A biochemistry‐oriented drug design: synthesis, anticancer activity, enzymes inhibition, molecular docking studies of novel 1,2,4-triazole derivatives

References

• Abidi, S. H., Bilwani, F., Ghias, K., & Abbas, F. (2018). Viral etiology of prostate cancer: Genetic alterations and immune response. A literature review. International Journal of Surgery (London, England), 52, 136–140. https://doi.org/10.1016/j.ijsu.2018.02.050
   PubMed Web of Science ®Google Scholar
• Akin, M., Günsel, A., Bilgiçli, A. T., Tüzün, B., Arabaci, G., Şaki, N., & Yarasir, M. N. (2020). The water-soluble peripheral substituted phthalocyanines as corrosion inhibitors for copper in 0.1 N HCl: Gravimetric, electrochemical, SEM-EDS, and quantum chemical calculations. Protection of Metals and Physical Chemistry of Surfaces, 56(3), 609–618. https://doi.org/10.1134/S207020512003003X
   Web of Science ®Google Scholar
• Aktas, A., Tuzun, B., Taskin, A. H., Sayin, K., & Ataseven, H. (2020). How do arbidol and its analogs inhibit the SARS-CoV-2? Bratislavske Lekarske Listy, 121(10), 705–711. https://doi.org/10.4149/BLL_2020_115
   PubMed Web of Science ®Google Scholar
• Al-Janabi, I. A. S., Yavuz, S. Ç., Köprü, S., Tapera, M., Kekeçmuhammed, H., Akkoç, S., Tüzün, B., Patat, Ş., & Sarıpınar, E. (2022). Antiproliferative activity and molecular docking studies of new 4-oxothiazolidin-5-ylidene acetate derivatives containing guanylhydrazone moiety. Journal of Molecular Structure, 1258, 132627. https://doi.org/10.1016/j.molstruc.2022.132627
   Web of Science ®Google Scholar
• Alici, E. H., Bilgiçli, A. T., Tüzün, B., Günsel, A., Arabaci, G., & Yarasir, M. N. (2022). Alkyl chain modified metalophthalocyanines with enhanced antioxidant-antimicrobial properties by doping Ag + and Pd2+ ions. Journal of Molecular Structure, 1257, 132634. https://doi.org/10.1016/j.molstruc.2022.132634
   Web of Science ®Google Scholar
• Barlak, N., Capik, O., Kilic, A., Sanli, F., Aytatli, A., Yazici, A., Karatas, E. A., Ortucu, S., & Karatas, O. F. (2021). MicroRNA‐145 transcriptionally regulates Semaphorin 3A expression in prostate cancer cells. Cell Biology International, 45(5), 1082–1090. https://doi.org/10.1002/cbin.11554
   PubMed Web of Science ®Google Scholar
• Bayrak, H., Demirbas, A., Karaoglu, S. A., & Demirbas, N. (2009). Synthesis of some new 1, 2, 4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities. European Journal of Medicinal Chemistry, 44(3), 1057–1066. https://doi.org/10.1016/j.ejmech.2008.06.019
   PubMed Web of Science ®Google Scholar
• Becke, A. D. (1992). Density‐functional thermochemistry. I. The effect of the exchange‐only gradient correction. The Journal of Chemical Physics, 96(3), 2155–2160. https://doi.org/10.1063/1.462066
   Web of Science ®Google Scholar
• Bilgicli, H. G., Kestane, A., Taslimi, P., Karabay, O., Bytyqi-Damoni, A., Zengin, M., & Gulcin, I. (2019). Novel eugenol bearing oxypropanolamines: Synthesis, characterization, antibacterial, antidiabetic, and anticholinergic potentials. Bioorganic Chemistry, 88, 102931. https://doi.org/10.1016/j.bioorg.2019.102931
   PubMed Web of Science ®Google Scholar
