Design, spectroscopic characterization, in silico and in vitro cytotoxic activity assessment of newly synthesized thymol Schiff base derivatives

References

• Aertgeerts, K., Skene, R., Yano, J., Sang, B.-C., Zou, H., Snell, G., Jennings, A., Iwamoto, K., Habuka, N., Hirokawa, A., Ishikawa, T., Tanaka, T., Miki, H., Ohta, Y., & Sogabe, S. (2011). Structural analysis of the mechanism of inhibition and allosteric activation of the kinase domain of HER2 protein. The Journal of Biological Chemistry, 286(21), 18756–18765. https://doi.org/10.1074/jbc.M110.206193
   PubMed Web of Science ®Google Scholar
• Akkoç, S., Gök, Y., İlhan, İ. Ö., & Kayser, V. (2016). N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: Synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions. Beilstein Journal of Organic Chemistry, 12, 81–88. https://doi.org/10.3762/bjoc.12.9
   PubMed Web of Science ®Google Scholar
• Alam, M. M., Malebari, A. M., Nazreen, S., Neamatallah, T., Almalki, A. S. A., Elhenawy, A. A., Obaid, R. J., & Alsharif, M. A. (2021). Design, synthesis and molecular docking studies of thymol based 1,2,3-triazole hybrids as thymidylate synthase inhibitors and apoptosis inducers against breast cancer cells. Bioorganic & Medicinal Chemistry, 38, 116136. https://doi.org/10.1016/j.bmc.2021.116136
   PubMed Web of Science ®Google Scholar
• Almalki, A. S. A., Nazreen, S., Malebari, A. M., Ali, N. M., Elhenawy, A. A., Alghamdi, A. A. A., Ahmad, A., Alfaifi, S. Y. M., Alsharif, M. A., & Alam, M. M. (2021). Synthesis and biological evaluation of 1,2,3-triazole tethered thymol-1,3,4-oxadiazole derivatives as anticancer and antimicrobial agents. Pharmaceuticals, 14(9), 866. https://doi.org/10.3390/ph14090866
   Web of Science ®Google Scholar
• Başaran, E. (2021). Some aryl sulfonyl ester-based heterocyclic Schiff bases: Synthesis, structure elucidation and antioxidant activity. Iğdır Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 11(4), 2967–2978. https://doi.org/10.21597/jist.963129
   Google Scholar
• Başaran, E., Çakmak, R., Akkoç, S., & Kaya, S. (2022a). Combined experimental and theoretical analyses on design, synthesis, characterization, and in vitro cytotoxic activity evaluation of some novel imino derivatives containing pyrazolone ring. Journal of Molecular Structure. 1265, 133427. https://doi.org/10.1016/j.molstruc.2022.133427
   Web of Science ®Google Scholar
• Başaran, E., Çakmak, R., Çinar, E., & Cevik, O. (2022b). Some heterocyclic hydrazone compounds: Synthesis, spectral characterization and anticancer activity study. Cumhuriyet Science Journal, 43(3), 437–442. https://doi.org/10.17776/csj.1099217
   Google Scholar
• Başaran, E., Gamze Sogukomerogullari, H., Cakmak, R., Akkoc, S., Taskin-Tok, T., & Köse, A. (2022c). Novel chiral Schiff base Palladium (II), Nickel (II), Copper (II) and Iron (II) complexes: Synthesis, characterization, anticancer activity and molecular docking studies. Bioorganic Chemistry, 129, 106176. https://doi.org/10.1016/j.bioorg.2022.106176
   PubMed Web of Science ®Google Scholar
