* Corresponding Author
Synthesis, Characterization and Antioxidant Evaluation of Some Tetrazole Derivatives
https://doi.org/10.22146/ijc.74912 Meinaa Jaber Dalal(1), Athraa Hameed Mekky(2*)
(1) Department of Chemistry, College of Science, University of Thi-Qar, Thi-Qar, 64001, Iraq
(2) Department of Chemistry, College of Science, University of Thi-Qar, Thi-Qar, 64001, Iraq
(*) Corresponding Author
Abstract
The present study introduces the synthesis of two series of tetrazole derivatives. Firstly, monosubstituted S1 was prepared by the reaction of ethyl 4-aminobenzoate with an amount of sodium azide and triethyl orthoformate in hot glacial acetic acid. Then, ethyl 4-(1H-tetrazol-1-yl) benzoate S1 was treated with a solution of hydrazine hydrate to prepare acetohydrazide S2. After that, tetrazole derivatives S3-S4 were prepared via the reaction of acetohydrazide S2 with various aromatic aldehydes. Secondly, compound 1,5-disubstituted tetrazole S5 was prepared from the reaction of aryl isothiocyanate with sodium azide in water presence. Then alkylation to compound S5 was made with ethyl chloroacetate to produce S6. In the next step, S6 was reacted with hydrazine hydrate to get acetohydrazide S7. Moreover, the produced S7 was reacted with some aromatic aldehydes for the synthesis of S8-S10. The structures of synthesized compounds were confirmed by the different available spectral methods, i.e., FTIR, 1H-NMR and 13C-NMR spectroscopy. The antioxidant activity of the synthesized compounds was evaluated by the use of 2,2-diphenyl-1-picrylhydrazyl. The results showed that compound S10 has the highest value as radical scavenging among the synthesized compounds.
Keywords
References
[1] Nessim, M.I., Elewa, S.I., and Mohamed, M.G., 2018, Synthesis and study antimicrobial activities of some novel tetrazole derivatives, Egypt. J. Chem., 61 (1), 197–206.
[2] Bhaskar, V.H., and Mohite, P.B., 2010, Synthesis, characterization and evaluation of anticancer activity of some tetrazole derivatives, J. Optoelectron. Biomed. Mater., 2 (4), 249–259.
[3] Maruthamuthu, M., Rajam, S., Stella, C.R., Dileepan, A.G.B., and Ranjith, R., 2016, The chemistry and biological significance of imidazole, benzimidazole, benzoxazole, tetrazole and quinazolinone nucleus, J. Chem. Pharm. Res., 8 (5), 505–526.
[4] Bhaskar, V.H., and Mohite, P.B., 2011, Synthesis analgesic, anti-inflammatory and antimicrobial activities of some 1-[5-(substitutedphenyl)-4,5-dihydro-1H-pyrazol-3-yl]-5-phenyl-1H-tetrazole, J. Optoelectron. Biomed. Mater., 3 (1), 7–16.
[5] Malik, M.A., Al-Thabaiti, S.A., and Malik, M.A., 2012, Synthesis, structure optimization and antifungal screening of novel tetrazole ring bearing acyl-hydrazones, Int. J. Mol. Sci., 3 (9), 10880–10898.
[6] Qian, A., Zheng, Y., Wang, R., Wei, J., Cui, Y., Cao, X., and Yang, Y., 2017, Design, synthesis, and structure-activity relationship studies of novel tetrazole antifungal agents with potent activity, broad antifungal spectrum and high selectivity, Bioorg. Med. Chem. Lett., 28 (3), 344–350.
[7] Vembu, S., Parasuraman, P., and Gopalakrishnan, M., 2014, Design, in silico molecular docking studies, synthesis, spectral characterization and in vitro antifungal evaluation of 1-(4-(1H-tetrazole-1-yl) phenyl)-3-arylprop-2-en-1-ones, Pharma Chem., 6 (5), 35–44.
[8] Kaushik, N., Kumar, N., Kumar, A., and Singh, U.K., 2018, Tetrazoles: Synthesis and biological activity, Immunol., Endocr. Metab. Agents Med. Chem., 18 (1), 3–21.
[9] Özkan, H., and Demirci, H., 2019, Synthesis and antimicrobial and antioxidant activities of sulfonamide derivatives containing tetrazole and oxadiazole rings, J. Heterocycl. Chem., 56 (9), 2528–2535.
[10] Zhang, H.Z., Gan, L.L., Wang, H., and Zhou, C.H., 2017, New progress in azole compounds as antimicrobial agents, Mini-Rev. Med. Chem., 17 (2), 122–166.
[11] George, S., Varma, P.S., Suresh, I., and Shanmugapandiyan, P., 2012, Synthesis, antimicrobial and anti-inflammatory activities of 3-(1-substituted phenyl-1H-tetrazol-5-yl) pyridine derivatives, Asian J. Pharm. Clin. Res., 5 (4), 81–84.
[12] Mikolaichuk, O.V., Zarubaev, V.V., Muryleva, A.А., Esaulkova, Y.L., Spasibenko, D.V., Batyrenko, A.А., Kornyakov, I.V., and Trifonov, R.Е., 2021, Synthesis, structure, and antiviral properties of novel 2-adamantyl-5-aryl-2H-tetrazoles, Chem. Heterocycl. Compd., 57 (4), 442–447.
[13] Asif, M., 2014, Biological potentials of substituted tetrazole compounds, Pharm. Methods, 5 (2), 2–8.
