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Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives
Laboratory of Microbiocides Chemistry, Department of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
* Author to whom correspondence should be addressed.
Received: 5 September 2012; in revised form: 17 October 2012 / Accepted: 18 October 2012 / Published: 22 October 2012
Abstract: Chemotherapy is still the most important method of cancer treatment. To make this method more effective and safe, new drugs to destroy cancer cells are needed. Some bis-naphthalimide derivatives show potential anticancer activity via an intercalation mechanism. A higher degree of DNA intercalation corresponds to better therapeutic effects. The degree of intercalation of naphthalimides depends on their structure, molecular dynamics and intermolecular interactions with DNA. In order to apply any active substance as a drug, its molecular dynamics as well as possible interactions with target molecules have to be examined in exhaustive details. This paper describes a practical preparation of some novel bis-naphthalimide derivatives with different functional groups and their FTIR and 1H- and 13C-NMR spectral characteristics. To determine the molecular dynamics of the obtained compounds the temperature, their 1H-NMR spectra were measured. It has been clearly proven in this paper that the unusual temperature-dependent 1H-NMR behavior of the aromatic protons of phthalimide derivatives, previously described in the literature as “hypersensitivity” and explained by n-π interactions and molecular motions of aromatic amide rings, is a result of temperature driven changes of the geometry of carbonyl groups.
Keywords: bis-naphthalimide; 1H-NMR spectroscopy; FTIR spectra; anticancer activity; DNA; intercalator
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Grzesiak, W.; Brycki, B. Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives. Molecules 2012, 17, 12427-12448.
Grzesiak W, Brycki B. Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives. Molecules. 2012; 17(10):12427-12448.
Grzesiak, Waldemar; Brycki, Bogumił. 2012. "Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives." Molecules 17, no. 10: 12427-12448.