Bazı Sentezlenmiş 3-Arilamino-5-[2-(Sübstitüe Edilmiş 1-İmidazol) Etil 1]-1,2,4-Triazol Türevlerinin Teorik İncelenmesi

Yıl 2023, , 76 - 91, 30.04.2023

Aybek Yiğit , Zeynep Şilan Turhan

https://doi.org/10.53433/yyufbed.1123076

Cited By: 1

Öz

Bu çalışmada, sekiz adet 1,2,4-triazol türevinin kimyasal, doğrusal olmayan optik özellikleri ve antibakteriyel aktivite parametrelerini elde etmek için kuantum kimyasal hesaplamaları yapılmış ve yorumlanmıştır. Ayrıca, sekiz bileşiğin en kararlı yapıları, yoğunluk fonksiyonel teorisinde B3LYP/6-311++G(d,p) kullanılarak optimize edilerek bulunmuştur. Optimize edilmiş moleküllere ait sonuçlardan yola çıkarak HOMO-LUMO enerjileri ve bu enerji değerlerinden hesaplanan kimyasal parametreler (I.iyonizasyon potansiyeli, A: elektron ilgisi, ΔE enerji aralığı, χ: elektronegatiflik, σ: moleküler yumuşaklık, η: moleküler sertlik, ω: elektrofilik indeks, ε: nükleofilik indeks, μ: kimyasal potansiyel) değerleri belirlendi.

Anahtar Kelimeler

Antimikrobiyal, DFT, Doğrusal olmayan optik özellikler, İmidazol, Kimyasal parametreler, 1,2,4-triazole

Theoretical Investigation of Some Synthesized 3-Arylamino-5-[2-(Substituted 1-imidazole) Ethyl 1]-1,2,4-Triazole Derivatives

Öz

In this study, quantum chemical calculations were made and interpreted to obtain chemical, nonlinear optical properties and antibacterial activity parameters of eight 1,2,4-triazole derivatives. In addition, the most stable structure was found in the B3LYP/6-311++G(d,p) method by optimizing the density functional theory of eight compounds. Based on the results of optimized molecules, HOMO-LUMO energies and chemical parameters calculated from these energy values (I.ionization potential, A: electron affinity, ΔE energy gap, χ: electronegativity, σ: molecular softness, η: molecular hardness, ω: electrophilic index, ε: nucleophilic index, μ: chemical potential) values were determined.

Anahtar Kelimeler

Antimicrobial, Chemical Parameters, DFT, Imidazole, Nonlinear Optical Properties, 1,24-triazole