[14] Zhang, J., Wang, S., Ba, Y., and Xu, Z., 2019, Tetrazole hybrids with potential anticancer activity, Eur. J. Med. Chem., 178, 341–351.
[15] Popova, E.A., Protas, A.V., and Trifonov, R.E., 2018, Tetrazole derivatives as promising anticancer agents, Anti-Cancer Agents Med. Chem., 17 (14), 1856–1868.
[16] Samanta, P.K., Biswas, R., Das, T., Nandi, M., Nandi, M., Adhikary, B., Richards, R.M., and Biswas, P., 2019, Mesoporous silica supported samarium as recyclable heterogeneous catalyst for synthesis of 5-substituted tetrazole and 2-substituted benzothiazole, J. Porous Mater., 26 (1), 145–155.
[17] Kaplancıklı, Z.A., Yurttaş, L., Özdemir, A., Turan-Zitouni, G., Çiftçi, G.A., Yıldırım, Ş.U., and Abu Mohsen, U., 2014, Synthesis and antiproliferative activity of new 1,5-disubstituted tetrazoles bearing hydrazone moiety, Med. Chem. Res., 23 (2), 1067–1075.
[18] Maleki, A., and Sarvary, A., 2015, Synthesis of tetrazoles via isocyanide-based reactions, RSC Adv., 5 (75), 60938–60955.
[19] Mohana, K.N., and Kumar, C.B.P., 2013, Synthesis and antioxidant activity of 2-amino-5-methylthiazol derivatives containing 1,3,4-oxadiazole-2-thiol moiety, Int. Scholarly Res. Not., 2013, 620718.
[20] Kosanić, M., Ranković, B.R., and Dasic, M., 2013, Antioxidant and antimicrobial properties of mushrooms, Bulg. J. Agric. Sci., 19 (5), 1040–1046.
[21] Gouda, M.A., Al-Ghorbani, M., Helal, M.H., Salem, M.A., and Hanashalshahaby, E.H.A., 2020, Recent progress on the synthetic routes to 1(5)-substituted 1H-tetrazoles and its analogs, Synth. Commun., 50 (20), 3017–3043.
[22] Mekky, A.H., Sayer, A.H., and Abed, H.J., 2019, Synthesis, antioxidant activity of some novel Schiff base derived from ethyl 4-aminobenzoate, Biochem. Cell. Arch., 19 (1), 1247–1256.
[23] Al-Ajely, M.S., and Yaseen, A.N., 2015, Synthesis and characterization of some new hydrazides and their derivatives, Ibn Al-Haitham J. Pure Appl. Sci., 28 (3), 103–112.
[24] Alsahib, S.A., and Dhedan, R.M., 2021, Synthesis and characterization of some tetrazole derivatives and evaluation of their biological activity, Egypt. J. Chem., 64 (6), 2925–2936.
[25] Al-Bayati, R.I.H., Habib, M.J., and Mekky, A.H., 2015, Synthesis and characterization of new saccharin derivatives, J. Multidiscip. Curr. Res., 3, 61–72.
[26] Abdul-Nabi, A.S., and Jasim, E.Q., 2014, Synthesis, characterization and study of some tetrazole compounds as new corrosion inhibitors for C-steel in 0.5 M HCl solution, Int. J. Eng. Res., 3 (10), 613–617.
[27] Mekky, A.H., and Thamir, S.M., 2019, Synthesis, characterisation and antibacterial evaluation of some novel 1-phenyl-1H-tetrazole-5-thiol derivatives, Int. J. Res. Pharm. Sci., 10 (2), 1136–1142.
[28] Herr, R.J., 2002, 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: Medicinal chemistry and synthetic methods, Bioorg. Med. Chem., 10 (11), 3379–3393.
[29] Kadawla, M., Sinha, J., and Verma, P.K., 2018, Microwave assisted synthesis of novel 3-mercapto-4,5-disubstituted 1,2,4-triazole derivatives and evaluation of antimicrobial, antitubercular activity, Pharma Innovation J., 7 (1), 41–47.
[30] Mekkey, A.H., Malk, F.H., and Kadhim, S.H., 2020, Synthesis and optical studies of the 3,4-dimethoxy benzaldehyde [5-(2-hydroxyphenyl)-1,3,4-oxadiazol-2-yl]hydrazone metal complexes, Univ. Thi-Qar J. Sci., 7 (2), 95–100.
[31] Arshad, M., Bhat, A.R., Pokharel, S., Kim, J.E., Lee, E.J., Athar, F., and Choi, I., 2014, Synthesis, characterization and anticancer screening of some novel piperonyl-tetrazole derivatives, Eur. J. Med. Chem., 71, 229–236.
[32] Sager, A.G., and Mekky, A.H., 2020, Synthesis and characterization new liquid crystals of Schiff base using microwave radiation, Drug Invent. Today, 14 (1), 70–78.
[33] Mekky, A.H., Mohammad, Z.A.A., and Auribi, S.M., 2012, Synthesis and biological activity of monocyclic spiro azetidine-2-one, J. Educ. Pure Sci., 2 (1), 67–74.
[34] Butler, R.N., 1977, Recent advances in tetrazole chemistry, Adv. Heterocycl. Chem., 21, 323–435.
DOI: https://doi.org/10.22146/ijc.74912
Article Metrics
Abstract views : 2769
| 
views : 1398
| views : 747
Copyright (c) 2022 Indonesian Journal of Chemistry
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.