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

Year 2022, Issue: 048, 25 - 41, 31.03.2022

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.

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

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Year 2022, Issue: 048, 25 - 41, 31.03.2022

Abstract

Project Number

2008-1

References

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  • [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.
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  • [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] 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] 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.
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  • [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.
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  • [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.
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  • [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] 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] 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] 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] 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] 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] 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] 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] 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] 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] 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] Johnston, G., (2002), Medicinal Chemistry and Molecular Pharmacology of GABA-C Receptors. Curr. Top. Med.. Chem., 2(8), 903–913.
  • [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] 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] 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] Bekircan, O., Bektas, H., (2006), Synthesis of New Bis-1,2,4-Triazole Derivatives. Molecules, 11(6), 469–477.
  • [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.
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  • [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] 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] 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] 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] 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.
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Details

Primary Language English
Journal Section Research Articles
Authors

Bülent Büyükkıdan 0000-0001-9619-3246

Nurgün Büyükkıdan 0000-0001-6879-9355

Aslı Atar 0000-0003-0708-8845

Project Number 2008-1
Publication Date March 31, 2022
Submission Date October 30, 2021
Published in Issue Year 2022 Issue: 048

Cite

IEEE B. Büyükkıdan, N. Büyükkıdan, and A. Atar, “NEW SCHIFF BASES DERIVED from 3,4-DIAMINO-1H-1,2,4-TRIAZOLE-5(4H)-THIONE: SYNTHESIS and CHARACTERIZATION”, JSR-A, no. 048, pp. 25–41, March 2022.