WoS İndeksli Yayınlar Koleksiyonu
Permanent URI for this collectionhttps://hdl.handle.net/20.500.14627/6
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Article Synthesis, Experimental and Quantum Mechanical Investigation of the Crystal Structures of Two Triazolyl-Indole Compounds, along with the Evaluation of Their Antioxidant Activity(Elsevier, 2026) Pınar, Deniz; Kurt-Şirin, Özlem; Ulusoy-Güzeldemirci, Nuray; Dincel, Efe Doğukan; Karayel, Arzu; Kuran, Ebru DidemIn this study, two 1,2,4-triazolyl-indole compounds, 5-(1H-indol-3-yl)-4-propyl-2,4 dihydro-3H-1,2,4-triazole-3-thione (3a) and 5-(1H-indol-3-yl)-4-butyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (3b), were synthesized and the structures of these compounds were determined by X-ray diffraction method. These two compounds crystallize in the orthorhombic space groups, Pbca. The structures have been determined by direct methods and refined to R, 0.0459 (3a) and 0.0714 (3b). The molecular and crystal structures are stabilized by two intermolecular hydrogen bond for both molecules. The triazole parts of the molecules are almost perpendicular to propyl and butyl groups. NMR studies was also performed to enhance comprehension of the molecular structure of the compounds. The most stable states of the structures, as determined by both DFT analysis and experimental realizations (X-ray, NMR and FT-IR), are the thione form. Although the thione forms are thermodynamically more stable than the thiol forms (Delta H degrees approximate to-15 kcal/mol), they display higher chemical reactivity, as reflected by their smaller HOMO-LUMO energy gaps (Delta E = 4.374 eV for 3a and 4.377 eV for 3b). In addition, the antioxidant activities of both compounds were evaluated using ABTS, DPPH, and FRAP assays. Although both (3a) and (3b) exhibited measurable radical scavenging and reducing power, their antioxidant capacities were found to be lower than that of the reference compound quercetin.Article Design and Synthesis of Thiosemicarbazides and 1,2,4-Triazoles Derived From Ibuprofen as Potential Metap (Type II) Inhibitors(Elsevier Ireland Ltd, 2025) Yilmaz, Ozgur; Biliz, Yagmur; Ayan, Sumeyra; Cevik, Ozge; Karahasanoglu, Mufide; Cotuker, Reyhan; Kucukguzel, S. GunizIn the present study, a range of novel thiosemicarbazides 4a-i and 1,2,4-triazoles 5a-i derived from ibuprofen, were synthesized. Structural elucidation of these synthesized compounds was performed utilizing a variety of spectroscopic methods, including FTIR, 1H NMR, 13C NMR and HR-MS. The synthesized compounds were tested for cytotoxicity in five different cancer cell lines (cervical cancer (HeLa), human breast cancer (MCF-7), human gastric adenocarcinoma (MKN-45), human metastatic prostate cancer (PC3) and human glioblastoma (U87)). The compounds were compared with healthy cells (NIH-3T3) and the most effective compounds were determined by means of the selectivity index. Thiosemicarbazides derived form ibuprofen 4i and 4d showed anticancer activity, while 1,2,4-triazoles derived form ibuprofen 5b, 5c, 5d, 5e, 5h, 5g showed anticancer activity in HeLa, MCF-7, MKN-45, PC3 and U87 cells. To test the stability of the protein-drug complexes all 18 compounds 4a-i and 5a-i were docked into the active site of the MetAP2 enzyme In general, computational inhibition constants values were correlated with the experimental values. The dynamic behavior of MetAP2-inhibitor complexes was analyzed using all atoms Molecular Dynamic (MD) simulations for 200 ns duration. MD revealed that the drugs bind in the active center of MetAP2 with stable RMSD and RMSF. In conclusion, in-silico results and in-vitro studies suggests that thiosemicarbazides and 1,2,4-triazoles derived from ibuprofen may be novel anticancer drug candidates for treating cervical, breast, prostate, gastric and glioblastoma. Compounds provided induction of apoptotic proteins in the cell by inhibiting MetAP2 enzyme. Furthermore, the potential antioxidant activities of the compounds were evaluated using the 2,2-Diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay. Among the compounds tested, 4a, 4b, 4e, 4f, 4h, and 4i exhibited values closely resembling the DPPH activity of the standards.