NEW SCHIFF BASES DERIVED from 3,4-DIAMINO-1H-1,2,4-TRIAZOLE-5(4H)-THIONE: SYNTHESIS and CHARACTERIZATION

Abstract

A new synthetic approach has been applied to obtain a compound 3,4-diamino-1H-1,2,4-triazole-5(4H)-thione (2) by using 5-amino-1,3,4-thiadiazole-2-sulfonamide (1) and hydrazine hydrate as starting materials. New Schiff bases (3a-d) are obtained by the reaction of the compound 3,4-diamino-1H-1,2,4-triazole-5(4H)-thione (2) and varied aldehydes. The structures of the new compounds were characterized by spectral (IR, 1H and 13C NMR) and elemental analysis.

Keywords

• Thione
• Schiff base
• Sulfonamide
• Triazole
• Hydrazine hydrate

Supporting Institution

Kütahya Dumlupınar Üniversitesi, Fen-edebiyat Fakültesi

Project Number

2008-1

Thanks

This study was supported by Dumlupınar University (Grant No: 2008-1)

References

1. [1] Klimeˇsova, V., Zahajka, L., Waisser, K., Kaustova, J., M¨ollmann, U., (2004), Synthesis and antimycobacterial activity of 1,2,4-triazole 3-benzylsulfanyl derivatives, Il Farmaco, 59, 279–288.
2. [2] Zani, F., Vicini, P., Incerti, M., (2004), Synthesis and antimicrobial properties of 2-(benzylidene-amino)-benzo[d]isothiazol-3-ones, Eur. J. Med. Chem. 39, 135–40.
3. [3] Tehranchian, S., Akbarzadeh, T., Fazeli, M. R., Jamalifar, H., Shafiee, A., (2005), Synthesis and antibacterial activity of 1-[1,2,4-triazol-3-yl] and 1-[1,3,4-thiadiazol-2-yl]-3-methylthio-6,7-dihydrobenzo[c]thiophen-4(5H)ones, Bioorg. Med. Chem. Lett. 15, 1023–1025.
4. [4] Sahoo, S., Patwari, P. K., Kumar, M. C. B., Setty, C. M., (2013), Synthesis and Biological Activity of Certain Mannich Bases Derivatives from 1,2,4-Triazoles, Iranian J. Pharma. Sci., 9(4), 51–60.
5. [5] Al-Khuzaie, M. G. A., Al-Majidi, S. M. H., (2014), Synthesis, Characterization and Evaluation Antimicrobial Activity of Some New substituted 2-Mercapto-3-Phenyl-4(3H)- Quinazolinone, Iraqi J. Sci., 55(2B), 582–593..
6. [6] Mahmoud, M. R., Abou-Elmagd, W. S. I., . El-Shahawi, M. M., Hekal, M. H., (2014), Novel Fused and Spiro Heterocyclic Compounds Derived from 4-(4-Amino-5-mercapto-4H1,2,4-triazol-3-yl)phthalazin-1(2H)-one, Eur. Chem. Bull., 3(7), 723–728.
7. [7] Hanif, M., Saleem, M., Hussain, M. T., Rama, N. H., Zaib, S., Aslam, M. A. M., Jones, P. G., Iqbal, J., (2012), Synthesis, Urease Inhibition, Antioxidant and Antibacterial Studies of Some 4-Amino-5-aryl-3H-1,2,4-triazole-3- thiones and Their 3,6-Disubstituted 1,2,4-Triazolo[3,4- b]1,3,4-thiadiazole Derivatives, J. Braz. Chem. Soc., 23(5), 854–860.
8. [8] Hope, W. W., Lewis, R., Smith, J. A., (2010), Clinical Primer: Potential Hepatic Complications with Triazole Therapy, USA: University of Wisconsin-Madison School of Medicine and Public Health, School of Pharmacy, and School of Nursing and Fallon Medica LLC.

