Syntheses, characterization, and anti-cancer activities of pyridine-amide based compounds containing appended phenol or catechol groups

Abstract

Several pyridine-amide compounds appended with phenol/catechol groups are synthesized. These compounds consist of protected or deprotected phenol/catechol groups and offer pyridine, amide, and phenol/catechol functional groups. All compounds have been well-characterized by various spectroscopic methods, elemental analysis, thermal studies, and crystallography. The biological activities of all compounds were investigated while a few compounds significantly decreased the metabolic viability, growth and clonogenicity of T98G cells in dose dependent manner. Accumulation of ROS was observed in T98G cells, which displayed a compromised redox status as evident from increased cellular Caspase 3/7 activity and formation of micronuclei. The in silico pharmacokinetic studies suggest that all compounds have good bioavailability, water solubility and other drug-like parameters. A few compounds were identified as the lead molecules for future investigation due to their: (a) high activity against T98G brain, H-460 lung, and SNU-80 thyroid cancer cells; (b) low cytotoxicity in non-malignant HEK and MRC-5 cells; (c) low toxic risks based on in silico evaluation; (d) good theoretical oral bioavailability according to Lipinski 'rule of five' pharmacokinetic parameters; and (e) better drug-likeness and drug-score values.

Kinetic study on electrochemical oxidation of catechols in the presence of cycloheptylamine and aniline: Experiments and digital simulation

“…2 4 Some pharmacological effects of catecholic drugs are adrenergic (isoproterenol, epinephrine, dopamine), antioxidant (gossypol, baicalein), antiasthmatic ((r)-isoproterenol, levisoprenaline), antibiotic (cefetecol, fomidacillin), enzyme inhibitor (benserazide, carbidopa) 1 and anticancer activities. 5 Catechols can be easily oxidized electrochemically to o-benzoquinones at low oxidation potentials in mild media. 6 Based on many evidences, o-benzoquinone undergoes a coupling reaction with anionic and dianionic species of catechol to form C-C or C-O bond.…”

Design, synthesis, and insecticidal activity of novel isoxazole derivatives containing bisamide moiety

“…Isoxazole, an important scaffold for synthesis of various active molecules and their derivatives, had a broad spectrum of bioactivities, such as antibacterial, antifungal, insecticide, and antiviral activities. Meanwhile, amide and their derivatives, which represented a key moiety in heterocyclic chemistry, played a leading role in pharmaceuticals and pesticides chemistry due to their potent bioactivities including antifungal, antibacterial, anticancer, antioxidant, and insecticidal activities. In our previous work, we had reported a series of novel isoxazole derivatives containing an amide moiety (Figure ) with potent antiviral activity against tobacco mosaic virus (TMV) …”

SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF SUBSTITUTED 2-Phenoxy-Nicotinaldehydes AS Α-Amylase INHIBITOR

“…12 In the recent past, novel derivatives of pyridine have been developed and found to have a large number of biological activities. [13][14][15][16][17][18][19][20] The pyridine structure is found in natural compounds like nicotinic acid (vitamin B3) and pyridoxine (vitamin B6). Over 100 medications on the market today include pyridine rings, such as Lunesta, commonly used to treat insomnia, Singulair, widely used to treat asthma, Nexium, widely used to treat acid reflux, and Actos, widely used to treat Type II diabetes ( Figure 1).…”