• Bilgiçli, A. T., Kandemir, T., Tüzün, B., Arıduru, R., Günsel, A., Abak, Ç., Yarasir, M. N., & Arabaci, G. (2021). Octa‐substituted Zinc (II), Cu (II), and Co (II) phthalocyanines with 1‐(4‐hydroxyphenyl) propane‐1‐one: Synthesis, sensitive protonation behaviors, Ag (I) induced H‐type aggregation properties, antibacterial–antioxidant activity, and molecular docking studies. Applied Organometallic Chemistry, 35(10), e6353. https://doi.org/10.1002/aoc.6353
   Web of Science ®Google Scholar
• Bilgicli, A. T., Bilgiçli, H. G., Günsel, A., Pişkin, H., Tüzün, B., Yarasir, M. N., & Zengin, M. (2020). The new ball-type zinc phthalocyanine with SS bridge; Synthesis, computational and photophysicochemical properties. Journal of Photochemistry and Photobiology A: Chemistry, 389, 112287. https://doi.org/10.1016/j.jphotochem.2019.112287
   Web of Science ®Google Scholar
• Bursal, E., Aras, A., Kılıç, Ö., Taslimi, P., Gören, A. C., & Gülçin, İ. (2019). Phytochemical content, antioxidant activity, and enzyme inhibition effect of Salvia eriophora Boiss. & Kotschy against acetylcholinesterase, α‐amylase, butyrylcholinesterase, and α‐glycosidase enzymes. Journal of Food Biochemistry, 43(3), e12776. https://doi.org/10.1111/jfbc.12776
   PubMed Web of Science ®Google Scholar
• Cheung, J., Gary, E. N., Shiomi, K., & Rosenberry, T. L. (2013). Structures of human acetylcholinesterase bound to dihydrotanshinone I and territrem B show peripheral site flexibility. ACS Medicinal Chemistry Letters, 4(11), 1091–1096. https://doi.org/10.1021/ml400304w
   PubMed Web of Science ®Google Scholar
• Chinnasamy, S., Selvaraj, G., Kaushik, A. C., Kaliamurthi, S., Chandrabose, S., Singh, S. K., Thirugnanasambandam, R., Gu, K., & Wei, D. Q. (2020). Molecular docking and molecular dynamics simulation studies to identify potent AURKA inhibitors: Assessing the performance of density functional theory, MM-GBSA and mass action kinetics calculations. Journal of Biomolecular Structure & Dynamics, 38(14), 4325–4335. https://doi.org/10.1080/07391102.2019.1674695
   PubMed Web of Science ®Google Scholar
• Dennington, R., Keith, T., & Millam, J. (2016). GaussView, version 6. Semichem Inc.
   Google Scholar
• DeVore, N. M., & Scott, E. E. (2012). Structures of cytochrome P450 17A1 with prostate cancer drugs abiraterone and TOK-001. Nature, 482(7383), 116–119. https://doi.org/10.1038/nature10743
   PubMed Web of Science ®Google Scholar
• El Faydy, M., Dahaieh, N., Ounine, K., Lakhrissi, B., Warad, I., Tüzün, B., & Zarrouk, A. (2022). Synthesis, identification, antibacterial activity, ADME/T and 1BNA-docking investigations of 8-quinolinol analogs bearing a benzimidazole moiety. Arabian Journal for Science and Engineering, 47(1), 497–510. https://doi.org/10.1007/s13369-021-05749-7
   Web of Science ®Google Scholar
• Ellman, G. L., Courtney, K. D., Andres, V., & Feather-Stone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7(2), 88–95. https://doi.org/10.1016/0006-2952(61)90145-9
   PubMed Web of Science ®Google Scholar
• Ezabadi, I. R., Camoutsis, C., Zoumpoulakis, P., Geronikaki, A., Soković, M., Glamočilija, J., & Ćirić, A. (2008). Sulfonamide-1, 2, 4-triazole derivatives as antifungal and antibacterial agents: Synthesis, biological evaluation, lipophilicity, and conformational studies. Bioorganic & Medicinal Chemistry, 16(3), 1150–1161. https://doi.org/10.1016/j.bmc.2007.10.082
   PubMed Web of Science ®Google Scholar
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., … Fox, D. (2009). J.W.R.L. J Gaussian 09, revision D.01. Gaussian Inc.
