Synthesis, Characterization & Biological Survey of Novel 1,2,4-Triazole Schiff Base Derivatives

  • Zuhair M. Hassoon Directorate of Education in Thi-Qar, Ministry of Education, Iraq
  • Israa A. Alkhayyat Department of Chemistry, College of Science, Thi-Qar University, Iraq
  • Ahmed M. I. Alsanafi Directorate of Education in Thi-Qar, Ministry of Education, Iraq
  • Ibrahim A. Flifel Department of Chemistry, College of Science, Thi-Qar University, Iraq
Keywords: heterocyclic, triazole, antibacterial, ligand, complex, properties, electrostatic

Abstract

In the present study, a new ligand, 4-{[(1E)-1-(2-hydroxy-5-methyl-3 nitrophenyl) ethylidene]amino}-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (L)  and synthesis   of   iron (III),  copper (II) and  red copper (III) complexes. By using techniques including FT-IR, 1H-NMR, mass, molar conductivity, and magnetic susceptibility, the ligand and its complexes were verified to be real. Researchers looked into the compounds' antibacterial activities against the Gram-positive and Gram-negative bacterial strains of Staphylococcus aureus and Pseudomonas aeruginosa. The ligand's bioavailability investigations and its complexes showed good results compared to a standard antibiotic (ampicillin). Theoretical calculations were performed using the Hyperchem program and the electrostatic potential was studied using a semiempirical approach, which provided good information about the location of the complex. In addition, the stabilization energies of the complexes were studied. Based on the magnetic susceptibility and molar conductivity results, for the Cr(III) and Fe(III) complexes, we suggest an octahedral geometry, and for the Cu(II) complex, a tetrahedral geometry.

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References

Y. D. Kulkarni and A. Rowhani, "Synthesis of 5-(3, 5-Dinitrophenyl)-3-((Substituted-Amino) Methyl)-1, 3, 4-Oxadiazole-2 (3H)-Thione as Potential Biological Active Agents," ChemInform, vol. 21, no. 6, pp. no-no, 1990.

K. Obi, A. Kojima, H. Fukuda, and K. Hirai, "Synthesis and Biological Activity of a Novel Class of Cephalosporins With a Oxadiazolyl Hydroxypyridone Moiety at C-7," Bioorganic & Medicinal Chemistry Letters, vol. 5, no. 23, pp. 2777-2782, 1995.

M. D. Mullican, M. W. Wilson, D. T. Conner, C. R. Kostlan, D. J. Schrier, and R. D. Dyer, "Design of 5-(3, 5-di-tert-butyl-4-hydroxyphenyl)-1, 3, 4-Thiadiazoles, -1, 3, 4-Oxadiazoles, and -1, 2, 4-Triazoles as Orally Active, Nonulcerogenic Antiinflammatory Agents," Journal of Medicinal Chemistry, vol. 36, no. 8, pp. 1090-1099, 1993.

B. Tozcoparan, B. N. Gokhan, G. Aktay, E. Yesilada, and M. Ertan, "6-Benzylidenethiazolo[3,2-b]-1,2,4-Triazole-5(6H)-Ones Substituted With Ibuprofen: Synthesis, Characterization and Evaluation of Anti-Inflammatory Activity," European Journal of Medicinal Chemistry, vol. 35, no. 7-8, pp. 743–750, 2000.

B. Tozkoparan, E. Küpeli, E. Yeşilada, and M. Ertan, "Preparation of 5-Aryl-3-Alkylthio-l, 2, 4-Triazoles and Corresponding Sulfones With Antiinflammatory–Analgesic Activity," Bioorganic & Medicinal Chemistry, vol. 15, no. 4, pp. 1808-1814, 2007.

K. Sancak, Y. Ünver, D. Ünlüer, E. Düğdü, G. Kör, F. Celik, and E. Birinci, "Synthesis, Characterization, and Antioxidant Activities of New Trisubstituted Triazoles," Turkish Journal of Chemistry, vol. 36, no. 3, pp. 457-466, 2012.

Y. Ünver, K. Sancak, F. Çelik, E. Birinci, M. Küçük, S. Soylu, and N. A. Burnaz, "New Thiophene-1, 2, 4-Triazole-5(3)-Ones: Highly Bioactive Thiosemicarbazides, Structures of Schiff Bases and Triazole–Thiols," European Journal of Medicinal Chemistry, vol. 84, pp. 639-650, 2014.

J. M. Kane, M. W. Dudley, S. M. Sorensen, and F. P. Miller, "2, 4-Dihydro-3H-1, 2, 4-Triazole-3-Thiones as Potential Antidepressant Agents," Journal of Medicinal Chemistry, vol. 31, no. 6, pp. 1253-1258, 1988.

