Novel acenaphthopyrazine derivatives as antitumor agents against MCF-7 cells: molecular synthesis, optical properties, and DNA-binding studies |
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Authors: | Junling Xing Jingnan Cui Shuang Wang Jin Gao and Zhichao Zhang |
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Institution: | (1) State Key Laboratory of Fine Chemicals, Dalian University of Technology, PO Box 89, Zhongshan Road 158, Dalian, 116012, China; |
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Abstract: | Abstract A series of novel acenaphthopyrazine derivatives was synthesized from acenaphthylene-1,2-dione via three steps, including
bromination, cyclization, and SNArH reaction. These new compounds exhibited potential antiproliferative activity against MCF-7 cells in vitro, and 3-2-(dimethylamino)ethylamino]acenaphtho1,2-b]pyrazine-8,9-dicarbonitrile exhibited the highest activity (IC
50 = 4.60 μM). DNA-binding experiments suggested that these derivatives bind to DNA through intercalation with intrinsic binding
constants K all above 105 M−1. Optical property studies indicated that these compounds have long emission wavelength (λ
em > 560 nm), high quantum yields in toluene (Φf = 0.59 for 3-(morpholin-4-yl)acenaphtho1,2-b]pyrazine-8,9-dicarbonitrile), and large Stokes shift (ΔS > 130 nm). |
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