9. [9] Boraei, A. T. A., Singh, P. K., Sechi, M., Satta, S., (2019), Discovery of novel functionalized 1,2,4-triazoles as PARP-1 inhibitors in breast cancer: Design, synthesis and antitumor activity evaluation. Eur. J. Med. Chem., 182, 111621.
10. [10] Arul, K., Smith, A. A., (2014), In-Silico Design, Synthesis and in vitro Anticancer Evaluation of Some Novel 1,2,4- Triazole Derivatives, The Experiment, 21(1), 1439–1452.
11. [11] El-Sherief, H. A. M., Youssif, B. G. M., Abbas Bukhari, S. N., Abdelazeem, A. H., Abdel-Aziz, M., Abdel-Rahman, H. M., (2018), Synthesis, anticancer activity and molecular modeling studies of 1,2,4-triazole derivatives as EGFR inhibitors. Eur. J. Med. Chem., 156, 774–789.
12. [12] Meenaxi, M. M., Ainapure, R. Patil, P. B., Bhat, A. R., (2011), Triazolone and Their Derivatives for Anti-Tubercular Activities, Asian J. Res. Chem., 4(7), 1050–1054.
13. [13] Abdul Hameed, A., Hassan, F., (2014), Synthesis, Characterization and Antioxidant Activity of Some 4- Amino-5-phenyl-4H-1,2,4-triazole-3-thiol Derivatives, Int. J. App. Sci. Tech., 4 (2), 202–211.
14. [14] Jess, S., Kildea, S., Moody, A., Rennick, G., Murchie, A. K., Cooke, L. R., (2014), European Union policy on pesticides: implications for agriculture in Ireland. Pest Management Science, 70(11), 1646–1654.
15. [15] Abdullah, H. M., Jassim, I. K., Safi, M. N., (2012), Synthesis and Characterization of New Heterocyclic Compounds with Studying Its Biological Activity, Kerbala J. Pharm. Sci., 4, 115-135.
16. [16] Pandey, V. K., Tusi, Z., Tusi, S., Joshi, M., (2012), Synthesis and Biological Evaluation of Some Novel 5-[(3-Aralkyl amido/imidoalkyl)phenyl]-1,2,4-triazolo [3,4-b]-1,3,4- thiadiazines as Antiviral Agents, ISRN Org. Chem., 1-7.
17. [17] Mustafa, M., Anwar, S., Elgamal, F., Ahmed, E. R., Aly, O. M., (2019), Potent combretastatin A-4 analogs containing 1,2,4-triazole: Synthesis, antiproliferative, anti-tubulin activity, and docking study. Eur. J. Med. Chem., 183, 111697.
18. [18] Mustafa, M., Abdelhamid, D., Abdelhafez, E. S. M. N., Ibrahim, M. A. A., Gamal-Eldeen, A. M., Aly, O. M., (2017), Synthesis, antiproliferative, anti-tubulin activity, and docking study of new 1,2,4-triazoles as potential combretastatin analogues Eur. J. Med. Chem., 141, 293–305.
19. [19] Mousa, M. N., Al-jadaan, S. A. N.,( 2012), Evaluation of the Anti-Inflammatory Activity and Ulcerogenic Liability of 5-(3-Chloro-1-benzothien-2-yl)-4-phenyl-4H-1,2,4- triazole-3-thiol, Bas. J. Vet. Res., 11(1), 122-127.
20. [20] Kavakli, C., Kavakli, P. A., Güven, O., (2014), Preparation and Characterization of Glycidyl Methylacrylate Grafted 4- Amino-1,2,4-triazole Modified Nonwoven Fiber Absorbent for Environmental Application, Rad. Phys. Chem., 94, 111-114.
21. [21] Hassan, F. A., Younus, K. W., (2012), Biological Evaluation of Some Azole Derivatives in Cooling Fluids (Lubricant Oils), Res. J. Bio. Sci., 7(1), 48-51.
22. [22] Sripriya1, S., Subha, C., Selvaraj, A., (2013), The Inhibition Chemistry of 2-Amino, 5-Phenyl 1, 3, 4-Triazole for Aluminium in Hydrochloric Acid Solution, IOSRJAC, 6(2), 25-29.
23. [23] Shukla, P. K., Soni, N., Verma, A., Jha, A. K., (2014), Synthesis, Characterization and in vitro Biological Evaluation of A Series of 1,2,4-Triazoles Derivatives & Triazole Based Schiff Bases, Der Pharma Chemica, 6 (3), 153- 160.