   Google Scholar
• Gao, Y., Wang, H., Wang, J., & Cheng, M. (2020). In silico studies on p21-activated kinase 4 inhibitors: Comprehensive application of 3D-QSAR analysis, molecular docking, molecular dynamics simulations, and MM-GBSA calculation. Journal of Biomolecular Structure & Dynamics, 38(14), 4119–4133. https://doi.org/10.1080/07391102.2019.1673823
   PubMed Web of Science ®Google Scholar
• Gedikli, M., Tuzun, B., Aktas, A., Sayin, K., & Ataseven, H. (2021). Are clarithromycin, azithromycin and their analogues effective in the treatment of COVID 19. Bratislavske Lekarske Listy, 122(2), 101–110. https://doi.org/10.4149/BLL_2021_015
   PubMed Web of Science ®Google Scholar
• Genç Bilgiçli, H., Bilgicli, A. T., Günsel, A., Tüzün, B., Ergön, D., Yarasir, M. N., & Zengin, M. (2020). Turn‐on fluorescent probe for Zn2+ ions based on thiazolidine derivative. Applied Organometallic Chemistry, 34(6), e5624. https://doi.org/10.1002/aoc.5624
   Web of Science ®Google Scholar
• Gheewala, T., Skwor, T., & Munirathinam, G. (2017). Photosensitizers in prostate cancer therapy. Oncotarget, 8(18), 30524–30538. https://doi.org/10.18632/oncotarget.15496
   PubMedGoogle Scholar
• Guillon, R., Giraud, F., Logé, C., Le Borgne, M., Picot, C., Pagniez, F., & Le Pape, P. (2009). Design of new antifungal agents: Synthesis and evaluation of 1-[(1H-indol-5-ylmethyl) amino]-2-phenyl-3-(1H-1, 2, 4-triazol-1-yl) propan-2-ols. Bioorganic & Medicinal Chemistry Letters, 19(20), 5833–5836. https://doi.org/10.1016/j.bmcl.2009.08.089
   PubMed Web of Science ®Google Scholar
• Günsel, A., Bilgiçli, A. T., Tüzün, B., Pişkin, H., Yarasir, M. N., & Gündüz, B. (2020). Optoelectronic parameters of peripherally tetra-substituted copper (ii) phthalocyanines and fabrication of a photoconductive diode for various conditions. New Journal of Chemistry, 44(2), 369–380. https://doi.org/10.1039/C9NJ05287A
   Web of Science ®Google Scholar
• Günsel, A., Bilgiçli, A. T., Pişkin, H., Tüzün, B., Delibaş, N. Ç., Yarasir, M. N., & Gündüz, B. (2019). Comparison of spectroscopic, electronic, theoretical, optical and surface morphological properties of functional manganese (III) phthalocyanine compounds for various conditions. Journal of Molecular Structure, 1193, 247–264. https://doi.org/10.1016/j.molstruc.2019.05.045
   Web of Science ®Google Scholar
• Günsel, A., Bilgiçli, A. T., Pişkin, H., Tüzün, B., Yarasir, M. N., & Gündüz, B. (2019). Synthesis of non-peripherally tetra-substituted copper (ii) phthalocyanines: Characterization, optical and surface properties, fabrication and photo-electrical properties of a photosensitive diode. Dalton Transactions (Cambridge, England: 2003), 48(39), 14839–14852. https://doi.org/10.1039/c9dt02868d
   PubMed Web of Science ®Google Scholar
• Hohenstein, E. G., Chill, S. T., & Sherrill, C. D. (2008). Assessment of the performance of the M05 − 2X and M06 − 2X exchange-correlation functionals for noncovalent interactions in biomolecules. Journal of Chemical Theory and Computation, 4(12), 1996–2000. https://doi.org/10.1021/ct800308k
   PubMed Web of Science ®Google Scholar
• Jiang, S., Mo, C., Guo, S., Zhuang, J., Huang, B., & Mao, X. (2019). Human bone marrow mesenchymal stem cells-derived microRNA-205-containing exosomes impede the progression of prostate cancer through suppression of RHPN2. Journal of Experimental & Clinical Cancer Research, 38(1), 1–16. https://doi.org/10.1186/s13046-019-1488-1
   PubMed Web of Science ®Google Scholar
• Jorgensen, W. J., & Duffy, E. M. (2002). Prediction of drug solubility from structure. Advanced Drug Delivery Reviews, 54(3), 355–366. https://doi.org/10.1016/s0169-409x(02)00008-x
   PubMed Web of Science ®Google Scholar
• Ivansky, V. I. (1978).Chemistry of Heterocyclic Compounds (pp. 175-177) [in Russian]. Moscow: Vysshaya Shkola.