• Başaran, E. (2023a). Schiff base derivatives based on ampyrone as promising acetylcholinesterase inhibitors: Synthesis, spectral characterization, biological activity, and SwissADME predictions. Russian Journal of Bioorganic Chemistry. 49, 114–126. https://doi.org/10.1134/S1068162023010065
   Web of Science ®Google Scholar
• Başaran, E. (2023b). Synthesis, antioxidant, and anticholinesterase activities of novel N-arylsulfonyl hydrazones bearing sulfonate ester scaffold. Journal of the Chinese Chemical Society, 70(7), 1580–1590. https://doi.org/10.1002/jccs.202300151
   Web of Science ®Google Scholar
• Bruncko, M., Oost, T. K., Belli, B. A., Ding, H., Joseph, M. K., Kunzer, A., Martineau, D., McClellan, W. J., Mitten, M., Ng, S.-C., Nimmer, P. M., Oltersdorf, T., Park, C.-M., Petros, A. M., Shoemaker, A. R., Song, X., Wang, X., Wendt, M. D., Zhang, H., … Elmore, S. W. (2007). Studies leading to potent, dual inhibitors of Bcl-2 and Bcl-xL. Journal of Medicinal Chemistry, 50(4), 641–662. https://doi.org/10.1021/jm061152t
   PubMed Web of Science ®Google Scholar
• Cui, Z., Li, X., & Nishida, Y. (2014). Synthesis and bioactivity of novel carvacrol and thymol derivatives containing 5-phenyl-2-furan. Letters in Drug Design & Discovery, 11(7), 877–885. https://doi.org/10.2174/1570180811666140220005252
   Web of Science ®Google Scholar
• Deo, S. V. S., Sharma, J., & Kumar, S. (2022). GLOBOCAN 2020 report on global cancer burden: Challenges and opportunities for surgical oncologists. Annals of Surgical Oncology, 29(11), 6497–6500. https://doi.org/10.1245/s10434-022-12151-6
   PubMed Web of Science ®Google Scholar
• Esmer, Y. İ., Çınar, E., & Başaran, E. (2022). Design, docking, synthesis and biological evaluation of novel nicotinohydrazone derivatives as potential butyrylcholinesterase enzyme inhibitor. ChemistrySelect, 7(33), e202202771. https://doi.org/10.1002/slct.202202771
   Web of Science ®Google Scholar
• Ferlay, J., Colombet, M., Soerjomataram, I., Mathers, C., Parkin, D. M., Piñeros, M., Znaor, A., & Bray, F. (2019). Estimating the global cancer incidence and mortality in 2018: GLOBOCAN sources and methods. International Journal of Cancer, 144(8), 1941–1953. https://doi.org/10.1002/ijc.31937
   PubMed Web of Science ®Google Scholar
• Günsel, A., Bilgiçli, A. T., Tüzün, B., Pişkin, H., Atmaca, G. Y., Erdoğmuş, A., & Yarasir, M. N. (2019). Synthesis of tetra-substituted phthalocyanines bearing 2-(ethyl(m-tolyl)amino)ethanol: Computational and photophysicochemical studies. Journal of Photochemistry and Photobiology A: Chemistry, 373, 77–86. https://doi.org/10.1016/j.jphotochem.2018.12.038
   Web of Science ®Google Scholar
• Islam, M. T., Khalipha, A. B. R., Bagchi, R., Mondal, M., Smrity, S. Z., Uddin, S. J., Shilpi, J. A., & Rouf, R. (2019). Anticancer activity of Thymol: A literature‐based review and docking study with Emphasis on its anticancer mechanisms. IUBMB Life, 71(1), 9–19. https://doi.org/10.1002/iub.1935
   PubMed Web of Science ®Google Scholar
• Ismaili, H., Milella, L., Fkih-Tetouani, S., Ilidrissi, A., Camporese, A., Sosa, S., Altinier, G., Della Loggia, R., & Aquino, R. (2004). In vivo topical anti-inflammatory and in vitro antioxidant activities of two extracts of Thymus satureioides leaves. Journal of Ethnopharmacology, 91(1), 31–36. https://doi.org/10.1016/j.jep.2003.11.013