K. Shalini, N. Kumar, S. Drabu, and P. K. Sharma, "Advances in Synthetic Approach to and Antifungal Activity of Triazoles," Beilstein Journal of Organic Chemistry, vol. 7, no. 1, pp. 668-677, 2011.

R. G. Harrison, W. B. Jamieson, W. J. Ross, and J. C. Saunders, "U.S. Patent No. 4,089,962," U.S. Patent and Trademark Office, Washington, DC, 1978.

I. Küçükgüzel, E. Tatar, Ş. G. Küçükgüzel, S. Rollas, and E. De Clercq, "Synthesis of Some Novel Thiourea Derivatives Obtained From 5-[(4-Aminophenoxy) Methyl]-4-Alkyl/Aryl-2, 4-Dihydro-3H-1, 2, 4-Triazole-3-Thiones and Evaluation as Antiviral/Anti-HIV and Anti-Tuberculosis Agents," European Journal of Medicinal Chemistry, vol. 43, no. 2, pp. 381-392, 2008.

R. W. Sidwell, J. H. Huffman, G. P. Khare, B. Allen, R. J. T. Witkowski, and K. Robins, "Broad-Spectrum Antiviral Activity of Virazole: 1-β-D-Ribofuranosyl-1, 2, 4-Triazole-3-Carboxamide," Science, vol. 177, no. 4050, pp. 705-706, 1972.

B. S. Holla, B. Veerendra, M. K. Shivananda, and B. Poojary, "Synthesis, Characterization and Anticancer Activity Studies on Some Mannich Bases Derived From 1, 2, 4-Triazoles," European Journal of Medicinal Chemistry, vol. 38, no. 7-8, pp. 759-767, 2003.

E. Palaska, G. Şahin, P. Kelicen, N. T. Durlu, and G. Altinok, "Synthesis and Anti-Inflammatory Activity of 1-Acylthiosemicarbazides, 1, 3, 4-Oxadiazoles, 1, 3, 4-Thiadiazoles and 1, 2, 4-Triazole-3-Thiones," Il Farmaco, vol. 57, no. 2, pp. 101-107, 2002.

A. Almasirad, S. A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi, and A. Shafiee, "Synthesis and Anticonvulsant Activity of New 2-Substituted-5-[2-(2-Fluorophenoxy) Phenyl]-1, 3, 4-Oxadiazoles and 1, 2, 4-Triazoles," Bioorganic & Medicinal Chemistry Letters, vol. 14, no. 24, pp. 6057-6059, 2004.

U. Salgın-Gökşen, N. Gökhan-Kelekçi, Ö. Göktaş, Y. Köysal, E. Kılıç, Ş. Işık, et al., "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 & Medicinal Chemistry, vol. 15, no. 17, pp. 5738-5751, 2007.

R. A. Fletcher, A. Gilley, N. Sankhla, and T. D. Davis, "Triazoles as Plant Growth Regulators and Stress Protectants," Horticultural Reviews, vol. 24, pp. 55-138, 2000.

G. M. Sheldrick, "SHELXS 86, Program for Crystal Structure Determination," University of Göttingen, 1986.

N. Marubayashi, T. Ogawa, M. Moriwaki, and M. Haratake, "Atropisomerism in 4-(2-Thienyl)-4H-1, 2, 4-Triazole Derivatives," Chemical and Pharmaceutical Bulletin, vol. 40, no. 1, pp. 220-223, 1992.

N. Singhal, P. K. Sharma, N. Kumar, and R. Dudhe, "Potential Triazole Derivatives Having Significant Antiepileptic Effect: A Review," Mini Reviews in Medicinal Chemistry, 2012.

T. Sugane, T. Tobe, W. Hamaguchi, I. Shimada, K. Maeno, J. Miyata, et al., "Atropisomeric 4-Phenyl-4H-1, 2, 4-Triazoles: Synthesis, Chiral Resolution, and Mechanism of P-Glycoprotein Inhibition," Journal of Medicinal Chemistry, vol. 42, no. 16, pp. 3215-3226, 1999.

S. Maddila, R. Pagadala, and S. B. Jonnalagadda, "1, 2, 4-Triazoles: A Review of Synthetic Approaches and the Biological Activity," Letters in Organic Chemistry, vol. 10, no. 10, pp. 693-714, 2013.

S. Hester, T. Moore, W. T. Padgett, L. Murphy, C. E. Wood, and S. Nesnow, "The Hepatocarcinogenic Conazoles: Cyproconazole, Epoxiconazole, and Propiconazole Induce a Common Set of Toxicological and Transcriptional Responses," Toxicological Sciences, vol. 127, no. 1, pp. 54-65, 2012.

