Pirimidin Halkası İçeren ONS Tridentat Schiff Baz Ligand ve Cu(II), Co(II) ve Pt(IV) Komplekslerinin Sentezi, Karakterizasyonu ve Termal Çalışmaları

Yıl 2024, Cilt: 14 Sayı: 1, 345 - 355, 01.03.2024

İbrahim Taşkın , Hatice Gamze Soğukömeroğulları , Mehmet Sönmez

https://doi.org/10.21597/jist.1325970

Öz

Bu çalışmada, N-aminopirimidin-2-tiyon ve 2-furfural'ın kondenzasyonundan türeyen ONS tridentat Schiff baz ligand ((1-(furan-2-ilmetileneamino))-4-fenil-5-benzoil-pirimidin-2-tiyon) ve Pt(IV), Co(II), Cu(II) kompleksleri sentezlendi ve NMR (sadece ligand), UV-Vis, FT-IR, manyetik duyarlılık, elementel analiz, TGA/DTA ve molar iletkenlik ile karakterize edildi. Sentezlenen bileşiklerin elektrolitik iletkenlik değerleri 0.82-5.19 µS/cm aralığında olup, bileşikler elektrolitik iletkenlik özelliğine sahip değildir. Manyetik duyarlılık ölçümleri L-Cu, L-Co ve L-Pt kompleksleri için sırasıyla 1.70 BM, 4.64 BM ve 2.48 BM olarak kaydedilmiştir. Cu(II) ve Pt(IV) kompleksleri için oktahedral geometri, Co(II) kompleksi için tetrahedral geometri önerilmiştir. Schiff baz metal komplekslerinin termal kararlılıkları incelenmiştir. Schiff baz metal komplekslerinin termal kararlılıklarının Pt>Co>Cu şeklinde olduğu görülmüştür.

Anahtar Kelimeler

Pirimidin-2-tiyon, Schiff baz, Metal kompleks, Termal çalışmalar

Synthesis, Characterization and Thermal Studies of ONS Tridentate Schiff Base Ligand and Cu(II), Co(II) and Pt(IV) Complexes Containing Pyrimidine Ring

Öz

In this study, the novel ONS tridentate Schiff base ligand ((1-(furan-2-ylmethyleneamino))-4-phenyl-5-benzoyl-pyrimidine-2-thione) and its Pt(IV), Co(II) and Cu(II) complexes were synthesized and characterized by NMR (for ligand), UV-Vis, IR, magnetic moment, elemental analysis, TGA/DTA and molar conductance. The electrolytic conductivity values of the synthesized compounds are in the range of 0.82-5.19 µS/cm, and the compounds do not have electrolytic conductivity. Magnetic susceptibility measurements were recorded as 1.70 BM, 4.64 BM and 2.48 BM for the L-Cu, L-Co and L-Pt complexes, respectively. While the Cu(II) and Pt(IV) complex exhibits an octahedral structure, the Co(II) complex exhibits a tetrahedral structure. The thermal stability of Schiff base metal complexes was investigated. The thermal stability of Schiff base metal complexes was found to be Pt>Co>Cu.

