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dc.contributor.authorTawfeek, Hendawy N.
dc.contributor.authorAbdelmoez, Alshaimaa
dc.contributor.authorDahlous, Kholood A.
dc.contributor.authorYoussif, Bahaa G. M.
dc.contributor.authorBräse, Stefan
dc.contributor.authorRissanen, Kari
dc.contributor.authorNieger, Martin
dc.contributor.authorEl-Sheref, Essmat M.
dc.date.accessioned2024-08-07T09:02:05Z
dc.date.available2024-08-07T09:02:05Z
dc.date.issued2024
dc.identifier.citationTawfeek, H. N., Abdelmoez, A., Dahlous, K. A., Youssif, B. G. M., Bräse, S., Rissanen, K., Nieger, M., & El-Sheref, E. M. (2024). Convenient synthesis and X-ray determination of 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative activity. <i>RSC Advances</i>, <i>14</i>(25), 17866-17876. <a href="https://doi.org/10.1039/D4RA02531H" target="_blank">https://doi.org/10.1039/D4RA02531H</a>
dc.identifier.otherCONVID_221084178
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/96536
dc.description.abstractA new series of 1,3,4-thiadiazin-3-ium bromide derivatives 9a–g were prepared as a six-member ring by interactions between 4-substituted thiosemicarbazides 8a–e and α-halo ketones 2a,b. The reaction was conducted using hydrazine-NH2 and yielded a hexagonal shape. The structures of all obtained compounds have been verified using IR, NMR spectra, mass spectrometry, elemental analysis, and X-ray crystallography. The X-ray crystallographic analysis of compounds 9a and 9b has revealed that the salt is formed with the nitrogen atom N3 when the aromatic substituents 9a and 9d are present, but in the case of compounds 9b, 9c, 9e, 9f, and 9g with the aliphatic substituent, the salt is formed outside the ring. Compounds 9a–g were evaluated for antiproliferative activity as multitargeted inhibitors. Results revealed that targets 9a–g displayed good antiproliferative activity, with GI50 ranging from 38 nM to 66 nM against a panel of four cancer cell lines compared to the reference Erlotinib (GI50 = 33 nM). Compounds 9a, 9c, and 9d were the most potent antiproliferative derivatives, with GI50 values of 43, 38, and 47 nM, respectively. Compounds 9a, 9c, and 9d were evaluated for their inhibitory activity against EGFR, BRAFV600E, and VEGFR-2. The in vitro experiments demonstrated that the compounds being examined exhibit potent antiproliferative properties and have the potential to function as multitargeted inhibitors. In addition, the western blotting investigation demonstrated the inhibitory effects of 9c on EGFR, BRAFV600E, and VEGFR-2.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherRoyal Society of Chemistry (RSC)
dc.relation.ispartofseriesRSC Advances
dc.rightsCC BY-NC 4.0
dc.titleConvenient synthesis and X-ray determination of 2-amino-6H-1,3,4-thiadiazin-3-ium bromides endowed with antiproliferative activity
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202408075412
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange17866-17876
dc.relation.issn2046-2069
dc.relation.numberinseries25
dc.relation.volume14
dc.type.versionpublishedVersion
dc.rights.copyright© 2024 the Authors
dc.rights.accesslevelopenAccessfi
dc.subject.ysobioaktiiviset yhdisteet
dc.subject.ysoinhibiittorit
dc.subject.ysoheterosykliset yhdisteet
dc.subject.ysobromidit
dc.subject.ysosyöpäsolut
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p28433
jyx.subject.urihttp://www.yso.fi/onto/yso/p24325
jyx.subject.urihttp://www.yso.fi/onto/yso/p38837
jyx.subject.urihttp://www.yso.fi/onto/yso/p5460
jyx.subject.urihttp://www.yso.fi/onto/yso/p23898
dc.rights.urlhttps://creativecommons.org/licenses/by-nc/4.0/
dc.relation.doi10.1039/D4RA02531H
jyx.fundinginformationThis work was funded by the Researchers Supporting Project Number (RSP2024R388) at King Saud University, Riyadh, Saudi Arabia. The authors also acknowledge support from the KIT-Publication Fund of the Karlsruhe Institute of Technology.
dc.type.okmA1


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