Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives

Abstract

BackgroundCoumarin and its derivatives are biologically very active. It was found that the enhanced activities are dependent on the coumarin nucleus. Biological significance of these compounds include anti-bacterial, anti-thrombotic and vasodilatory, anti-mutagenic, lipoxygenase and cyclooxygenase inhibition, scavenging of reactive oxygen species, and anti-tumourigenic. Our interest in medicinal chemistry of dicoumarol compounds have been developed by keeping in view the importance of coumarins along with its derivatives in medicinal chemistry. All the synthesized compounds were fully characterized by spectroscopic and analytical techniques and were screened for antimicrobial and U2OS bone cancer activities.Results4-hydroxycoumarin was derivatized by condensing with different aldehydes yielding the dicoumarol and translactonized products. Elemental analyses, ESI(+,−) MS, 1H and 13C{1H}-NMR, infrared spectroscopy and conductance studies were used to characterize the synthesized compounds which revealed the dicoumarol and dichromone structures for the compounds. The compounds were screened against U2OS cancerous cells and pathogenic micro organisms. The compounds with intermolecular H-bonding were found more active revealing a possible relationship among hydrogen bonding, cytotoxicity and antimicrobial activities.ConclusionCoumarin based drugs can be designed for the possible treatment of U2OS leukemia.

New dicoumarol sodium compound: crystal structure, theoretical study and tumoricidal activity against osteoblast cancer cells

“…The dicoumarol ligand ( L ) was synthesized by the reported procedure [51], 25 mmol benazldehyde was added to the 50 mmol stirred ethanolic solution of 4-hydroxycoumarin and the mixture was refluxed for 3 hr at 80°C. After cooling the reaction mixture, solid white powder of the L were isolated, washed several times with copious 10% ethanolic n-hexane solution.…”

Crystal structure of the triethylammonium salt of 3-[(4-hydroxy-3-methoxyphenyl)(4-hydroxy-2-oxo-2H-chromen-3-yl)methyl]-2-oxo-2H-chromen-4-olate

“…4-Hydroxy coumarine and its derivatives have been developed and exploited by various researchers in this context (Nolan et al, 2007;Tavolari et al, 2008;Jung & Park, 2009;Li et al, 2015;David, 2017). In biological tests with 3,3 0 -[(3methoxy-4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2Hchromen-2-one), much lower than expected cytotoxic activity was found (Rehman et al, 2013), which may be attributed to insufficient solubility. The hydrophobic nature of this compound is most likely due to strong intramolecular hydrogen bonding between the two coumarol moieties via two O-HÁ Á ÁO C interactions, which was confirmed for the solid state by X-ray structural analysis of this compound (Bandyopadhyay, 2015) and close relatives (Manolov et al, 2006;Stanchev et al, 2007).…”

“…3,3 0 -[(3-Methoxy-4-hydroxyphenyl)methanediyl]bis(4-hydroxy-2H-chromen-2-one) was synthesized following essentially the reported procedure (Rehman et al, 2013). 20 mmol of 3-methoxy-4-hydroxybenzaldehyde dissolved in anyhydrous ethanol was added to 50 mmol of an ethanolic solution of 4-hydroxycoumarin.…”

Automated noninvasive epithelial cell counting in phase contrast microscopy images with automated parameter selection

“…The U2OS human bone epithelial osteosarcoma cell line was derived from bone tissue of a 15-year-old female patient (Ponten & Saksela, 1967). U2OS cells are commonly used to model osteoblast behaviour in vitro (Rehman et al, 2013). U2OS cells were maintained in McCoy's 5A Modified Medium with L-glutamine and sodium bicarbonate supplemented with 10 mL L -1 penicillin-streptomycin and 10% FCS.…”