Anahtar Kelimeler

Pyrimidine-2-thione, Schiff base, Metal complexes, Thermal Studies

Kaynakça

• Abdel Hamid, A.M., & Shehta, W. (2019). Synthesis of Some Novel Furan‐tagged Thienopyrimidine Derivatives as Antibacterial Agents. Journal of Heterocyclic Chemistry, 56(2), 485-492.
• Abd El-Mageed, M.M.A., Eissa, A.A.M., Awatef, E.S.F., & Osman, E.E.A. (2021). Design and synthesis of novel furan, furo[2,3-d]pyrimidine and furo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as potential VEGFR-2 inhibitors. Bioorganic Chemistry, 116, 105336.
• Abdellatif, K.R.A., Abdelall, E.K.A., Elshemy, H.A.H., Philoppes, J.N., Hassanein, E.H.M. & Kahk, N.M. (2021). Optimization of pyrazole-based compounds with 1,2,4-triazole-3-thiol moiety as selective COX-2 inhibitors cardioprotective drug candidates: Design, synthesis, cyclooxygenase inhibition, anti-inflammatory, ulcerogenicity, cardiovascular evaluation, and molecular modeling studies. Bioorganic Chemistry, 114, 105122.
• Ahmed, Y.M. & Mohamed, G.G. (2022). Synthesis, spectral characterization, antimicrobial evaluation and molecular docking studies on new metal complexes of novel Schiff base derived from 4,6-dihydroxy-1,3-phenylenediethanone. Journal of Molecular Structure, 1256,132496.
• Akçamur, Y., Altural, B., Sarıpınar, E., Kollenz, G., Kappe, O., Peters, K., Peters, E., & Schering, H. (1988). A convenientsynthesis of functionalized 1H-Pyrimidine-2-thiones. Journal of Heterocyclic Chemistry, 25,1419-1422.
• Akçamur, Y., Altural, B., Sarıpınar, E., & Kollenz, G. (1989). Reactions of cyclic oxalyl compounds, part 29 [1]: A simple synthesis of functionalized 1H-Pyrimidines. MonatsfürChem, 120, 1015–1020.
• Amirthaganesan, K., Vadivel, T., Dhamodaran, M., & Chandraboss, V.L. (2022). In vitro antifungal studies of Ruthenium (III) complex derived from chitosan Schiff bases. Materials Today: Proceedings, 60(3), 1716-1720.
• Azam, M., Al-Resayes, S.I., Trzesowska-Kruszynska, A., Kruszynski, R., Shakeel, F., Soliman, S.M., Alam, M., Khan, M.R., & Wabaidur, S.M. (2020). Zn(II) complex derived from bidentate Schiff base ligand: Synthesis, characterization, DFT studies and evaluation of anti-inflammatory activity. Journal of Molecular Structure, 1201, 127177.
• Creaven, B.S., Duff, B., Egan, D.A., Kavanagh, K., Rosair, G., Thangella, V.R., & Walsh, M. (2010). Anticancer and antifungal activity of copper(II) complexes of quinolin-2(1H)-one-derived Schiff bases. Inorganica Chimica Acta, 363(14), 4048-4058.
• Çelik, A., Sogukomerogullari, H.G., Ozdemır, S., Yalcın, M.S., & Sönmez, M. (2018). Synthesis of complexes Co, Cu, Ni and Pd supported by “ONNO” type Schiff base ligand and their DNA cleavage, antioxidant effects and antimicrobial studies. International Journal of Chemistry and Technology, 2(1), 68-75.
• Deswal, Y., Asija, S., Dubey, A., Deswal, L., Kumar, D., Jindal, D.K., & Devi, J. (2022). Cobalt(II), nickel(II), copper(II) and zinc(II) complexes of thiadiazole based Schiff base ligands: Synthesis, structural characterization, DFT, antidiabetic and molecular docking studies. Journal of Molecular Structure, 1253,132266.
• Devi, P., Singh, K., & Kubavat, B. (2023). Synthesis, spectroscopic, quantum, thermal and kinetics, antibacterial and antifungal studies: Novel Schiff base 5-methyl-3-((5-bromosalicylidene) amino)- pyrazole and its transition metal complexes. Results in Chemistry, 5,100813.
• Dewangan, D., Nakhate, K.T., Verma, V.S., Nagori, K., & Tripathi, D.K. (2017). Synthesis, Characterization, and Screening for Analgesic and Anti‐Inflammatory Activities of Schiff Bases of 1,3,4‐Oxadiazoles Linked With Quinazolin‐4‐One. Journal of Heterocyclic Chemistry, 54(6), 3187-3194.
• El Sayed, D.S., & Abdelrehim, E.M. (2021). Computational details of molecular structure, spectroscopic properties, topological studies and SARS-Cov-2 enzyme molecular docking simulation of substituted triazolo pyrimidine thione heterocycles. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 261,120006.