   PubMed Web of Science ®Google Scholar
• Javan, A. J., & Javan, M. J. (2014). Electronic structure of some thymol derivatives correlated with the radical scavenging activity: Theoretical study. Food Chemistry, 165, 451–459. https://doi.org/10.1016/j.foodchem.2014.05.073
   PubMed Web of Science ®Google Scholar
• Kamalı, A., Çakmak, R., & Boğa, M. (2022). Anticholinesterase and antioxidant activities of novel heterocyclic Schiff base derivatives containing an aryl sulfonate moiety. Journal of the Chinese Chemical Society, 69(4), 731–743. https://doi.org/10.1002/jccs.202100511
   Web of Science ®Google Scholar
• Kumar, D., Rawat, D.S, Beena  , Synthesis and antioxidant activity of thymol and carvacrol based Schiff bases,Bioorganic & Medicinal Chemistry Letters, 3. 23 (2013) 641–645, https://doi.org/10.1016/j.bmcl.2012.12.001
   PubMed Web of Science ®Google Scholar
• Kurt, B. Z., Gazioglu, I., Dag, A., Salmas, R. E., Kayık, G., Durdagi, S., & Sonmez, F. (2017). Synthesis, anticholinesterase activity and molecular modeling study of novel carbamate-substituted thymol/carvacrol derivatives. Bioorganic & Medicinal Chemistry, 25(4), 1352–1363. https://doi.org/10.1016/j.bmc.2016.12.037
   PubMed Web of Science ®Google Scholar
• Leiter, A., Veluswamy, R. R., & Wisnivesky, J. P. (2023). The global burden of lung cancer: Current status and future trends. Nature Reviews. Clinical Oncology, 20(9), 624–639. https://doi.org/10.1038/s41571-023-00798-3
   PubMed Web of Science ®Google Scholar
• McTigue, M., Murray, B. W., Chen, J. H., Deng, Y.-L., Solowiej, J., & Kania, R. S. (2012). Molecular conformations, interactions, and properties associated with drug efficiency and clinical performance among VEGFR TK inhibitors. Proceedings of the National Academy of Sciences of the United States of America, 109(45), 18281–18289. 10.1073/pnas.1207759109
   PubMed Web of Science ®Google Scholar
• Merde, İ. B., Önel, G. T., Akkoç, S., Karaköy, Z., & Türkmenoğlu, B. (2023). Focusing on new piperazinyl‐methyl‐3 (2H) pyridazinone based derivatives: Design, synthesis, anticancer activity and computational studies. ChemistrySelect, 8(25), e202300910. https://doi.org/10.1002/slct.202300910
   Web of Science ®Google Scholar
• Merde, İ. B., Önel, G. T., Türkmenoğlu, B., Gürsoy, Ş., & Dilek, E. (2022). Pyridazinones containing the (4-methoxyphenyl) piperazine moiety as AChE/BChE inhibitors: Design, synthesis, in silico and biological evaluation. Medicinal Chemistry Research, 31(11), 2021–2031. https://doi.org/10.1007/s00044-022-02968-x
   Web of Science ®Google Scholar
• Morgan, E., Arnold, M., Gini, A., Lorenzoni, V., Cabasag, C. J., Laversanne, M., Vignat, J., Ferlay, J., Murphy, N., & Bray, F. (2023). Global burden of colorectal cancer in 2020 and 2040: Incidence and mortality estimates from GLOBOCAN. Gut, 72(2), 338–344. https://doi.org/10.1136/gutjnl-2022-327736
   PubMed Web of Science ®Google Scholar
• Negi, B., & Rawat, D. S. (2018). Antituberculosis activity evaluation of thymol Schiff bases. Chemical Biology, 8, 244–254.
