Synthesis, FTIR, 13C-NMR and Temperature-Dependent 1H‑NMR Characteristics of Bis-naphthalimide Derivatives

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.

Physicochemical and biological interactions between cerium oxide nanoparticles and a 1,8-naphthalimide derivative

“…The C H asymmetric and symmetric stretching vibration bands of the methylene groups of N-substituents laid in the 3000-2850 cm −1 region. These assignments are all in agreement with those results published by Grzesiak and Brycki [43] and Philipova [44] who did a deep FTIR analysis of some derivative of N-substituted-1,8naphtalimides. The observed spectroscopic properties of ANN, namely absorption and fluorescence spectrum, quantum yield and fluorescence lifetime are presented in Table 1.…”

Naphthalimide-based optical turn-on sensor for monosaccharide recognition using boronic acid receptor

“…Naphthalimide dye has absorption and emission in the visible region with a large Stokes' shi to prevent self-quenching. [19][20][21][22][23][24] The synthesis and application of various types of naphthalimide dyes in different optical and electrochemical sensors had already been undertaken by our team. [25][26][27][28][29] In designing a uorescent probe to detect saccharides, there is an important challenge which is related to minor uorescence variations when attached with diols like sugars.…”