Bioisosteric modification on melatonin: synthesis of new naphthalene derivatives, in vitro antioxidant activity and cytotoxicity studies

Abstract

Melatonin (MLT) is a strong free radical scavenger that protects the body from the deleterious effects of excess oxidants. Synthesis of MLT analogue compounds with antioxidant potency has recently attracted the interest of researchers. In general, the strategy consists of modifying the groups in the different sites of the indole ring or replacing the indole ring with an analogue. As part of our ongoing research, the antioxidant capacity and cytotoxicity of newly synthesized MLT analogue naphthalene derivatives were evaluated. The radical scavenging activity was tested by a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. Most of the synthesized compounds showed significant antioxidant activity in comparison to MLT. The structure-activity relationship was identified. The in vitro cytotoxic effects of the synthesized compounds were also investigated in CHO-K1 cells using the MTT assay.

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“…According to the study, these compounds were shown to be extremely potent antioxidant agents. The authors attribute the enhanced activity to the lack of the 6-methoxy group and the substitution of the indole ring with that of albocarbon [54].…”

Design, Microwave-Assisted Synthesis, Antimicrobial and Anticancer Evaluation, and In Silico Studies of Some 2-Naphthamide Derivatives as DHFR and VEGFR-2 Inhibitors

“… 7 , 8 In addition, the naphthamide derivatives showed a large spectrum of activities in various pharmacological fields like anticancer, 9 − 12 antibacterial, 13 − 15 antifungal, 15 − 17 anti-inflammatory, 18 and antioxidants. 19 Moreover, many important drugs used therapeutically in the research area contain naphthalene moieties such as nafcillin, bedaquiline, naproxen, tolnaftate, duloxetine, and propanolol ( Figure 1 ).…”

“…Naphthalene is the simplest polycyclic aromatic hydrocarbon consisting of a fused pair of benzene rings. On the other hand, naphthamide derivatives containing a naphthalene nucleus are a common structural framework in various biologically active natural products, pharmaceuticals, and materials. , In addition, the naphthamide derivatives showed a large spectrum of activities in various pharmacological fields like anticancer, − antibacterial, − antifungal, − anti-inflammatory, and antioxidants . Moreover, many important drugs used therapeutically in the research area contain naphthalene moieties such as nafcillin, bedaquiline, naproxen, tolnaftate, duloxetine, and propanolol (Figure ).…”

Naftalenilmetilen Hidrazin Türevlerinin Antimikrobiyal Aktiviteleri

“…All of the tested compound in this study were synthesized and characterized on the basis of 1 H, 13 C NMR, mass spectra and elemental analysis. Thus, all data related on synthesis has been published (Shirinzadeh and Ghalia et al, 2020).…”