   Google Scholar
• Khalilov, A. N., Tüzün, B., Taslimi, P., Tas, A., Tuncbilek, Z., & Cakmak, N. K. (2021). Cytotoxic effect, spectroscopy, DFT, enzyme inhibition, and moleculer docking studies of some novel mesitylaminopropanols: Antidiabetic and anticholinergics and anticancer potentials. Journal of Molecular Liquids, 344, 117761. https://doi.org/10.1016/j.molliq.2021.117761
   Web of Science ®Google Scholar
• Khilkovets, A. V. (2021). Investigation of physical and chemical properties of new derivatives of 5-(thiophene-3-ylmethyl)-4R-1,2,4-triazole-3-thiols. Current Issues in Pharmacy and Medicine: Science and Practice, 14(2), 152–156. https://doi.org/10.14739/2409-2932.2021.2.232334
   Google Scholar
• Košak, U., Brus, B., Knez, D., Žakelj, S., Trontelj, J., Pišlar, A., Šink, R., Jukič, M., Živin, M., Podkowa, A., Nachon, F., Brazzolotto, X., Stojan, J., Kos, J., Coquelle, N., Sałat, K., Colletier, J.-P., & Gobec, S. (2018). The magic of crystal structure-based inhibitor optimization: Development of a butyrylcholinesterase inhibitor with picomolar affinity and in vivo activity. Journal of Medicinal Chemistry, 61(1), 119–139. https://doi.org/10.1021/acs.jmedchem.7b01086
   PubMed Web of Science ®Google Scholar
• Koçyiğit, Ü. M., Doğan, M., Muğlu, H., Taslimi, P., Tüzün, B., Yakan, H., Bal, H., Güzel, E., & Gülçin, İ. (2022). Determination of biological studies and molecular docking calculations of isatin-thiosemicarbazone hybrid compounds. Journal of Molecular Structure, 1264, 133249. https://doi.org/10.1016/j.molstruc.2022.133249
   Web of Science ®Google Scholar
• Kökbudak, Z., Akkoç, S., Karataş, H., Tüzün, B., & Aslan, G. (2022). In Silico and In Vitro Antiproliferative Activity Assessment of New Schiff Bases. ChemistrySelect, 7(3), e202103679. https://doi.org/10.1002/slct.202103679
   Web of Science ®Google Scholar
• Lakhrissi, Y., Rbaa, M., Tuzun, B., Hichar, A., Anouar, E. H., Ounine, K., Almalki, F., Hadda, T. B., Zarrouk, A., & Lakhrissi, B. (2022). Synthesis, structural confirmation, antibacterial properties and bio-informatics computational analyses of new pyrrole based on 8-hydroxyquinoline. Journal of Molecular Structure, 1259, 132683. https://doi.org/10.1016/j.molstruc.2022.132683
   Web of Science ®Google Scholar
• Lipinski, C. A. (2004). Lead-and drug-like compounds: The rule-of-five revolution. Drug Discovery Today. Technologies, 1(4), 337–341. https://doi.org/10.1016/j.ddtec.2004.11.007
   PubMedGoogle Scholar
• Lipinski, C. A., Lombardo, F., Dominy, B. W., & Feeney, P. J. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Advanced Drug Delivery Reviews, 23(1–3), 3–25. https://doi.org/10.1016/S0169-409X(96)00423-1
   Web of Science ®Google Scholar
• Liu, H. T., Fang, L., Cheng, Y. X., & Sun, Q. (2016). LncRNA PVT1 regulates prostate cancer cell growth by inducing the methylation of miR‐146a. Cancer Medicine, 5(12), 3512–3519. https://doi.org/10.1002/cam4.900
   PubMed Web of Science ®Google Scholar
• Ozgun, D. O., Yamali, C., Gul, H. I., Taslimi, P., Gulcin, I., Yanik, T., & Supuran, C. T. (2016). Inhibitory effects of isatin Mannich bases on carbonic anhydrases, acetylcholinesterase, and butyrylcholinesterase. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(6), 1498–1501. https://doi.org/10.3109/14756366.2016.1149479
   PubMed Web of Science ®Google Scholar
• Ökten, S., Ekiz, M., Koçyiğit, Ü. M., Tutar, A., Çelik, İ., Akkurt, M., Gökalp, F., Taslimi, P., & Gülçin, İ. (2019). Synthesis, characterization, crystal structures, theoretical calculations and biological evaluations of novel substituted tacrine derivatives as cholinesterase and carbonic anhydrase enzymes inhibitors. Journal of Molecular Structure, 1175, 906–915. https://doi.org/10.1016/j.molstruc.2018.08.063
   Web of Science ®Google Scholar
• Parchenko, V. V. (2014). [ Syntez, peretvorennia, fizyko-khimichni ta biolohichni vlastyvosti v riadi 5-furylzamishchenykh 1, 2, 4-triazol-3-tioniv (Dis… dokt. farm. nauk) ]. [Synthesis, transformation, physico-chemical and biological properties in the number of 5-furylsubstituted 1, 2, 4-triazole-3-thiones][doctoral dissertation]. Zaporizhzhia.[in Ukrainian].
