Synthesis, Solvatochromic Analysis and Theoretical Studies of 3-((1H-benzo[d][1,2,3]triazole-1-yl)methyl)-4- phenylethyl -1H-1,2,4-triazole-5(4H)-thione

Year 2023, , 568 - 577, 27.06.2023

Zuhal Karagöz , Umut İbrahim Oguz , Murat Genç

https://doi.org/10.17798/bitlisfen.1279575

Abstract

The novel 2-(2-(1H-benzo[d][1,2,3]triazole-1-yl)acetyl)-N- phenylethyl hydrazinecarbothioamide (1) was synthesized by reaction of 2-(1H-benzo[d][1,2,3]triazole-1-yl)acetohydrazide and 2-phenylethylisothiocyanate. The condensation of compound 1 in presence of sodium hydroxide gave 3-((1H-benzo[d][1,2,3]triazole-1-yl)methyl)-4- phenylethyl -1H-1,2,4-triazole-5(4H)-thione (BPT). Theoretical calculations of BPT have been studied. The 6-311G+ (d,p) basis set was used for the DFT computations. The calculated spectra matched up with what was observed; hence the findings were confirmed. The same theoretical calculation procedure was used to examine BPT's LUMO, HOMO, and other associated energy values. To find out whether solute-solvent interactions were peculiar to BPT, the Catalán–Kamlet–Taft solvent parameter was used. BPT also plays an important role in antibacterial action, as shown by docking studies

Keywords

Benzotriazole, DFT, Microwave irradiation, Docking

Supporting Institution

The Adiyaman University Research Foundation (FEFYL/2012-0006) generously funded this research project, and we are grateful for their assistance.