Kaynakça

• Acosta, A. C., Cardoso, M. V., Oliveira Filho, G. B., Pinheiro Junior, J. W., Leite, A. C. L., & Mota, R. A. (2021). Antimicrobial properties of heterocyclic compounds against clinical mastitis isolates. Pesquisa Veterinária Brasileira, 41. doi:10.1590/1678-5150-PVB-6862
• Ahmad, A., Varshney, H., Rauf, A., Sherwani, A., & Owais, M., (2017). Synthesis and anticancer activity of long chain substituted 1,3,4-oxadiazol-2-thione,1,2,4-triazol-3-thione and 1,2,4-triazolo [3,4-b]-1,3,4-thiadiazine derivatives. Arabian Journal of Chemistry, 10, S3347-S3357. doi:10.1016/j.arabjc.2014.01.015
• Amir, M., Kumar, H., & Javed, S. A. (2008). Condensed bridgehead nitrogen heterocyclic system: Synthesis and pharmacological activities of 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole derivatives of ibuprofen and biphenyl-4-yloxy acetic acid. European Journal of Medicinal Chemistry, 43(10), 2056-2066. doi:10.1016/j.ejmech.2007.09.025
• Arivazhagan M., & Subhasini V. P. (2012). Quantum chemical studies on structure of 2-amino-5-nitropyrimidine. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 91, 402-410. doi:10.1016/j.saa.2012.02.018
• Bagihalli, G. B., Avaji, P. G., Patil, S. A., & Badami, P. S. (2008). Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co (II), Ni (II) and Cu (II) complexes with 1,2,4-triazole Schiff bases. European Journal of Medicinal Chemistry, 43(12), 2639-2649. doi:10.1016/j.ejmech.2008.02.013
• Beytur, M., Irak, Z. T., Manap, S., & Yüksek, H. (2019). Synthesis, characterization and theoretical determination of corrosion inhibitor activities of some new 4, 5-dihydro-1H-1, 2, 4-triazol-5-one derivatives. Heliyon, 5(6), e01809. doi:10.1016/j.heliyon.2019.e01809
• Beytur, M., & Avinca, I. (2021). Molecular, electronic, nonlinear optical and spectroscopic analysis of heterocyclic 3-substituted-4-(3-methyl-2-thienylmethyleneamino)-4, 5-dihydro-1H-1, 2, 4-triazol-5-ones: experiment and DFT calculations. Heterocyclic Communications, 27(1), 1-16. doi:10.1515/hc-2020-0118
• Chou, T. C., & Talalay, P. (1984). Quantitative analysis of dose-effect relationships: the combined effects of multiple drugs or enzyme inhibitors. Advances in Enzyme Regulation, 22, 27-55. doi:10.1016/0065-2571(84)90007-4
• Demirayak, Ş., Benkli, K., & Güven, K. (2000). Synthesis and antimicrobial activities of some 3-arylamino-5-[2-(substituted 1-imidazolyl) ethyl]-1, 2, 4-triazole derivatives. European Journal of Medicinal Chemistry, 35(11), 1037-1040. doi:10.1016/S0223-5234(00)01178-8
• Dennington, R., Keith, T., & Millam, J. (2009). GaussView, Version 5. Semichem Inc., Shawnee Mission KS, USA.
• Erkan Kariper, S., Sayın, K. & Karakaş, D. (2014). Salisilaldehid ve anilin ligandlarını içeren sekiz oksovanadyum IV kompleksi üzerine teorik çalışmalar. Hacettepe Journal of Biology and Chemistry, 42(3), 337-342.
• Eswaran, S., Adhikari, A. V., & Shetty, N. S. (2009). Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. European Journal of Medicinal Chemistry, 44(11), 4637-4647. doi:10.1016/j.ejmech.2009.06.031
• Fletcher, R. A., Hofstra, G., & Gao, J. G. (1986). Comparative fungitoxic and plant growth regulating properties of triazole derivatives. Plant and Cell Physiology, 27(2), 367-371. doi:10.1093/oxfordjournals.pcp.a077111
• Foresman, J. B., & Frisch, A. (1996). Exploring Chemistry with Electronic Structure Methods. Pittsburgh, PA, USA: Gaussian, Inc.
• Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., ... & Fox, D. J. (2009). GAUSSIAN09. Gaussian Inc., Wallingford, CT, USA.
• Fukui, K. (1982). The role of frontier orbitals in chemical reactions (Nobel Lecture). Angewandte Chemie International Edition in English, 21(11), 801-809. doi:10.1002/anie.198208013
• Govindarajan, M., Periandy, S., & Carthigayen, K. (2012). FT-IR and FT-Raman Spectra, Thermo Dynamical Behavior, HOMO and LUMO, UV, NLO Properties, Computed Frequency Estimation Analysis and Electronic Structure Calculations on α-Bromotoluene. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 97, 411-422. doi:10.1016/j.saa.2012.06.028
• Gökçe, H., & Bahçeli, S. (2011). A study on quantum chemical calculations of 3-, 4-nitrobenzaldehyde oximes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 79, 1783-1793. doi:10.1016/j.saa.2011.05.057
• Gundlewad, G. B., & Patil, B. R. (2018). Synthesis and Evaluation of Some Novel 2‐Amino‐4‐Aryl Thiazoles for Antitubercular Activity. Journal of Heterocyclic Chemistry, 55(3), 769-774. doi:10.1002/jhet.3098
