Novel Naphthalene Diimides Synthesis, and Characterization as Probable Anticancer Agents

Naphthalene diimides (NDIs) have outstanding conjugation and photophysical properties which offer marvelous applications in various facets of industry from medicine to electronics. In medicine, NDIs can be used to interact with the guanine quadruplex and inhibit the proliferation of cancer cells by impairing the function of the telomerase enzyme that is responsible for replenishing the base units at the end of telomeres. Moreover, they can inhibit the function of acetylcholinesterase in Alzheimer disease. In addition, because of π−acidic property of NDIs, they can be used as transmembrane anion transporters between lipid layers. In the present research, two symmetrical naphthalene diimides, 3 and 5, have been synthesized from the commercially available naphthalene dianhydride (NDA) with the primary amine in the presence of high boiling solvent. For compound 3, phosphate moiety was added to the imide positions in order to enhance the solubility in polar solvents. In the same way, for compound 5, adenine substituent was for being soluble in polar solvents and also was for having a strong interaction with the guanine quadruplex through π−π stacking, hydrogen bonding and other interactions. Optical properties for 3 and 5 in different solvents were measured. Compound 5 showed high molar absorptivity coefficient in the polar aprotic solvents such as DMAc, DMF and NMP. In addition to absorptivity coefficient, half width, oscillator strength and singlet energy were also being calculated. FT−IR was performed in order to confirm the structures. Accordingly, a great consistency can be seen between the spectrum and the compounds. Finally, we propose that the compounds might be used as anticancer agents and due to their planarity and rigidity of the molecules can also interact with the guanine quadruplex to prevent the telomerase to add base units and cause to cell division and proliferation.