I. Küçükgüzel, Ş. G. Küçükgüzel, S. Rollas, G. Ötük-Sanış, O. Özdemir, I. Bayrak, et al., "Synthesis of Some 3-(Arylalkylthio)-4-Alkyl/Aryl-5-(4-Aminophenyl)-4H-1, 2, 4-Triazole Derivatives and Their Anticonvulsant Activity," Il Farmaco, vol. 59, no. 11, pp. 893-901, 2004.

T. Plech, M. Wujec, U. Kosikowska, A. Malm, B. Rajtar, and M. Polz-Dacewicz, "Synthesis and In Vitro Activity of 1, 2, 4-Triazole-Ciprofloxacin Hybrids Against Drug-Susceptible and Drug-Resistant Bacteria," European Journal of Medicinal Chemistry, vol. 60, pp. 128-134, 2013.

I. Khan, A. Ibrar, and N. Abbas, "Triazolothiadiazoles and Triazolothiadiazines – Biologically Attractive Scaffolds," European Journal of Medicinal Chemistry, vol. 63, pp. 854-868, 2013.

Küçükgüzel, Ş. G. Küçükgüzel, S. Rollas, and M. Kiraz, "Some 3-Thioxo/Alkylthio-1, 2, 4-Triazoles With a Substituted Thiourea Moiety as Possible Antimycobacterials," Bioorganic & Medicinal Chemistry Letters, vol. 11, no. 13, pp. 1703-1707, 2001.

K. Jassim, A. A. Fayad, and W. K. Jassim, "Study on the Synthesis and Properties of Benzimidazole Derivatives," Kufa Journal of Pharmaceutical Sciences, vol. 2, no. 2, pp. 228-240, 2011.

P. Kaur, R. Kaur, and M. Goswami, "A Review on Methods of Synthesis of 1, 2, 4-Triazole Derivatives," International Research Journal of Pharmacy (IRJP), vol. 9, pp. 1-35, 2018.

M. E. Kodadi, M. Benamar, B. Ibrahim, A. Zyad, F. Malek, R. Touzani, et al., "New Synthesis of Two Tridentate Bipyrazolic Compounds and Their Cytotoxic Activity Against Tumor Cell Lines," Natural Product Research, vol. 21, no. 11, pp. 947-952, 2007.

H. Singh, K. N. Shukla, R. Dwivedi, and L. D. Yadav, "Synthesis of Some New Heterocyclic Compounds Containing Bridgehead Nitrogen Atom as Antifungal Drugs," Indian Journal of Pharmaceutical Sciences, vol. 50, no. 1, 1988.

G. Manjunath, G. Bheemaraju, M. Mahesh, and P. V. Ramana, "Synthesis of New 5-((2-(Substituted Phenoxymethyl)-1H-Benzo[d]imidazol-1-yl) Methyl)-1, 3, 4-Oxadiazole-2-Thiol: A Novel Class of Potential Antibacterial and Antifungal Agents," Annales Pharmaceutiques Françaises, vol. 73, no. 6, pp. 452-460, 2015.

M. Hanif and Z. H. Chohan, "Design, Spectral Characterization and Biological Studies of Transition Metal (II) Complexes With Triazole Schiff Bases," Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, vol. 104, pp. 468-476, 2013.

Z. Hassoon and I. Flifel, "Synthesis, Characterization and Antioxidant Study of New 2-({2-[5-(2-Hydroxyphenyl)-1, 3, 4-Oxadiazol-2-yl] Hydrazinylidene} Methyl)-4-Methoxyphenol and Their Transition Metal Complexes," Turkish Journal of Physiotherapy and Rehabilitation, vol. 32, no. 3, pp. 17144-17158, 2021.

A. M. Alsanafi and I. A. Flifel, "Syntheses, Characterization of a New Legend 2-Hydroxy-N'-(5-Phenyl-1, 3, 4-Oxadiazol-2-yl) Benzohydrazide With Some Transition Metal Complexes," Annals of the Romanian Society for Cell Biology, vol. 25, no. 6, pp. 18167-18182, 2021.

Published
2024-09-21
How to Cite
Hassoon, Z. M., Alkhayyat, I. A., Alsanafi, A. M. I., & Flifel, I. A. (2024). Synthesis, Characterization & Biological Survey of Novel 1,2,4-Triazole Schiff Base Derivatives. Central Asian Journal of Theoretical and Applied Science, 5(5), 469-482. Retrieved from https://cajotas.centralasianstudies.org/index.php/CAJOTAS/article/view/1496
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