• Gümüş, PH, Tamer, Ö., Avcı, D., & Atalay Y., (2015). 4-(Metoksimetil)-1,6- dimetil-2-okso-1,2-dihidropiridin-3-karbonitril molekülünün teorik olarak incelenmesi. Sakarya Üniversitesi Fen Bilimleri Dergisi, 19(3), 303-311. doi:10.16984/saufenbilder.86449
• Gümüş, S., & Gümüş, A. (2017). A computational study on a series of phenanthrene and phenanthroline based potential organic photovoltaics. Macedonian Journal of Chemistry and Chemical Engineering, 36(2), 239-249. doi:10.20450/mjcce.2017.1199
• Holla, B. S., Veerendra, B., Shivananda, M. K., Poojary, B. (2003). Synthesis characterization and anticancer activity studies on some Mannich bases derived from 1,2,4-triazoles. European Journal of Medicinal Chemistry, 38(7-8), 759-767. doi:10.1016/S0223-5234(03)00128-4
• Invidiata, F. P., Simoni, D., Scintu, F., & Pinna, N. (1996). 3, 6-Disubstituted 1, 2, 4-triazolo [3, 4-b][1, 3, 4] thiadiazoles: synthesis, antimicrobial and antiviral activity. II. Farmaco (Societa Chimica Italiana: 1989), 51(10), 659-664. https://europepmc.org/article/med/8981756
• Irak, Z. T., & Beytur, M. (2019). 4-Benzilidenamino-4, 5-dihidro-1H-1, 2, 4-triazol-5-on türevlerinin antioksidan aktivitelerinin teorik olarak incelenmesi. Journal of the Institute of Science and Technology, 9 (1), 512-521. doi:10.21597/jist.481990
• Jesudason, E., Sridhar, S. K., Malar, E. J., Shanmugapandiyan, P., Inayathullah, M., Arul, V., Selvaraj D., & Jayakumar, R. (2009). Synthesis, pharmacological screening, quantum chemical and in vitro permeability studies of N-Mannich bases of benzimidazoles through bovine cornea. European Journal of Medicinal Chemistry, 44, 2307-2312. doi:10.1016/j.ejmech.2008.03.043
• Kaya, S., Kariper, S. E., Ungördü, A., & Kaya, C. (2014). Effect of some electron donor and electron acceptor groups on stability of complexes according to the principle of HSAB. Journal of New Results in Science, 3(4), 82-89.
• Khan, S. A., Asiri, A. M., & Sharma, K. (2017). Efficient microwave assisted synthesis and computational study of isoxazole Schiff base as an antibacterial agent. Indian Jornal of Chemistry, 56 B, 453-457.
• Kiyooka, S. I., Kaneno, D., & Fujiyama, R. (2013). Parr’s index to describe both electrophilicity and nucleophilicity. Tetrahedron Letters, 54(4), 339-342. doi:10.1016/j.tetlet.2012.11.039
• Koopmans, T. (1933). Ordering of wave functions and eigenenergies to the individual electrons of an atom. Physica, 1, 104-113. doi:10.1016/S0031-8914(34)90011-2
• Kuş, C., Ayhan-Kılcıgil, G., Özbey, S., Kaynak, F. B., Kaya, M., Çoban, T., & Can-Eke, B. (2008). Synthesis and antioxidant properties of novel N-methyl-1,3,4-thiadiazol-2-amine and 4-methyl-2H-1,2,4-triazole-3(4H)-thione derivatives of benzimidazole class. Bioorganic & Medicinal Chemistry, 16(8), 4294-4303. doi:10.1016/j.bmc.2008.02.077
• Lewis, D. F. V., Ioannides, C., & Parke, D. V. (1994). Interaction of a series of nitriles with the alcohol-inducible isoform of P450:Computer analysis of structure activity relationships. Xenobiotica, 24(5), 401-408. doi:10.3109/00498259409043243
• Malbec, F., Milcent, R.., Vicart, P., & Bure, A. M. (1984). Synthesis of new derivatives of 4‐amino‐2,4‐dihydro‐1,2,4‐triazol‐3‐one as potential antibacterial agents. Journal of Heterocyclic Chemistry, 21 (6), 1769-1774. doi:10.1002/jhet.5570210641
• Manap, S., & Medetalibeyoğlu, H. (2018, Aralık). Investigation of theoretical/experimental spectroscopic and electronic properties of 1- Acetyl-3-Methyl-4-[3-(2-Methylbenzoxy)-4-Methoxy]-Benzylidenamino4,5-Dihydro-1H-1,2,4-Triazol-5-One by using 6-31G(d,p) method. IV. Uluslararası Mesleki ve Teknik Bilimler Kongresi, Erzurum.
• Masoud, M. S., Ali, A. E., Shaker, M. A., & Elasala, G. S. (2012). Synthesis, computational, spectroscopic, thermal and antimicrobial activity studies on some metal–urate complexes. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 90, 93-108. doi:10.1016/j.saa.2012.01.028
• Méhes, G., Nomura, H., Zhang, Q., Nakagawa, T., & Adachi, C. (2012). Enhanced electroluminescence efficiency in a spiro‐acridine derivative through thermally activated delayed fluorescence. Angewandte Chemie International Edition, 51(45), 11311-11315. doi:10.1002/anie.201206289
• Mishra, L., Ram, V. J., & Kushwaha, D. S. (1989). Preparation and structure of cobalt (II), nickel (II), copper (II) and zinc (II) complexes with 3-amino-5-(α/β) pyridyl-1,2,4-triazoles. Transition Metal Chemistry, 14 (5), 384-386. doi:10.1007/BF01032516
