Antibacterial and Cytotoxic Activity of Ruthenium‐p‐cymene Complexes with 2‐Methylquinolin‐8‐ol Derivatives

Abstract

Eight 5‐aryl‐2‐methylquinolin‐8‐ol ligands (2–9) were prepared by a cross‐coupling Suzuki reaction from precursors brominated at position 5 (10), and positions 5 and 7 (11). These ligands were converted into new ruthenium(II)‐p‐cymene complexes (12–22) (51–94 %). The cytotoxic and antimicrobial activities of all compounds were investigated. Ligands showed higher cytotoxicity (EC50=3.1–4.8 μM) than ruthenium complexes (EC50=5.2–7.8 μM) against human melanoma cancer cells (A375). The most potent compound 7 has been shown to act via apoptosis. Some compounds were more potent as anticancer than cisplatin. Several ruthenium complexes selectively inhibited S. typhimurium and S. aureus (IC50=4.64–146.15 and 9.37–125.95 μg/mL, respectively), while most ligands were potent against C. albicans. Molecular docking studies with a protein from S. aureus suggest four key amino acids interactions, in agreement with the inhibitory potential against this bacterium.

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

“…Methods for introducing halogens into organic compounds are useful in organic synthesis, since halogen atoms can be further replaced by other functional groups, so that halogenated compounds are often required as synthetic intermediates [345][346][347]. Moreover, many bioactive compounds feature halogen atoms [348].…”

Gastroprophylactic Effects of p-Cymene in Ethanol-Induced Gastric Ulcer in Rats

“…The compound p-Cymene [1-methylethyl-4-(1-methylethyl)-benzen] has been known as a natural compound and a monoterpene that has toluene substituted by an isopropyl repositioning at the fourth sub-group (Figure 1). p-Cymene is an important monoterpene compound present in essential volatile oils of various aromatic medicinal plants and occurs naturally in innumerable foods [25]; moreover, it shows a wide spectrum of biological activities and is used in traditional medicines to convey analgesic [26], antioxidant [27], anti-inflammatory, anti-nociceptive, anxiolytic, anticancer, antimicrobial [28], and anti-tumor [29] actions, in addition to influencing the cardiovascular scheme [30] and central nervous scheme [31].…”

“…propyl repositioning at the fourth sub-group (Figure 1). p-Cymene is an important monoterpene compound present in essential volatile oils of various aromatic medicinal plants and occurs naturally in innumerable foods [25]; moreover, it shows a wide spectrum of biological activities and is used in traditional medicines to convey analgesic [26], antioxidant [27], anti-inflammatory, anti-nociceptive, anxiolytic, anticancer, antimicrobial [28], and anti-tumor [29] actions, in addition to influencing the cardiovascular scheme [30] and central nervous scheme [31]. Furthermore, p-Cymene is also an active molecule remote from numerous therapeutic plants conventionally used for the treatment of an extensive variety of chronic and/or communicable illnesses connected to pain, inflammation, and oxidative pressure, and can scavenge reactive oxygen species (ROS) avoiding oxidation of biomolecules and inducing pain and inflammation [26].…”