Synthesis of New Quinoline Derivatives as Inhibitors of Human Tumor Cells Growth

Abstract

A series of new 8-[(2H-tetrazol-5-yl)methoxy]quinoline derivatives, their sugar hydrazones, and their N-glycoside derivatives were synthesized. Furthermore, the 1,2,4-triazole-3-one derivatives 3 and 4 were synthesized from the amidrazone derivative 2. Some of the newly prepared compounds demonstrated inhibitory effects on the growth of MCF-7 human breast cancer cells as compared with the activity of the commonly used anticancer drug, cisplatin. The results of antitumor evaluation revealed that compounds 2-5, 8b, and 12 inhibited the growth of cancer cells through their effect as free-radical regulators by increasing the activity of superoxide dismutase and depletion of intracellular levels of reduced glutathione, catalase and glutathione peroxidase activities, accompanied with a high production of hydrogen peroxide, nitric oxide, and other free radicals causing the killing of tumor cells. The results suggested that the prepared compounds possess significant anticancer activity comparable to cisplatin and the antitumor activity of these prepared compounds was accompanied with a reduction in the levels of protein and nucleic acids.

Synthesis and Anti‐Avian Influenza Virus (H5N1) Evaluation of Some Novel Nicotinonitriles and Their N‐Acylic Nucleosides

“…On the other hand, the 4,6‐bis(4‐chlorophenyl)‐2‐(2,3,4,5,6‐pentahydroxyhexylidene) hydrazinyl)‐nicotinonitriles ( 17 ) was prepared by heating compound 6 with D ‐glucose (Scheme ). The formed product revealed absorption frequencies due to OH, NH, CN, and C═N in IR spectrum and its 1 H NMR spectrum showed the presence of the sugar protons, NH, and azomethine (CH═N) . Acetylation of the hydrazone derivative 17 by heating in acetic anhydride gave its corresponding O ‐acetylated sugar hydrazone derivative 18 .…”

Evaluation of cytotoxicity of propofol and its related mechanism in glioblastoma cells and astrocytes

“…Our data reveal that propofol increased SOD levels but decreased GPx and CAT levels in GBM 8401 cells. Previous studies have shown that quinoline derivatives induced the oxidative stress by increasing SOD activities but decreasing CAT and GPx activities, accompanied by a high production of H 2 O 2 which caused human breast cancer cell death . Therefore, this study implies that activities of GPx and CAT (H 2 O 2 ‐detoxifying enzymes) decreased with propofol, while activities of SOD (a ‐converting enzyme) increased with propopol which possibly led to H 2 O 2 accumulation and subsequently caused GBM 8401 cell death.…”

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

“…Keeping above in mind, we decided to synthesize conjugates of the above-mentioned moieties to study the biological profile of the resulting product. Genesis of our chemistry is derived from the fact that few earlier conjugates of 1,2,4-triazole and quinoline, where these molecules are linked via oxygen-or amide-containing linkers in a single frame, are known to possess biological activities like antimalarial 34 , antimicrobial 35 , anti tubercular 36 , antitumor 37,38 and antiviral 39 . However, the literature data about molecules that contain both of these bioactive ligands directly linked/bonded to each other in a single molecular frame are unknown.…”