24. [24] Sun, S., Lou, H., Gao, Y., Fan, P., Ma, B., Ge, W., Wang, X., (2004), Liquid chromatography–tandem mass spectrometric method for the analysis of fluconazole and evaluation of the impact of phenolic compounds on the concentration of fluconazole in Candida albicans. J. Pharmöl and Biomed Anal., 34(5), 1117–1124.
25. [25] Clemons, M., Coleman, R., Verma, S., (2004), Aromatase inhibitors in the adjuvant setting: bringing the gold to a standard?, Cancer Treatment Reviews, 30(4), 325–332.
26. [26] Johnston, G., (2002), Medicinal Chemistry and Molecular Pharmacology of GABA-C Receptors. Curr. Top. Med.. Chem., 2(8), 903–913.
27. [27] Grivani, G., Tahmasebi, V., Eskandari, K., Khalaji, A. D., Bruno, G., & Rudbari, H. A. (2013). Synthesis, characterization, crystal structure determination and computational study of the two new bidentate O, N Schiff bases derived from bromosalicylaldehyde and amines containing alkyl halide pendant groups. J. Mol. Struct., 1054-1055, 100–106.
28. [28] Przybylski, P., Huczynski, A., Pyta, K., Brzezinski, B., Bartl, F., (2009), Biological Properties of Schiff Bases and Azo Derivatives of Phenols. Curr. Org. Chem., 13(2), 124–148.
29. [29] Wu, S., Zhang, W., Qi, L., Ren, Y., Ma, H., (2019), Investigation on 4-amino-5-substituent-1,2,4-triazole-3-thione Schiff bases an antifungal drug by characterization (spectroscopic, XRD), biological activities, molecular docking studies and electrostatic potential (ESP). J. Mol. Struct., 1197, 171-182.
30. [30] Bekircan, O., Bektas, H., (2006), Synthesis of New Bis-1,2,4-Triazole Derivatives. Molecules, 11(6), 469–477.
31. [31] Potts, K. T., Huseby, R. M., (1966), 1,2,4-Triazoles. XVI. Derivatives of the s-Triazolo[3,4-b][1,3,4]thiadiazole Ring System1. J. Org. Chem., 31(11), 3528–3531.
32. [32] Eweiss, N. F., Bahajaj, A. A., Elsherbini, E. A., (1986). Synthesis of heterocycles. PartVI. Synthesis and antimicrobial activity of some 4-amino-5-aryl-1,2,4-triazole-3-thiones and their derivatives. J. Heterocyclic. Chem., 23(5), 1451–1458.
33. [33] George, T., Mehta, D. V., Tahilramani, R., David, J., Talwalker, P. K., (1971), Synthesis of some s-triazoles with potential analgesic and antiinflammatory activities. J. Med. Chem., 14(4), 335–338.
34. [34] Bhalerao, U. T., Muralikrishna, C., Rani, B. R., (1994), Laccase enzyme catalysed efficient synthesis of 3-Substituted-1,2,4-triazoto(4,3-b)(4,1,2)benzothiadiazine-8-ones. Tetrahedron, 50(13), 4019–4024.
35. [35] Invidiata, F. P., Furná, G., Lampronti, I., Simoni, D., (1997), 1,2,4-Triazoles. Improved synthesis of 5-substituted 4-amino-3-mer-cato-(4H)-1,2,4-triazoles and a facile route to 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. J. Heterocyclic Chem., 34(4), 1255–1258.
36. [36] Cartwright, D. D. J., Clark, B. A. J., McNab, H., (2001), Gas-phase pyrolysis of 4-amino-3-allylthio-1,2,4-triazoles: a new route to [1,3]thiazolo[3,2-b][1,2,4]triazoles, J. Chem. Soc. Perkin Trans, 1, 424.
37. [37] Vainilavicius, P., Smicius, R., Jakubkiene, V., Tumkevicius, S., (2001), Synthesis of 5-(6-Methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-4-amino-1,2,4-triazole-3-thione and its Reactions with Polyfunctional Electrophiles. Monatshefte Fuer Chemie/Chemical Monthly, 132(7), 825–831.
