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Coumarins from carcinogenic phenol: synthesis, characterization, in silico, biosafety, anticancer, antioxidant, and anti-inflammatory assessments

Yasser Fakri Mustafa

Department of Pharmaceutical Chemistry, College of Pharmacy, University of Mosul, Mosul, Iraq



Received: 28 July 2023  Accepted: 19 September 2023


Since 1947, a sterically hindered phenol named 3-(tert-butyl)-4-methoxyphenol, abbreviated here as 3-tBMP, has been widely used as a powerful preservative antioxidant for food, petrochemical, and pharmaceutical packaging. Then, the NIH considered 3-tBMP a human carcinogen based on animal experiments. This work aimed to transform this carcinogen into biosafe, biologically active coumarins using Pechmann condensation and thionyl chloride-promoted reactions. The molecular frameworks of the synthetic coumarins (CBMPa-CBMPd) were confirmed by various spectral detected instruments, including FTIR, 1H-NMR, and 13C-NMR. The in silico variables, biosafety, anticancer, antioxidant, and anti-inflammatory assessments regarding these coumarins are determined using two web-mediated free programs, two normal bacteriomers, three non-malignant cellular populations, six malignant ones, two phenotypes of free radicals, and three inflammation-mediated enzymes. The results showed that the synthetic coumarins, in particular CBMPa, showed good physicochemical and drug similarity properties in the computerized analysis. Additionally, despite the high concentrations used, the coumarins displayed biosafety profiles toward the normal bacteriomers and non-malignant cellular populations used. The constructed coumarins also displayed undetected anti-inflammatory traits along with potent antioxidant and anticancer attributes. Based on these findings, the author came to the conclusion that the carcinogenic phenol used in the experiment was converted into a biosafe antioxidant and anticancer agent with no discernible negative effects on the development of normal microbiota and healthy cellular populations. As a result, the coumarin backbone can act as a promising transformer of other phenols that cause malignancies.

Keywords: Anti-inflammatory; Antioxidant; Biosafety; Carcinogenic phenol; Coumarin

Full paper is available at

DOI: 10.1007/s11696-023-03105-7


Chemical Papers 78 (1) 493–504 (2024)

Wednesday, June 19, 2024

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