   Google Scholar
• Nesterkina, M., & Kravchenko, I. (2017). Synthesis and pharmacological properties of novel esters based on monoterpenoids and glycine. Pharmaceuticals, 10(4), 47–55. https://doi.org/10.3390/ph10020047
   Google Scholar
• Önem, E., Tüzün, B., & Akkoç, S. (2022). Anti-quorum sensing activity in Pseudomonas aeruginos a PA01 of benzimidazolium salts: Electronic, spectral and structural investigations as theoretical approach. Journal of Biomolecular Structure & Dynamics, 40(15), 6845–6856. https://doi.org/10.1080/07391102.2021.1890222
   PubMed Web of Science ®Google Scholar
• Park, J. H., Liu, Y., Lemmon, M. A., & Radhakrishnan, R. (2012). Erlotinib binds both inactive and active conformations of the EGFR tyrosine kinase domain. The Biochemical Journal, 448(3), 417–423. https://doi.org/10.1042/BJ20121513
   PubMed Web of Science ®Google Scholar
• Rajput, J. D., Bagul, S. D., & Bendre, R. S. (2017). Design, synthesis, biological screenings and docking simulations of novel carvacrol and thymol derivatives containing acetohydrazone linkage. Research on Chemical Intermediates, 43(8), 4893–4906. https://doi.org/10.1007/s11164-017-2919-2
   Web of Science ®Google Scholar
• Rajput, J. D., Bagul, S. D., Hosamani, A. A., Patil, M. M., & Bendre, R. S. (2017). Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage. Research on Chemical Intermediates, 43(10), 5377–5393. https://doi.org/10.1007/s11164-017-2933-4
   Web of Science ®Google Scholar
• Schrödinger, S. (2021a). Release 2021-2: Glide, LLC, New York, NY.
   Google Scholar
• Schrödinger, S. (2021b). Release 2021-2: LigPrep, LLC, New York, NY.
   Google Scholar
• Schrödinger, S. (2021c). Release 2021-2: Prime, LLC, New York, NY.
   Google Scholar
• Schüz, J., & Espina, C. (2021). The eleventh hour to enforce rigorous primary cancer prevention. Oncol, 15, 741–743. https://doi.org/10.1002/18780261.12927
   Google Scholar
• Sharma, P., Jhawat, V., Mathur, P., & Dutt, R. (2022). Innovation in cancer therapeutics and regulatory perspectives. Medical Oncology, 39(5), 76. https://doi.org/10.1007/s12032-022-01677-0
   PubMed Web of Science ®Google Scholar
• Souza, V. V. M. A., Almeida, J. M., Barbosa, L. N., & Silva, N. C. C. (2022). Citral, carvacrol, eugenol and thymol: Antimicrobial activity and its application in food. Journal of Essential Oil Research. 34(3), 181–194. https://doi.org/10.1080/10412905.2022.2032422
   Web of Science ®Google Scholar
• Sung, H., Ferlay, J., Siegel, R. L., Laversanne, M., Soerjomataram, I., Jemal, A., & Bray, F. (2021). GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries. CA: Cancer, J. Clin, 71(3), 209–249. https://doi.org/10.3322/caac.21660
   PubMed Web of Science ®Google Scholar
• Türkmenoğlu, B. (2022). Investigation of novel compounds via in silico approaches of EGFR inhibitors as anticancer agents. Journal of the Indian Chemical Society. 99(8), 100601. https://doi.org/10.1016/j.jics.2022.100601
   Web of Science ®Google Scholar
• Verma, R. S., Padalia, R. C., Chanotiya, C. S., & Chauhan, A. (2010). Chemical investigation of the essential oil of Thymus linearis (Benth. ex Benth) from western Himalaya. Natural Product Research, 24(20), 1890–1896. https://doi.org/10.1080/14786411003754322
   PubMed Web of Science ®Google Scholar
• Wang, J.-J., Lei, K.-F., & Han, F. (2018). Tumor microenvironment: Recent advances in various cancer treatments. European Review for Medical and Pharmacological Sciences, 22(12), 3855–3864. https://doi.org/10.26355/eurrev20180615270
   PubMed Web of Science ®Google Scholar
• Yıldız, U., Şengül, A., Kandemir, I., Cömert, F., Akkoç, S., & Coban, B. (2019). The comparative study of the DNA binding and biological activities of the quaternized dicnq as a dicationic form and its platinum(II) heteroleptic cationic complex. Bioorganic Chemistry, 87, 70–77. https://doi.org/10.1016/j.bioorg.2019.03.009
   PubMed Web of Science ®Google Scholar