• Mohamed, G. G., & Gad-Elkareem, M. A. (2007). Synthesis, characterization and thermal studies on metal complexes of new azo compounds derived from sulfa drugs. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 68(5), 1382-1387. doi:10.1016/j.saa.2007.01.034
• Nakagawa, T., Ku, S. Y., Wong, K. T., & Adachi, C. (2012). Electroluminescence based on thermally activated delayed fluorescence generated by a spirobifluorene donor–acceptor structure. Chemical Communications, 48(77), 9580-9582. doi:10.1039/C2CC31468A
• Nasu, K., Nakagawa, T., Nomura, H., Lin, C. J., Cheng, C. H., Tseng, M. R., Yasuda, T., & Adachi, C. (2013). A highly luminescent spiro-anthracenone-based organic light-emitting diode exhibiting thermally activated delayed fluorescence. Chemical Communications, 49(88), 10385-10387. doi:10.1039/C3CC44179B
• Papadopoulos, M. G., Sadlej, A. J., & Leszczynski, J. (2006). Non-linear Optical Properties of Matter. Dordrecht, Netherlands: Springer.
• Parr, R. G., & Yang, W. (1989). Density Functional Theory in Atoms and Molecules. New York, USA: Oxford Science Publications.
• Rejhova, A., Opattova, A., Čumová, A., Slíva, D., & Vodička, P., (2018). Natural compounds and combination therapy in colorectal cancer treatment. European Journal of Medicinal Chemistry, 144, 582-594. doi:10.1016/j.ejmech.2017.12.039
• Salgın-Gökşen, U., Gökhan-Kelekçi, N., Göktaş, Ö., Köysal, Y., Kılıç, E., Işık, Ş., & Özalp, M. (2007). 1-Acylthiosemicarbazides, 1,2,4-triazole-5 (4H)-thiones,1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. Bioorganic and Medicinal Chemistry, 15(17), 5738-5751. doi:10.1016/j.bmc.2007.06.006
• Sastri, V. S., & Perumareddi, J. R. (1997). Molecular orbital theoretical studies of some organic corrosion inhibitors. Corrosion, 53(8), 617-622. https://doi.org/10.5006/1.3290294
• Sayın, K., & Karakas, D. (2013). Quantum chemical studies on the some inorganic corrosion inhibitors. Corrosion Science, 77, 37-45. doi:10.1016/j.corsci.2013.07.023
• Sayin, K., & Karakaş, D. (2017). Theoretical study on the antitumor properties of Ru (II) complexes containing 2-pyridyl, 2-pyridine-4-carboxylic acid ligands. Journal of Molecular Structure, 1149, 473-486. doi:10.1016/j.molstruc.2017.07.079
• Sebastian, S., Sylvestre, S., Sundaraganesan, N., Amalanathan, M., Ayyapan, S., Oudayakumar, K., & Karthikeyan, B. (2013). Vibrational spectra, molecular structure, natural bond orbital, first order hyperpolarizability, TD-DFT and thermodynamic analysis of 4-amino-3-hydroxy-1-naphthalenesulfonic acid by DFT approach. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 107, 167-178. doi:10.1016/j.saa.2013.01.041
• Shaker, R. M., Mahmoud, A. F., & Abdel-Latif, F. F. (2005). Synthesis and biological activities of novel 1,4-bridged bis-1,2,4-triazoles,bis-1,3,4-thiadiazoles and bis-1,3,4-oxadiazoles. Phosphorus, Sulfur and Silicon, 180(2), 397-406. doi:10.1080/104265090509199
• Singh, K., Barwa, M. S., & Tyagi, P. (2007). Synthesis and characterization of cobalt (II), nickel (II), copper (II) and zinc (II) complexes with Schiff base derived from 4-amino-3-mercapto-6-methyl-5-oxo-1,2,4-triazine. European Journal of Medicinal Chemistry, 42(3), 394-402. doi:10.1016/j.ejmech.2006.10.016
• Turhan Irak, Z. Ş., & Gümüş, S. (2017). Heterotricyclic compounds via click reaction: a computational study. Noble International Journal of Scientific Research, 1(7), 80-89.
• Turhan Irak, Z., Gümüs, A., & Gümüs, S. (2019). Investıgatıon of TADF propertıes of novel donor-acceptor type pyrazıne derivatives. Journal of the Chilean Chemical Society, 64(1), 4303-4309. doi:10.4067/s0717-97072019000104303
• Yüksek, H., Özdemir, G., Manap, S., Yılmaz, Y., Kotan, G., Gürsoy-Kol, Ö., & Alkan, M. (2020). Synthesis and Investigations of Antimicrobial, Antioxidant Activities of Novel Di-[2-(3-alkyl/aryl-4, 5-dihydro-1H-1, 2, 4-triazol-5-one-4-yl)-azomethinephenyl] Isophtalates and Mannich Base Derivatives. ACTA Pharmaceutica Sciencia, 58(1), 49-68. doi:10.23893/1307-2080.APS.05804
• Zhou, X., Cui, J., Li, Z. H., Wang, G., Liu, Z., & Zhou, M. (2013). Carbonyl bonding on oxophilic metal centers: Infrared photodissociation spectroscopy of mononuclear and dinuclear titanium carbonyl cation complexes. The Journal of Physical Chemistry A, 117(7), 1514-1521. doi:10.1021/jp3120429