Investigation of chemical reactivity of 2-alkoxy-1,4-naphthoquinones and their anticancer activity

1,4-Naphthoquinone Analogues: Potent Antibacterial Agents and Mode of Action Evaluation

“…The mechanism of these antibacterial agents involves enhanced ROS generation and is followed by apoptotic cell death [6,7]. A number of compounds with a 1,4-naphthoquinone moiety can activate noticeable biological inhibitions such as antimicrobial [8], anticancer [9], antitubercular [10], antimalarial [11] and trypanocidal [12] activities. Due to the ability to generate ROS, naphthoquinone analogues are extremely cytotoxic to the infected cells and can restrict cellular enzymes, which are responsible for apoptosis and cell growth [13].…”

1,4-Naphthoquinones: Some Biological Properties and Application

“…11) showed higher susceptibility to bloodstream trypomastigotes and exhibited a greater efficacy against trypomastigotes from different T. cruzi of Brazil and CL strains through the induction of intracellular autophagy and elevation of ROS level, leading to parasite death. 66) 2.6. Cytotoxic and Anticancer Properties Many medicinal anticancer drugs based on natural compounds, such as menadione and anthracycline glycosides (doxorubicin, daunorubicin, aclacinomycin A), have a 1,4-naphthoquinoid fragment in their structure.…”

“…Using in silico molecular docking approach and pharmacological tests, the authors suggested that the active compounds may bind G protein-coupled receptor 55 (GPR55) and exert its pronounced antiproliferative activity against breast cancer cells. 84) Plumbagin (66) and menadione (67) (Fig. 16) were found to be toxic for C6 glioblastoma cells, increased the intracellular ROS amount, significantly uncoupled mitochondrial oxidation from phosphorylation impairing energy productions and caused cell death by necrosis.…”

“…1,4-Naphthoquinones as Biomedical Instruments The potential of some 1,4-naphthoquinones to rapidly visual- 5,8-Dihydroxy-1,4-naphthoquinone ize necrotic myocardium and the possible mechanisms of necrosis avidity was discovered. Not so long ago, six 1,4-naphthoquinones, 1,4-naphthoquinone (1), juglone (3), naphthazarin (4), plumbagin (66) and menadione (67) were radiolabeled with iodine-131; the necrotic myocardium imaging property and biodistribution of radio-labeled compounds were determined in rat models with re-perfused myocardial infarction. It was found that the necrotic myocardium could be clearly visualized by modern SPECT/CT tomography using this compound as early as 3 h post-injection.…”

Investigation of the antimicrobial and anticancer activity of aminonaphthoquinones

“…The 1,4‐naphthoquinones are the most significant and broadly dispersed chemical class in the quinone family. Their derivatives have been reported to have a range of biological activities such as antiallergic (Lien, Huang, Teng, Wang, & Kuo, ), antibacterial (Janeczko et al, ; Novais et al, ; Yildirim et al, ), anticancer (Benites, Valderrama, Ramos, Muccioli, & Buc Calderon, ; Manickam et al, ), dual anticancer and antibacterial (Bayrak et al, ), antifungal (Huang, Kuo, Hsiao, & Lin, ), anti‐inflammatory (Sasaki, Abe, & Yoshizaki, ; Tandon, Chhor, Singh, Rai, & Yadav, ), antithrombotic (Jin, Ryu, Moon, Cho, & Yun, ; Yuk et al, ), antiplatelet (da Silva et al, ; Lien et al, ), antiviral (Ilina et al, ; Inbaraj & Chignell, ; Tandon, Singh, Rai, Chhor, & Khan, ; Yuk et al, ), apoptotic (Gao, Hiromura, Yasui, & Sakurai, ; Kim et al, ; Kim et al, ), lipoxygenase inhibitory (Richwien & Wurm, ; Wurm & Schwandt, , radical scavenging (Song et al, ), and anti‐ringworm (Inbaraj & Chignell, ) activities.…”