   Google Scholar
• Pashaei, E., Pashaei, E., Ahmady, M., Ozen, M., & Aydin, N. (2017). Meta-analysis of miRNA expression profiles for prostate cancer recurrence following radical prostatectomy. PLoS One, 12(6), e0179543. https://doi.org/10.1371/journal.pone.0179543
   PubMed Web of Science ®Google Scholar
• Pernar, C. H., Ebot, E. M., Wilson, K. M., & Mucci, L. A. (2018). The epidemiology of prostate cancer. Cold Spring Harbor Perspectives in Medicine, 8(12), a030361. https://doi.org/10.1101/cshperspect.a030361
   PubMed Web of Science ®Google Scholar
• Poustforoosh, A., Hashemipour, H., Tüzün, B., Pardakhty, A., Mehrabani, M., & Nematollahi, M. H. (2021). Evaluation of potential anti-RNA-dependent RNA polymerase (RdRP) drugs against the newly emerged model of COVID-19 RdRP using computational methods. Biophysical Chemistry, 272, 106564. https://doi.org/10.1016/j.bpc.2021.106564
   PubMed Web of Science ®Google Scholar
• Rbaa, M., Haida, S., Tuzun, B., Hichar, A., Hassane, A. E., Kribii, A., Lakhrissi, Y., Hadda, T. B., Zarrouk, A., Lakhrissi, B., & Berdimurodov, E. (2022). Synthesis, characterization and bioactivity of novel 8-hydroxyquinoline derivatives: Experimental, molecular docking, DFT and POM analyses. Journal of Molecular Structure, 1258, 132688. https://doi.org/10.1016/j.molstruc.2022.132688
   Web of Science ®Google Scholar
• Riaz, M. T., Yaqub, M., Shafiq, Z., Ashraf, A., Khalid, M., Taslimi, P., Tas, R., Tuzun, B., & Gulçin, İ. (2021). Synthesis, biological activity and docking calculations of bis-naphthoquinone derivatives from lawsone. Bioorganic Chemistry, 114, 105069. https://doi.org/10.1016/j.bioorg.2021.105069
   PubMed Web of Science ®Google Scholar
• Rezaeivala, M., Karimi, S., Sayin, K., & Tüzün, B. (2022a). Experimental and theoretical investigation of corrosion inhibition effect of two piperazine-based ligands on carbon steel in acidic media. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 641, 128538. https://doi.org/10.1016/j.colsurfa.2022.128538
   Web of Science ®Google Scholar
• Rezaeivala, M., Karimi, S., Tuzun, B., & Sayin, K. (2022b). Anti-corrosion behavior of 2-((3-(2-morpholino ethylamino)-N3-((pyridine-2-yl) methyl) propylimino) methyl) pyridine and its reduced form on Carbon Steel in Hydrochloric Acid solution: Experimental and theoretical studies. Thin Solid Films, 741, 139036. https://doi.org/10.1016/j.tsf.2021.139036
   Web of Science ®Google Scholar
• Rosenfeld, L., Sananes, A., Zur, Y., Cohen, S., Dhara, K., Gelkop, S., Ben Zeev, E., Shahar, A., Lobel, L., Akabayov, B., Arbely, E., & Papo, N. (2020). Nanobodies targeting prostate-specific membrane antigen for the imaging and therapy of prostate cancer. Journal of Medicinal Chemistry, 63(14), 7601–7615. https://doi.org/10.1021/acs.jmedchem.0c00418
   PubMed Web of Science ®Google Scholar
• Sarigol, D., Uzgoren-Baran, A., Tel, B. C., Somuncuoglu, E. I., Kazkayasi, I., Ozadali-Sari, K., Unsal-Tan, O., Okay, G., Ertan, M., & Tozkoparan, B. (2015). Novel thiazolo [3, 2-b]-1, 2, 4-triazoles derived from naproxen with analgesic/anti-inflammatory properties: Synthesis, biological evaluation and molecular modeling studies. Bioorganic & Medicinal Chemistry, 23(10), 2518–2528. https://doi.org/10.1016/j.bmc.2015.03.049
   PubMed Web of Science ®Google Scholar
• Sert‐Ozgur, S., Tel, B. C., Somuncuoglu, E. I., Kazkayasi, I., Ertan, M., & Tozkoparan, B. (2017). Design and Synthesis of 1, 2, 4‐Triazolo [3, 2‐b]‐1, 3, 5‐thiadiazine Derivatives as a Novel Template for Analgesic/Anti‐Inflammatory Activity. Archiv Der Pharmazie, 350(7), e1700052. https://doi.org/10.1002/ardp.201700052
   Web of Science ®Google Scholar
• Schrödinger Release 2021-3. (2021a). Maestro. Schrödinger, LLC.
