Functionalized p-cymene and pyrazine derivatives: Physicochemical, ADMT, drug-likeness, and DFT studies

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dc.contributor.authorSerdaroglu, Goncagul
dc.date.accessioned2025-05-04T16:47:14Z
dc.date.available2025-05-04T16:47:14Z
dc.date.issued2025
dc.departmentSivas Cumhuriyet Üniversitesi
dc.description.abstractThe p-cymene and pyrazine derivatives functionalized with the hydroxy and methoxy group(s) were under the focus to explore the electronic structural properties, which would play a critical role in the biochemical reactivity features via performing systematic computational analyses. The DFT computations of the data set were performed by B3LYP/6-311 G* * level to predict the structural and electronic properties as well as the physicochemical values. The physicochemical properties such as lipophilicity and water solubility features were determined because these values should be in balance with each other in early-stage-drug-design research. The averaged lipophilicity of the p-cymene and pyrazine derivatives were calculated as CYM3 (2.39)< CYM1 (2.82)< CYM4 (3.11)< CYM2 (3.21)< CYM (3.50) and PYZ3 (1.22)< PYZ (1.28)< PYZ1 (1.40)< PYZ2 (1.79)< PYZ4 (2.00), respectively. According to the ESOL approach, the water solubility (mg/mL)x10(-2) values of the p-cymene and pyrazine compounds were changed in the following orders of CYM3 (15.6)> CYM4 (10.2)> CYM1 (7.40)>CYM2 (5.16)> CYM (3.12) and PYZ (512)> PYZ1 (170)> PYZ3 (166)> PYZ2 (118)> PYZ4 (77.3), respectively. The ADMT properties of the data set were dealt with in detail to estimate the structural advantage or disadvantage because the possible side effects on human-health and the environment have to be considered in designing the novel agent in addition to the possible potencies. All compounds would be promising agents in terms of the Caco-2 and MDCK penetration and Pgp-inhibition potencies. According to the IGC(50), LC50FM, and LC50DM results, the p-cymene compounds could have lower (or no) risk than the glyphosate and pyrazine derivatives like being for BCF scores. The FMO analyses were performed to estimate the possible reactive region for nucleophilic or electrophilic attacks.
dc.description.sponsorshipScientific Research Projects Department of Sivas Cumhuriyet University [EGT-2023-098]
dc.description.sponsorshipAll calculations have been carried out at TUBITAK ULAKBIM, High Performance and Grid Computing Center (TR-Grid e -Infrastructure). The author thanks to Scientific Research Projects Department of Sivas Cumhuriyet University (Project No: EGT-2023-098).
dc.identifier.doi10.1016/j.compbiolchem.2025.108434
dc.identifier.issn1476-9271
dc.identifier.issn1476-928X
dc.identifier.pmid40158239
dc.identifier.scopus2-s2.0-105001350959
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.compbiolchem.2025.108434
dc.identifier.urihttps://hdl.handle.net/20.500.12418/35544
dc.identifier.volume117
dc.identifier.wosWOS:001459103900001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.indekslendigikaynakPubMed
dc.institutionauthorSerdaroglu, Goncagul
dc.language.isoen
dc.publisherElsevier Sci Ltd
dc.relation.ispartofComputational Biology and Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250504
dc.subjectP-cymene
dc.subjectPyrazine
dc.subjectADMT
dc.subjectDrug-likeness
dc.subjectAnd DFT computations
dc.titleFunctionalized p-cymene and pyrazine derivatives: Physicochemical, ADMT, drug-likeness, and DFT studies
dc.typeArticle

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