Thiazonaphthalimide derivatives: Synthesis and interaction with DNA

[Display omitted] •Thiazonaphtalimide derivatives were synthesized.•Exclusive formation of linear isomer was demonstrated by NMR and X-ray diffraction.•Photophysical properties and interaction with ct-DNA were studied. The synthesis of several thiazonaphthalimide derivatives is described. The exclus...

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Bibliographic Details
Published inTetrahedron letters Vol. 59; no. 26; pp. 2550 - 2553
Main Authors Botz, Alexandra, Chenavier, Yves, Pécaut, Jacques, Delangle, Pascale, Gateau, Christelle
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 27.06.2018
Elsevier
Subjects
1,8-Naphthalimide
Chemical Sciences
Chemistry
Chemistry, Organic
DNA
Fluorescence
Organic chemistry
Physical Sciences
Science & Technology
Thiazole formation
Fluorescence
1,8-Naphthalimide
Thiazole formation
DNA
HETEROCYCLES
AGENTS
ANTITUMOR-ACTIVITY
BINDING
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Summary:[Display omitted] •Thiazonaphtalimide derivatives were synthesized.•Exclusive formation of linear isomer was demonstrated by NMR and X-ray diffraction.•Photophysical properties and interaction with ct-DNA were studied. The synthesis of several thiazonaphthalimide derivatives is described. The exclusive formation of angular rather than linear isomers was unequivocally demonstrated by NMR and single crystal X-ray diffraction. Their photophysical properties and ability to bind calf-Thymus DNA with affinities in the range of 104 makes them interesting candidates to probe DNA by fluorescence.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2018.05.052