38. [38] Shaker, R. M., & Aly, A. A. (2006). Recent Trends in the Chemistry of 4-Amino-1,2,4-triazole-3-thiones. Phosphorus, Sulfur, Silicon Relat Elem., 181(11), 2577–2613.
39. [39] Hoggarth, E. J. Chem. Soc. 1952, 4817.
40. [40] Ali, T. E.-S. (2009). Utility of thiocarbohydrazide in heterocyclic synthesis. J. Sulfur Chem., 30(6), 611-647.
41. [41] Bülbül, M., Kasimoğullari, R., Küfrevioğlu, Ö. I., (2008), Amide derivatives with pyrazole carboxylic acids of 5-amino-1,3,4-thiadiazole 2-sulfonamide as new carbonic anhydrase inhibitors: Synthesis and investigation of inhibitory effects. J. Enzyme. Inhib. Med. Chem., 23(6), 895–900.
42. [42] Kumar, M. S., Kumar, S. L. A., Sreekanth, A., Anticorrosion Potential of 4-Amino-3-methyl-1,2,4-triazole-5-thione Derivatives (SAMTT and DBAMTT) on Mild Steel in Hydrochloric Acid Solution. Ind. Engineer. Chem. Res, 51(15), 5408–5418, (2012).
43. [43] Shneine, J. K, Alaraji, Y. H, (2014), Chemistry of 1, 2, 4-Triazole: A Review Article, Int. J. Sci. Res., 5: 1411-1423..
44. [44] Subashchandrabose, S., Krishnan, A. R., Saleem, H., Thanikachalam, V., Manikandan, G., Erdogdu, Y., (2010), FT-IR, FT-Raman, NMR spectral analysis and theoretical NBO, HOMO–LUMO analysis of bis(4-amino-5-mercapto-1,2,4-triazol-3-yl)ethane by ab initio HF and DFT methods. J. Mol. Struct., 981(1-3), 59–70.
45. [45] Krishnakumar, V., Xavier, R. J., (2004), FT Raman and FT–IR spectral studies of 3-mercapto-1,2,4-triazole. Spectrochim. Acta A Mol. Biomol. Spectrosc., 60(3), 709–714.
46. [46] Bahgat, K., Fraihat, S., (2015), 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., 135, 1145–1155.
47. [47] Snehalatha, M., Ravikumar, C., Hubert Joe, I., Sekar, N., Jayakumar, V. S., (2009), Spectroscopic analysis and DFT calculations of a food additive Carmoisine. Spectrochim. Acta A Mol. Biomol. Spectrosc., 72(3), 654–662.
48. [48] Zamani, K., Faghihi, K., Sangi, M. R., Zolgharnein, (2003), Synthesis of Some New Substituted 1,2,4-Triazole and 1,3,4-Thiadiazole and Their Derivatives, Turk. J. Chem. 27, 119-126.
49. [49] Mohamed, G. G., Omar, M. M., Hindy, A. M. M., (2005), Synthesis, characterization and biological activity of some transition metals with Schiff base derived from 2-thiophene carboxaldehyde and aminobenzoic acid. Spectrochim. Acta A Mol. Biomol. Spectrosc., 62(4-5), 1140–1150.
50. [50] Bagihallia, G.B., Patila, S.A., Badamib, P.S., (2009), Synthesis, Physicochemical Investigation and Biological Studies of Zinc(II) Complexes with 1,2,4-Triazole Schiff Bases, J. Iran. Chem. Soc., 6(2), 259-270.
51. [51] Joshi, R., Kumari, A., Singh, K., Mishra, H., & Pokharia, S. (2020). Triorganotin(IV) complexes of Schiff base derived from 1,2,4-triazole moiety: Synthesis, spectroscopic investigation, DFT studies, antifungal activity and molecular docking studies. Journal of Molecular Structure, 127639.
52. [52] Rafiq, M., Saleem, M., Hanif, M., Kang, S. K., Seo, S.-Y., Lee, K. H., (2015), Synthesis, structural elucidation and bioevaluation of 4-amino-1,2,4-triazole-3-thione’s Schiff base derivatives. Arch. Pharm. Res., 39(2), 161–171.