Synthesis, biological evaluation and molecular docking studies of 8-(hetero)aryl caffeine derivatives

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dc.authoridKhan, Siraj/0000-0003-1948-452X
dc.authorwosidYaşar, Şeyma/ABI-8055-2020
dc.authorwosidRehman, Asim Ur/J-4207-2015
dc.contributor.authorKhan, Siraj
dc.contributor.authorBugday, Nesrin
dc.contributor.authorYasar, Seyma
dc.contributor.authorRehman, Asim Ur.
dc.contributor.authorUl Haq, Ihsan
dc.contributor.authorYasar, Sedat
dc.date.accessioned2024-08-04T20:54:28Z
dc.date.available2024-08-04T20:54:28Z
dc.date.issued2023
dc.departmentİnönü Üniversitesien_US
dc.description.abstractA series of 8-(hetero)aryl caffeine was synthesized by the C -H bond activation reaction using Pd-NHCs complexes as a catalyst. 8-(hetero)aryl caffeine derivatives were screened for their antioxidant, antimicro-bial, and enzyme inhibitory activities and in-silico studies. The 4a, 4b, 4e, 4f, 4 g, 4i, and 4n showed sig-nificant total antioxidant capacity (TAC) of 64.03, 50.87, 70.02, 98.14, 71.81, 45.48, and 44.28 & mu;g AAE/mg, respectively. The 4a, 4b, 4d, 4e, 6 h, 4i, 4j, 4k, and 4l were found active against Staphylococcus aureus at a minimum inhibitory concentration of 25, 12.5, 12.5, 12.5, 12.5, 6.25, 6.25, 6.25, and 6.25 & mu;g/ml, respec-tively. Some derivatives displayed activity against Escherichia coli, Bacillus subtilus, Klebsiella pneumonae, and Pseudomonas aeruginosa.A good activity was exhibited against Alternaria solani among five fungal strains. All the com-pounds (4a-4n) showed excellent protein kinase inhibitory activity except 4e, 4 g, and 4n. Addition-ally, 8-(hetero)aryl caffeine derivatives showed & alpha;-amylase inhibition potential (IC50 = 1.49 & PLUSMN; 0.317 to 7.44 & PLUSMN; 0.156 & mu;g/ml) compared to standard acarbose (IC50 = 4.34 & PLUSMN; 0.333 & mu;g/ml). The 4b, 4d, 4j, 4 m, and 4n compounds displayed good & alpha;-glucosidase inhibitory potential. Molecular modeling was done for protein kinase, & alpha;-amylase, and & alpha;-glucosidase. The results of these activities proved the caffeine deriva-tives to be bioactive.& COPY; 2023 Elsevier B.V. All rights reserved.en_US
dc.description.sponsorshipHigher Education Commission (HEC) of Pakistan [518-78015-2MD5-047 (50043709)]en_US
dc.description.sponsorshipThe authors would like to thank the Higher Education Commission (HEC) of Pakistan for financial support provided by the Indigenous PhD fellowship (PIN NO. 518-78015-2MD5-047 (50043709)) for SK.& nbsp;& nbsp;en_US
dc.identifier.doi10.1016/j.jorganchem.2023.122794
dc.identifier.issn0022-328X
dc.identifier.issn1872-8561
dc.identifier.scopus2-s2.0-85163173744en_US
dc.identifier.scopusqualityQ3en_US
dc.identifier.urihttps://doi.org/10.1016/j.jorganchem.2023.122794
dc.identifier.urihttps://hdl.handle.net/11616/101431
dc.identifier.volume997en_US
dc.identifier.wosWOS:001030784000001en_US
dc.identifier.wosqualityQ2en_US
dc.indekslendigikaynakWeb of Scienceen_US
dc.indekslendigikaynakScopusen_US
dc.language.isoenen_US
dc.publisherElsevier Science Saen_US
dc.relation.ispartofJournal of Organometallic Chemistryen_US
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanıen_US
dc.rightsinfo:eu-repo/semantics/closedAccessen_US
dc.subject8-(hetero)aryl xanthinesen_US
dc.subjectC -H bond activationen_US
dc.subjectBiological activitiesen_US
dc.subjectMolecular dockingen_US
dc.subjectStructure activity relationshipen_US
dc.titleSynthesis, biological evaluation and molecular docking studies of 8-(hetero)aryl caffeine derivativesen_US
dc.typeArticleen_US

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