Antioxidant, antibacterial, and cytotoxic activities of cimemoxin derivatives and their molecular docking studies

Purpose: The cimemoxin derivatives and their biological importance in antioxidant, antibacterial, and cytotoxic activities were the main focus of this study. By using a one-step reaction and green chemistry method, this study was able to synthesise derivatives of cimemoxin-related Mannich base compounds. Methods: Green chemistry can be used to prepare new, one-pot syntheses of cimemoxin derivatives (1a-i) Mannich base derivatives. FTIR, mass spectrometry, elemental analysis, and 1H and 13C NMR were used to analyse the newly synthesised compounds. The cytotoxic, antibacterial, and antioxidant activities of synthesized compounds (1a-i) were investigated. To test all synthesised compounds (1a–i) for cytotoxicity against normal Vero cell lines and MCF-7, the antioxidant activities were studied using DPPH, NO, H2O2, and ABTS•+ assays. The synthesised compounds were screened for anti-tyrosinase and antibacterial activities. Highly active compounds were investigated using molecular docking studies. Results: The compound 1h showed considerable activity in H2O2 (IC50: 13.79 µg/mL) and DPPH-scavenging was significantly active (IC50: 19.62 µg/mL) compared to the standard BHT (IC50: 27.16 and 33.88 µg/mL). Compound 1f was more effective than trolox (85.28 %) against ABTS and AAPH antioxidants. The most potent inhibitory activity was observed for compound 1h (IC50 = 15.16 µg/mL) which was more potent than kojic acid (IC50 = 17.79 ± 0.95 µg/mL). All synthetic substances were tested for their cytotoxic potential. Compound 1f (IC50 = 0.12 µg/mL) was extremely active compared to doxorubicin (IC50 = 0.74 µg/ml) and other compounds were lowly active compared to the MCF-7 cell line. In terms of anti-tyrosinase activity, compound 1h was highly active compared with the standard, and compound 1d was highly active against K. pneumonia. Conclusion: In this study, strong antioxidant, antibacterial, and cytotoxic activities were reported for all the compounds. In molecular docking studies, compounds 1d and 1h had higher binding affinities than the other compounds. Compounds 1d and 1h performed well in all tests. Additionally, this investigation successfully identified a number of intriguing compounds with cytotoxic and antioxidant properties

Synthesis of anthraquinone-connected coumarin derivatives via grindstone method and their evaluation of antibacterial, antioxidant, tyrosinase inhibitory activities with molecular docking, and DFT calculation studies

Anthraquinones and coumarins have excellent pharmacological activities and are an important class of natural plant metabolites with various biological activities. In this study, anthraquinone-9,10-dione and coumarin derivatives were combined to develop a novel anthraquinone-connected coumarin-derivative sequence. The synthesised novel anthraquinone-connected coumarin derivatives (1a-t) were screened for in vitro antibacterial, antioxidant, and tyrosinase inhibitory activities. The antibacterial activities of the synthesised compounds (1a–t) were tested against both gram-positive and gram-negative bacteria. Specifically, compound 1t was more active against E. aerogenes than ciprofloxacin. With regard to antioxidant activity, compound 1o (50.68 % at 100 μg/mL) was highly active compared to the other compounds, whereas it was less active than the standard BHT (76.74 % at 100 μg/mL). In terms of compound 1r (9.31 ± 0.45 μg/mL) was highly active against tyrosinase inhibitory activity compared with kojic acid (10.42 ± 0.98 μg/mL). In the molecular docking study, compound 1r had a higher docking score (−8.8 kcal mol−1) than kojic acid (−1.7 kcal mol−1). DFT calculations were performed to determine the energy gap of highly active compound 1r (ΔE = 0.11) and weakly active compound 1a (ΔE = 0.12). In this study, we found that every molecule displayed significant antibacterial, antioxidant, and tyrosinase inhibitory properties. Based on these reports, compounds 1r and 1t may act as multi-target agents