauge the influence of the position of the methoxy groups on the organization of the molecules in the solid state, as part of an attempt to dispense with the particular polymorphism of the parent compound. The crystal packing patterns were analyzed in terms of the two pyrazine-based synthons found in the parent compoundss crystal structure, the πpyrazine...π phenyl stacking synthon, and the pyrazine hydrogen-bonded synthon, as well as in terms of weak intermolecular interactions such as CH...O, CH...N, and CH...π. The analysis shows that the introduction of methoxy groups in positions other than only the para position of the peripheral benzene rings successfully switches off the two synthons seen in the parent compound and that the new compounds adopt other packing strategies, based on methoxy...methoxy and -OCH3...π contacts. Polymorphism, however, remains.(Figure Presented)