Project Number

FEFYL/2012-0006

References

• [1] S. Rachakonda and L. Cartee, “Challenges in antimicrobial drug discovery and the potential of nucleoside antibiotics,” Curr. Med. Chem., vol. 11, no. 6, pp. 775–793, 2004
• [2] C. Nathan, “Antibiotics at the crossroads,” Nature, vol. 431, no. 7011, pp. 899–902, 2004
• [3] K. Cheng, Q.-Z. Zheng, Y. Qian, L. Shi, J. Zhao, and H.-L. Zhu, “Synthesis, antibacterial activities and molecular docking studies of peptide and Schiff bases as targeted antibiotics,” Bioorg. Med. Chem., vol. 17, no. 23, pp. 7861–7871, 2009.
• [4] T. M. Barbosa and S. B. Levy, “The impact of antibiotic use on resistance development and persistence,” Drug Resist. Updat., vol. 3, no. 5, pp. 303–311, 2000.
• [5] K. S. Kiran, M. K. Kokila, Guruprasad, and Niranjan, “Crystal structure determination and molecular docking studies of 4- (5-Phenyl pyrazin-2-yl)-4h-1,2,4 Triazole-3-thiol with focal adhesion kinase inhibitors,” Open Chem. J., vol. 3, no. 1, pp. 69–74, 2016
• [6] Y. Sert, A. A. El-Emam, E. S. Al-Abdullah, A.-M. S. Al-Tamimi, C. Cırak, and F. Ucun, “Use of vibrational spectroscopy to study 4-benzyl-3-(thiophen-2-yl)-4,5-dihydro-1H-1,2,4-triazole-5-thione: A combined theoretical and experimental approach,” Spectrochim. Acta A Mol. Biomol. Spectrosc., vol. 126, pp. 280–290, 2014.
• [7] Y.-P. Hou et al., “Synthesis and antitumor activity of 1,2,4-triazoles having 1,4-benzodioxan fragment as a novel class of potent methionine aminopeptidase type II inhibitors,” Bioorg. Med. Chem., vol. 19, no. 20, pp. 5948–5954, 2011
• [8] A. Šermukšnytė, K. Kantminienė, I. Jonuškienė, I. Tumosienė, and V. Petrikaitė, “The effect of 1,2,4-triazole-3-thiol derivatives bearing hydrazone moiety on cancer cell migration and growth of melanoma, breast, and pancreatic cancer spheroids,” Pharmaceuticals (Basel), vol. 15, no. 8, p. 1026, 2022.
• [9] H. Alsaad, A. Kubba, L. H. Tahtamouni, and A. H. Hamzah, “Synthesis, docking study, and structure activity relationship of novel anti-tumor 1, 2, 4 triazole derivatives incorporating 2-(2, 3- dimethyl aminobenzoic acid) moiety,” Farmatsiia (Sofia), vol. 69, no. 2, pp. 415–428, 2022.
• [10] D. C. Kahraman, E. Bilget Guven, P. S. Aytac, G. Aykut, B. Tozkoparan, and R. Cetin Atalay, “A new triazolothiadiazine derivative inhibits stemness and induces cell death in HCC by oxidative stress dependent JNK pathway activation,” Sci. Rep., vol. 12, no. 1, p. 15139, 2022.
• [11] L. B. de O. Freitas et al., “Synthesis and antiproliferative activity of 8-hydroxyquinoline derivatives containing a 1,2,3-triazole moiety,” Eur. J. Med. Chem., vol. 84, pp. 595–604, 2014
• [12] V. Spanò et al., “Synthesis of a new class of pyrrolo[3,4-h]quinazolines with antimitotic activity,” Eur. J. Med. Chem., vol. 74, pp. 340–357, 2014.
• [13] R. Marulasiddaiah, R. G. Kalkhambkar, and M. V. Kulkarni, “Synthesis and biological evaluation of cyclic imides with coumarins and azacoumarins,” Open J. Med. Chem., vol. 02, no. 03, pp. 89–97, 2012.
• [14] P. Diana et al., “Synthesis and antitumor activity of 3-(2-phenyl-1,3-thiazol-4-yl)-1H-indoles and 3-(2-phenyl-1,3-thiazol-4-yl)-1H-7-azaindoles,” ChemMedChem, vol. 6, no. 7, pp. 1300–1309, 2011.
• [15] Y.-P. Hou et al., “Synthesis and antitumor activity of 1,2,4-triazoles having 1,4-benzodioxan fragment as a novel class of potent methionine aminopeptidase type II inhibitors,” Bioorg. Med. Chem., vol. 19, no. 20, pp. 5948–5954, 2011.
• [16] A. C. Pasqualotto, K. O. Thiele, and L. Z. Goldani, “Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole,” Curr. Opin. Investig. Drugs, vol. 11, no. 2, pp. 165–174, 2010
• [17] J. Xu et al., “Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives,” Eur. J. Med. Chem., vol. 46, no. 7, pp. 3142–3148, 2011
• [18] C. Tratrat et al., “Design, synthesis and biological evaluation of new substituted 5-benzylideno- 2-adamantylthiazol[3,2-b][1,2,4]triazol-6(5H)ones. Pharmacophore models for antifungal activity” Arabian Journal of Chemistry, vol.11, no. 4, pp. 573-590, 2018
