Benzo[c]phenanthrene derivatives: Synthesis, optical properties and cytotoxic activity

A new benzo[c]phenanthrene ketone has been synthesized through Heck coupling and oxidative photocyclization. The optical properties of the target tetracyclic system were also investigated by UV-visible absorption and photoluminescence spectroscopy and an emission in the visible region was observed. The tetracyclic ketone has been reacted with primary amines in the presence of Lewis acid followed by NaBH4 reduction to provide new polyaromatic secondary amines in good yields and purity. All the synthesized new compounds were identified and characterized through a combination of nuclear magnetic resonance spectroscopy and mass spectrometric methods. The cytotoxic activity of all pure benzo[c]phenanthrene derivatives has been evaluated against Hep-2 cell line using (MTT) colori­metric assay

7-Cyano-15-methoxy[6]helicene through a photochemical pathway and investigation of its chiroptical and photophysical properties

7-Cyano-15-methoxy[6]helicene was synthesized, in 54% overall yield, through a short photochemical procedure including mild conditions and inexpensive reagents. The desired helical hexacyclic framework was characterized by $^{1}\mathrm{H}$ and $^{13}\mathrm{C}$ NMR and mass spectroscopies. Single crystals of the helicene were also obtained and an X-ray diffraction analysis is presented. Enantiomers of the helicene were obtained in 100% $ee$ after separation by chiral HPLC and their chiroptical properties were experimentally investigated from optical rotatory dispersion and electronic circular dichroism (ECD). UV–Vis absorption and fluorescence properties of the helicene were evaluated in solutions and a strong emission was noted in the blue region of the visible spectrum . Its electrochemical behavior was also experimentally examined and HOMO and LUMO energy levels were estimated, showing an electrochemical band gap of 2.11 eV. The results obtained herein are helpful to explain the interest of cyano and methoxy groups in making the new material a good candidate to be used in optoelectronic applications

Novel functional [4]helicenes through a photooxidation pathway. Investigation of the absorption and fluorescence in solution

Novel functional [4]helicenes have been designed and synthesized, in 54%–72% overall yields, through an operational and simple two-step photochemical approach starting from various p-substituted phenylacetonitriles, and were characterized by NMR ($^{1}$H, $^{13}$C, and COSY) and FT-IR spectroscopies. UV–Vis absorption properties of these tetracyclic ${\pi }$-conjugated systems have been experimentally investigated in various solvents and their optical gap energy was estimated to be less than 3.28 eV. The photoluminescence properties of these molecules have been evaluated in solutions and an emission in the blue region of the visible spectrum was noted. The obtained results seem encouraging for the examination of such compounds as promising materials for optoelectronic applications

Novel functional [4]helicenes through a photooxidation pathway. Investigation of the absorption and fluorescence in solution

Novel functional [4]helicenes have been designed and synthesized, in 54%–72% overall yields, through an operational and simple two-step photochemical approach starting from various p-substituted phenylacetonitriles, and were characterized by NMR ($^{1}$H, $^{13}$C, and COSY) and FT-IR spectroscopies. UV–Vis absorption properties of these tetracyclic ${\pi }$-conjugated systems have been experimentally investigated in various solvents and their optical gap energy was estimated to be less than 3.28 eV. The photoluminescence properties of these molecules have been evaluated in solutions and an emission in the blue region of the visible spectrum was noted. The obtained results seem encouraging for the examination of such compounds as promising materials for optoelectronic applications

7-Cyano-15-methoxy[6]helicene through a photochemical pathway and investigation of its chiroptical and photophysical properties

7-Cyano-15-methoxy[6]helicene was synthesized, in 54% overall yield, through a short photochemical procedure including mild conditions and inexpensive reagents. The desired helical hexacyclic framework was characterized by $^{1}\mathrm{H}$ and $^{13}\mathrm{C}$ NMR and mass spectroscopies. Single crystals of the helicene were also obtained and an X-ray diffraction analysis is presented. Enantiomers of the helicene were obtained in 100% $ee$ after separation by chiral HPLC and their chiroptical properties were experimentally investigated from optical rotatory dispersion and electronic circular dichroism (ECD). UV–Vis absorption and fluorescence properties of the helicene were evaluated in solutions and a strong emission was noted in the blue region of the visible spectrum . Its electrochemical behavior was also experimentally examined and HOMO and LUMO energy levels were estimated, showing an electrochemical band gap of 2.11 eV. The results obtained herein are helpful to explain the interest of cyano and methoxy groups in making the new material a good candidate to be used in optoelectronic applications

Molecular docking investigation of cytotoxic phenanthrene derivatives

Our previous experimental work indicated that the presence of ester functionality in phenanthrene derivatives D-1 and D-2 leads to potent cytotoxicity against the Caco-2 cell line. The present work is based on th-is experimental result. First, we optimized the structures of the studied molecules using the density functional theory method. Then we performed a study about their potential biological importance by evaluating the binding mode and exploring their intermolecular interactions with appropriate proteins using molecular docking calculations. Consequently, we confirmed the results obtained from experimental studies. In particular, our study indicated that many promising proteins are able to bind and interact with the phenanthrene skeleton from the binding site. Methyl 8-methyl-9,10-phenanthrenequinone-3-carboxylate D-1 and methyl 8-methyldibenzo[a,c]phenazine-3-carboxylate D-2 displayed strong cytotoxicity. However, the best affinity is noted for B-Raf proto-oncogene serine/threonine-protein kinase (-9.8 Kcal/mol for molecule D-1 and -11.1 Kcal/mol for molecule D-2), which is higher than that of any other protein used. Especially, this protein is involved in sending signals inside cells that are involved in directing cell growth and is found to be a significant target in both types of studied cancers

Molecular docking investigation of cytotoxic phenanthrene derivatives

Our previous experimental work indicated that the presence of ester functionality in phenanthrene derivatives D-1 and D-2 leads to potent cytotoxicity against the Caco-2 cell line. The present work is based on th-is experimental result. First, we optimized the structures of the studied molecules using the density functional theory method. Then we performed a study about their potential biological importance by evaluating the binding mode and exploring their intermolecular interactions with appropriate proteins using molecular docking calculations. Consequently, we confirmed the results obtained from experimental studies. In particular, our study indicated that many promising proteins are able to bind and interact with the phenanthrene skeleton from the binding site. Methyl 8-methyl-9,10-phenanthrenequinone-3-carboxylate D-1 and methyl 8-methyldibenzo[a,c]phenazine-3-carboxylate D-2 displayed strong cytotoxicity. However, the best affinity is noted for B-Raf proto-oncogene serine/threonine-protein kinase (-9.8 Kcal/mol for molecule D-1 and -11.1 Kcal/mol for molecule D-2), which is higher than that of any other protein used. Especially, this protein is involved in sending signals inside cells that are involved in directing cell growth and is found to be a significant target in both types of studied cancers