   Google Scholar
• Schrödinger Release 2021-3. (2021b). Protein Preparation Wizard; Epik, Schrödinger, LLC, New York, NY, 2016; Impact, Schrödinger, LLC, New York, NY, 2016; Prime. Schrödinger LLC.
   Google Scholar
• Schrödinger Release 2021-3. (2021c). LigPrep. Schrödinger, LLC.
   Google Scholar
• Schrödinger Release 2021-3. (2021d). QikProp. Schrödinger, LLC.
   Google Scholar
• Shekhar, M. S., Venkatachalam, T., Sharma, C. S., Pratap Singh, H., Kalra, S., & Kumar, N. (2019). Computational investigation of binding mechanism of substituted pyrazinones targeting corticotropin releasing factor-1 receptor deliberated for anti-depressant drug design. Journal of Biomolecular Structure & Dynamics, 37(12), 3226–3244. https://doi.org/10.1080/07391102.2018.1513379
   PubMed Web of Science ®Google Scholar
• Sujayev, A., Garibov, E., Taslimi, P., Gulçin, İ., Gojayeva, S., Farzaliyev, V., Alwasel, S. H., & Supuran, C. T. (2016). Synthesis of some tetrahydropyrimidine-5-carboxylates, determination of their metal chelating effects and inhibition profiles against acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase. Journal of Enzyme Inhibition and Medicinal Chemistry, 31(6), 1531–1539. https://doi.org/10.3109/14756366.2016.1156104
   PubMed Web of Science ®Google Scholar
• Sur, S., Steele, R., Shi, X., & Ray, R. B. (2019). miRNA-29b inhibits prostate tumor growth and induces apoptosis by increasing bim expression. Cells, 8(11), 1455. https://doi.org/10.3390/cells8111455
   PubMed Web of Science ®Google Scholar
• Taslimi, P., & Gulçin, İ. (2018). Antioxidant and anticholinergic properties of olivetol. Journal of Food Biochemistry, 42(3), e12516. https://doi.org/10.1111/jfbc.12516
   Web of Science ®Google Scholar
• Tozkoparan, B., Küpeli, E., Yeşilada, E., Işik, S., Ozalp, M., & Ertan, M. (2005). Synthesis and evaluation of analgesic/anti-inflammatory and antimicrobial activities of 3-substituted-1, 2, 4-triazole-5-thiones. Arzneimittel-Forschung, 55(9), 533–540. https://doi.org/10.1055/s-0031-1296901
   PubMed Web of Science ®Google Scholar
• Tozkoparan, B., Aytaç, S. P., Gürsoy, Ş., & Aktay, G. (2012). Design and synthesis of some thiazolotriazolyl esters as anti-inflammatory and analgesic agents. Medicinal Chemistry Research, 21(2), 192–201. https://doi.org/10.1007/s00044-010-9508-x
   Web of Science ®Google Scholar
• Tozkoparan, B., Aytac, S. P., Gursoy, S., Gunal, S., & Aktay, G. (2012). Novel 1, 2, 4-triazolo [3, 4-b]-1, 3, 4-thiadiazole derivatives as dual analgesic/anti-inflammatory and antimicrobial agents. Letters in Drug Design & Discovery, 9(2), 204–212. https://doi.org/10.2174/157018012799079626
   Web of Science ®Google Scholar
• Türkan, F., Taslimi, P., Abdalrazaq, S. M., Aras, A., Erden, Y., Celebioglu, H. U., Tuzun, B., Ağırtaş, M. S., & Gülçin, İ. (2021). Determination of anticancer properties and inhibitory effects of some metabolic enzymes including acetylcholinesterase, butyrylcholinesterase, alpha-glycosidase of some compounds with molecular docking study. Journal of Biomolecular Structure & Dynamics, 39(10), 3693–3702. https://doi.org/10.1080/07391102.2020.1768901