• [19] G. V. Suresh Kumar, Y. Rajendraprasad, B. P. Mallikarjuna, S. M. Chandrashekar, and C. Kistayya, “Synthesis of some novel 2-substituted-5-[isopropylthiazole] clubbed 1,2,4-triazole and 1,3,4-oxadiazoles as potential antimicrobial and antitubercular agents,” Eur. J. Med. Chem., vol. 45, no. 5, pp. 2063–2074, 2010.
• [20] M. Strzelecka and P. Świątek, “1,2,4-triazoles as important antibacterial agents,” Pharmaceuticals (Basel), vol. 14, no. 3, p. 224, 2021.
• [21] A. A. El-Emam, A.-M. S. Al-Tamimi, M. A. Al-Omar, K. A. Alrashood, and E. E. Habib, “Synthesis and antimicrobial activity of novel 5-(1-adamantyl)-2-aminomethyl-4-substituted-1,2,4-triazoline-3-thiones,” Eur. J. Med. Chem., vol. 68, pp. 96–102, 2013.
• [22] A. Pachuta-Stec, “Antioxidant Activity of 1,2,4-Triazole and its Derivatives: A Mini-Review,” Mini Rev. Med. Chem., vol. 22, no. 7, pp. 1081–1094, 2022.
• [23] J. K. Sugden and T. O. Yoloye, “Medicinal applications of indole derivatives,” Pharm. Acta Helv., vol. 53, no. 3–4, pp. 65–92, 1978
• [24] “SciFinder® Login,” Cas.org. [Online]. Available: https://scifinder.cas.org/scifinder/view/scifinder/scifinderExplore.jsf. [Accessed: 16-Jun-2023].
• [25] A. D. Becke, “Density‐functional thermochemistry. III. The role of exact exchange,” J. Chem. Phys., vol. 98, no. 7, pp. 5648–5652, 1993
• [26] C. Lee, W. Yang, and R. G. Parr, “Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density,” Phys. Rev. B Condens. Matter, vol. 37, no. 2, pp. 785–789, 1988.
• [27] K. Wolinski, J. F. Hinton, and P. Pulay, “Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations,” J. Am. Chem. Soc., vol. 112, no. 23, pp. 8251–8260, 1990.
• [28] K. Bahgat and S. Fraihat, “Normal coordinate analysis, molecular structure, vibrational, electronic spectra and NMR investigation of 4-Amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione by ab initio HF and DFT method,” Spectrochim. Acta A Mol. Biomol. Spectrosc., vol. 135, pp. 1145–1155, 2015
• [29] S. Muthu, T. Rajamani, M. Karabacak, and A. M. Asiri, “Vibrational and UV spectra, first order hyperpolarizability, NBO and HOMO-LUMO analysis of 4-chloro-N-(2-methyl-2,3-dihydroindol-1-yl)-3-sulfamoyl-benzamide,” Spectrochim. Acta A Mol. Biomol. Spectrosc., vol. 122, pp. 1–14, 2014
• [30] K. Bahgat and S. Fraihat, “Normal coordinate analysis, molecular structure, vibrational, electronic spectra and NMR investigation of 4-Amino-3-phenyl-1H-1,2,4-triazole-5(4H)-thione by ab initio HF and DFT method,” Spectrochim. Acta A Mol. Biomol. Spectrosc., vol. 135, pp. 1145–1155, 2015.
• [31] M. D. Diener and J. M. Alford, “Isolation and properties of small-bandgap fullerenes,” Nature, vol. 393, no. 6686, pp. 668–671, 1998.
• [32] J.B. Foresman, E. FrischGaussian, Pittsburgh, PA, 1993. NIST Chemistry Webbook, IR database, http://srdata.nist.gov/cccbdb.
• [33] H.M. Jamroz,Vibrational energy distribution analysis: VEDA 4 program, Warsaw, 2004
• [34] A. Lakshmi and V. Balachandran, “Rotational isomers, NBO and spectral analyses of N-(2-hydroxyethyl) phthalimide based on quantum chemical calculations,” J. Mol. Struct., vol. 1033, pp. 40–50, 2013.
• [35] M. Genç, “Solvatochromic analysis and DFT computational study of N-(hexyl)-N-(5-(3-hydroxynaphthyl-2-yl)-1,3,4-oxadiazol-2-yl)amine,” Appl. Phys. A Mater. Sci. Process., vol. 125, no. 6, 2019.
• [36] J. Catalán and H. Hopf, “Empirical treatment of the inductive and dispersive components of Solute−Solvent interactions: The solvent polarizability (SP) scale: Inductive and dispersive components of Solute−Solvent interactions,” European J. Org. Chem., vol. 2004, no. 22, pp. 4694–4702, 2004
• [37] M. J. Kamlet, J. L. M. Abboud, M. H. Abraham, and R. W. Taft, “Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, .pi.*, .alpha., and .beta., and some methods for simplifying the generalized solvatochromic equation,” J. Org. Chem., vol. 48, no. 17, pp. 2877–2887, 1983.
• [38] S. M. Hiremath et al., “Synthesis of 5-(5-methyl-benzofuran-3-ylmethyl)-3H- [1, 3, 4] oxadiazole-2-thione and investigation of its spectroscopic, reactivity, optoelectronic and drug likeness properties by combined computational and experimental approach,” Spectrochim. Acta A Mol. Biomol. Spectrosc., vol. 205, pp. 95–110, 2018.