Design and synthesis of new coumarin–chalcone/NO hybrids of potential biological activity

El-Sherief, Hany A.M.; Abuo‐Rahma, Gamal El‐Din A.; Shoman, Mai E.; Beshr, Eman A. M.; Abd-Elbaky, Rehab Mahmoud

doi:10.1007/s00044-017-2004-9

Cited by 30 publications

(11 citation statements)

References 46 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pteryxin, a natural coumarin, is considered to be a stronger compound than 4‐aminopyridine derivatives in developing novel butyrylcholinesterase (BChE) inhibitors for AD treatment . A molecular hybridization strategy is a synthetic approach used to synthesize coumarin–chalcone hybrids that have shown moderate activity against CNS disease . Compound B , containing pyridine and a coumarin‐like skeleton, is considered in vivo as a modifying treatment for AD (Figure ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, CYP 450 evaluation, and docking simulation of novel 4‐aminopyridine and coumarin derivatives

Ghalehshahi

Balalaie

Sohbati

et al. 2019

Archiv der Pharmazie

View full text Add to dashboard Cite

Four series of novel compounds based on 4‐aminopyridine, glatiramer acetate, pyrone, and coumarin backbones were sufficiently synthesized and identified by spectroscopic methods. CYP enzyme inhibition assays of five predominate human P450 isozymes indicate that all compounds, except for 4‐hydrazide pyridine 1c, seem to be less toxic than 4‐aminopyridine. Further investigation of the compounds using molecular docking experiments revealed different, the same, or stronger binding modes for most of the synthesized compounds, with both polar and hydrophobic interactions with the 1WDA and 1J95 receptors compared to benzoyl l‐arginine amide and 4‐aminopyridine, respectively. These results introduce the synthesized compounds as K+ channel blockers that could be considered for in vivo CNS disease studies.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis, CYP 450 evaluation, and docking simulation of novel 4‐aminopyridine and coumarin derivatives

Ghalehshahi

Balalaie

Sohbati

et al. 2019

Archiv der Pharmazie

View full text Add to dashboard Cite

show abstract

“…The coumarin–chalcone hybrids 35 (MIC: 7.17–260.5 µg/ml) and their oxime‐containing analogs 36 (MIC: 1.15–243.4 µg/ml) possessed considerable activity against S. aureus , E. coli , P. aeruginosa , and K. pneumoniae , and the SAR indicated that the introduction of the oxime group could improve the activity against S. aureus significantly, but it could reduce the activity against Gram‐negative organisms. [ 86,87 ] Among them, hybrid 35a (MIC: 9.66–35.8 µg/ml) was comparable to or better than levofloxacin (MIC: 1.57–45 µg/ml) against S. aureus , E. coli , and K. pneumoniae , and hybrid 36a (MIC: 1.15 µg/ml) was 39.1 times more potent than levofloxacin against S. aureus .…”

Section: Coumarin–chalcone Hybridsmentioning

confidence: 99%

Coumarin‐containing hybrids and their antibacterial activities

Feng

Zhang

Yang

et al. 2020

Archiv der Pharmazie

View full text Add to dashboard Cite

Infections caused by Gram-positive and -negative bacteria are one of the foremost causes of morbidity and mortality globally. Antibiotics are the mainstay of therapy for bacterial infections, but the emergence and wide spread of drug-resistant pathogens have already become a huge issue for public healthcare systems. The coumarin moiety, which is ubiquitous in nature, could bind to the B subunit of DNA gyrase in bacteria and inhibit DNA supercoiling by blocking the ATPase activity; hence, coumarin derivatives possess potential antibacterial activity. Several coumarin-containing hybrids such as coumermycin A1, clorobiocin, and novobiocin have already been used in clinical practice for the treatment of various bacterial infections; thus, it is conceivable that hybridization of the coumarin moiety with other antibacterial pharmacophores may provide opportunities for the development of novel antibiotics. This review outlines the advances in coumarin-containing hybrids with antibacterial potential in the recent 5 years and the structure-activity relationships are also discussed. K E Y W O R D S antibacterial, coumarin, hybrid compounds, structure-activity relationships

show abstract

“…The NO-releasing properties of compounds 9a-c were assessed in phosphate buffer of pH 7.4 with Griess reagent [23]. As shown in Table 5, compounds 9a-c were found to release moderate amounts of NO compared to the sodium nitrite standard solution, which may explain that the desired action of NO is mediated systemically in the biological system [24].…”

Section: In Vitro Nitric Oxide Releasementioning

confidence: 99%

Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: multi-target compounds with dual antimicrobial and anti-inflammatory activities

et al. 2020

View full text Add to dashboard Cite

Three series of 2-(4-methylsulfonylphenyl) indole derivatives have been designed and synthesized. The synthesized compounds were assessed for their antimicrobial, COX inhibitory and anti-inflammatory activities. Compound 7g was identified to be the most potent antibacterial candidate against strains of MRSA, E. coli, K. pneumoniae, P. aeruginosa, and A. baumannii, respectively, with safe therapeutic dose. Compounds 7a-k, 8a-c, and 9a-c showed good antiinflammatory activity with excessive selectivity towards COX-2 in comparison with reference drugs indomethacin and celecoxib. Compounds 9a-c were found to release moderate amounts of NO to decrease the side effects associated with selective COX-2 inhibitors. A molecular modeling study for compounds 7b, 7h, and 7i into COX-2 active site was correlated with the results of in vitro COX-2 inhibition assays.

show abstract

Design and synthesis of new coumarin–chalcone/NO hybrids of potential biological activity

Cited by 30 publications

References 46 publications

Synthesis, CYP 450 evaluation, and docking simulation of novel 4‐aminopyridine and coumarin derivatives

Synthesis, CYP 450 evaluation, and docking simulation of novel 4‐aminopyridine and coumarin derivatives

Coumarin‐containing hybrids and their antibacterial activities

Synthesis and biological evaluation of 2-(4-methylsulfonyl phenyl) indole derivatives: multi-target compounds with dual antimicrobial and anti-inflammatory activities

Contact Info

Product

Resources

About