   PubMed Web of Science ®Google Scholar
• Uzgören-Baran, A., Tel, B. C., Sarıgöl, D., Oztürk, E. İ., Kazkayası, I., Okay, G., Ertan, M., & Tozkoparan, B. (2012). Thiazolo [3, 2-b]-1, 2, 4-triazole-5 (6H)-one substituted with ibuprofen: Novel non-steroidal anti-inflammatory agents with favorable gastrointestinal tolerance. European Journal of Medicinal Chemistry, 57, 398–406. https://doi.org/10.1016/j.ejmech.2012.07.009
   PubMed Web of Science ®Google Scholar
• Xing, Z., Li, S., Liu, Z., Zhang, C., Meng, M., & Bai, Z. (2020). The long non-coding RNA LINC00473 contributes to cell proliferation via JAK-STAT3 signaling pathway by regulating miR-195-5p/SEPT2 axis in prostate cancer. Bioscience Reports, 40(9). https://doi.org/10.1042/BSR20191850
   Google Scholar
• Vautherin, D., & Brink, D. T. (1972). Hartree-Fock calculations with Skyrme’s interaction. I. Spherical nuclei. Physical Review C, 5(3), 626–647. https://doi.org/10.1103/PhysRevC.5.626
   Web of Science ®Google Scholar
• Villa-Pulgarin, J. A., Salamanca, C. H., Oñate-Garzón, J., & Varela-M, R. E. (2020). Antitumor Activity In Vitro Provided by N-Alkyl-Nitroimidazole Compounds. Journal: The Open Medicinal Chemistry Journal, 14(1), 45–48.
   Google Scholar
• Wang, M., Wang, Y., Kong, D., Jiang, H., Wang, J., & Cheng, M. (2018). In silico exploration of aryl sulfonamide analogs as voltage-gated sodium channel 1.7 inhibitors by using 3D-QSAR, molecular docking study, and molecular dynamics simulations. Computational Biology and Chemistry, 77, 214–225. https://doi.org/10.1016/j.compbiolchem.2018.10.009
   PubMed Web of Science ®Google Scholar
• Yan, H. B., Zhang, Y., Cen, J. M., Wang, X., Gan, B. L., Huang, J. C., Li, J. Y., Song, Q. H., Li, S. H., & Chen, G. (2018). Expression of microRNA-99a-3p in prostate cancer based on bioinformatics data and meta-analysis of a literature review of 965 cases. Medical Science Monitor: International Medical Journal of Experimental and Clinical Research, 24, 4807–4822. https://doi.org/10.12659/MSM.908057
   PubMed Web of Science ®Google Scholar
• Yavuz, S. Ç., Akkoç, S., Tüzün, B., Şahin, O., & Saripinar, E. (2021). Efficient synthesis and molecular docking studies of new pyrimidine-chromeno hybrid derivatives as potential antiproliferative agents. Synthetic Communications, 51(14), 2135–2159. https://doi.org/10.1080/00397911.2021.1922920
   Web of Science ®Google Scholar
• Zazharskiy, V., Zazharskiy, V., Zazharskyi, V., Zazharskyi, V., Zazharskiy, V., Zazharskyi, V., … Zazharska, N. N. (2020). Physicochemical properties of new s-derivatives of 5-(5-bromofuran-2-yl)-4-methyl-1, 2, 4-triazol-3-thiols. Voprosy Khimii i Khimicheskoi Tekhnologii, 6, 50–58. https://doi.org/10.32434/0321-4095-2020-133-6-50-58
   Google Scholar