28354-25-8Relevant articles and documents
New pyrimidine and pyrazole-based compounds as potential EGFR inhibitors: Synthesis, anticancer, antimicrobial evaluation and computational studies
Alamshany, Zahra M.,Anwar, Manal M.,Gad-Elkareem, Mohamed A. M.,Nossier, Eman S.,Othman, Ismail M. M.,Tashkandi, Nada Y.
, (2021)
This study was focused on the synthesis of new pyrimidines 4a,b, 5a,b and pyrazoles 6a, b as ATP mimicking tyrosine kinase inhibitors of the epidermal growth factor receptor (EGFR). The new compounds were assessed as cytotoxic candidates against human breast cancer cells (MCF-7) and hepatocellular carcinoma cells (HepG-2). All the new compounds appeared as more potent cytotoxic agents than erlotinib, while only compound 4a exhibited more potency than 5-flourouracil and 4b analogue was equipotent to it. Accordingly, the kinase suppression effect of 4a and 4b was further evaluated against EGFRWT, EGFRL858R and EGFRT790M. Both pyrimidine analogues 4a and 4b displayed outstanding inhibitory activity against EGFRWT and its two mutated isoforms EGFRL858R and EGFRT790M in comparing to erlotinib and osimertinib as reference drugs. Additionally, all the new analogues were subjected to antimicrobial assay. Interestingly, both 4a and 4b represented the most promising activity of wide spectrum antimicrobial effect against the examined microbes in comparison to gentamycin and ketoconazole as standard drugs. Moreover, docking results proved the good binding interactions of the compounds 4a and 4b with EGFRWT and EGFRT790M which were in accordance with the results of the in vitro enzyme assay. Additional in silico ADMET studies were performed for the new derivatives which represented their good oral absorption, good drug-likeness properties and low toxicity risks in human.
Anionic N-heterocyclic carbenes derived from sydnone imines such as molsidomine. Trapping reactions with selenium, palladium, and gold
Freese, Tyll,Lücke, Ana-Luiza,Schmidt, Catharina A.S.,Polamo, Mika,Nieger, Martin,Namyslo, Jan C.,Schmidt, Andreas
, p. 5350 - 5357 (2017/08/11)
The sydnone imines Molsidomine and 5-(benzoylimino)-3-(2-methoxyphenyl)-1,2,3-oxadiazolium-2-ide gave anionic N-heterocyclic carbenes on deprotonation at C4 which were trapped as methylated selenium adducts, gold complexes (X-ray analysis) as well as palladium complexes (X-ray analysis). The 13C NMR resonance frequencies of the carbene carbon atom are extremely shifted upfield and appear at δ = 142.1 ppm (Molsidomine carbene) and δ = 159.8 ppm (sydnone imine carbene). The Pd complexes were applied as catalysts in Suzuki-Miyaura and Sonogashira-Hagihara cross-coupling reactions.
Design, synthesis and antioxidant properties of ovothiol-derived 4-mercaptoimidazoles
Zoete, Vincent,Bailly, Fabrice,Catteau, Jean-Pierre,Bernier, Jean-Luc
, p. 2983 - 2988 (2007/10/03)
Fourteen 4-mercaptoimidazoles derived from the naturally occurring family of antioxidants, the ovothiols, have been synthesized by cyclization of thioamides with trimethylsilyl trifluoromethane-sulfonate (triflate). These compounds have been assayed for their radical-scavenging activity.