• Gokulnath, G., Manikandan, R., Anitha, P., & Umarani, C. (2021). Synthesis, characterization, in vitro antimicrobial and anticancer activity of metal(II) complexes of Schiff base-derived from 3-formyl-2-mercaptoquinoline and thiosemicarbazide. Phosphorus, Sulfur, and Silicon and the Related Elements, 196(12), 1078-1083.
• Gülcan, M., & Sönmez, M. (2011). Synthesis and characterization of Cu(II), Ni(II), Co(II), Mn(II) and Cd(II) transition metal complexes of tridentate Schiff base derived from o-vanillin and N-aminopyrimidine-2-thione. Phosphorus Sulfur and Silicon, 186, 1962–1971.
• Gülcan, M., Sönmez, M., & Berber, İ. (2012). Synthesis, characterization and antimicrobial activity of a new pyrimidine Schiff base and its Cu(II), Ni(II), Co(II), Pt(II) and Pd(II) complexes. Turkish Journal of Chemistry, 36,189-200.
• Kaur, M., Kumar, S., Younis, S.A., Yusuf, M., Lee, J., Weon, S., Kim, K.H., & Malik, A.K. (2021). Post-Synthesis modification of metal-organic frameworks using Schiff base complexes for various catalytic applications. Chemical Engineering Journal, 423,130230.
• Keser Karaoğlan, G. (2022). Synthesis of new Schiff base and its Ni(II), Cu(II), Zn(II) and Co(II) complexes;photophysical, fluorescence quenching and thermal studies. Journal of Molecular Structure, 1256,132534.
• Kumari, B., Singh, K., & Sharma, A. (2022). Synthesis, crystal structure and molecular docking studies of novel Schiff base ligand 9-(((3-ethyl-5-mercapto/thio-4H-1,2,4-triazole-4-yl)imino)methyl)-anthracene and its complexes with Ni(II), Cu(II), Zn(II) and Cd(II): Comparative spectral, thermo-kinetics, radical scavenging and antimicrobial studies. Chemical Data Collections, 38,100833.
• Kwon, Y.E., Whang, K.J., Park, Y.J., & Kim, K.H. (2003). Synthesis, characterization and antitumor activity of novel octahedral Pt(IV) complexes. Bioorganic & Medicinal Chemistry, 11,1669-1676.
• Lever, A.B.P. (1980). Inorganic Electronic Spectroscopy (4th ed.) London: Elsevier.
• Mandal, S., Sarkar, M., Denrah, S., Bagchi, A., Biswas, A., Cordes, D.B., Slawin, A.M.Z., & Saha, N.C. (2023). Catalytic and anticancer activity of two new Ni(II) complexes with a pyrazole based heterocyclic Schiff-base ligand: Synthesis, spectroscopy and X-ray crystallography. Journal of Molecular Structure,1287,135648.
• Maravalli, P.B., Dhumwad, S.D., & Goudar, T.R. (1999). Synthetic, spectral, thermal and biological studies of lanthanide(III) complexes with a Schiff base derived from 3-N-Methylpiperidino-4-Amino-5-Mercapto-1,2,4-Triazole. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 29, 525-540.
• Mishra, C.B., Barodia, S.K., Prakash, A., Senthil Kumar, J.B., & Luthra, P.M. (2010). Novel 8-(furan-2-yl)-3substituted thiazolo [5,4-e][1,2,4] triazolo[1,5-c] pyrimidine-2(3H)-thione derivatives as potential adenosine A2A receptor antagonists. Bioorganic & Medicinal Chemistry,18(7), 2491-2500.
• Modi, C.K. (2009). Synthesis, spectral investigation and thermal aspects of coordination polymeric chain assemblies of some transition metal ions with bis-pyrazolones. Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy, 71,1741-1748.
• Palaniammal, A., & Vedanayaki, S. (2021). Synthesis, spectroscopic, anti microbial, anti cancer and DNA cleavage of mono nuclear bidentate Schiff base Co(II), Ni(II), Cu(II) and Zn(II) complexes obtained from (3,4-bis((E)-(1-(2- hydroxyphenyl) ethylidene)amino)(phenyl) methanone. Materials Today: Proceedings, 47(9), 1988-1998.
• Qi, J., Luo, Y., Zhou, Q., Su, G., Zhang, X., Nie, X., Lv, M., & Li, W. (2022). Synthesis, structure and anticancer studies of Cu(II) and Ni(II) complexes based on 2-hydroxy-1-naphthaldehyde-4-aminoantipyrine Schiff-base. Journal of Molecular Structure, 1255, 132458.
• Rangaswamy, V., Renuka, S., & Venda, I. (2022). Synthesis, spectral characterization and antibacterial activity of transition metal (II) complexes of tetradentate Schiff base ligand. Materials Today: Proceedings, 51(4),1810-1816.
• Salib, K.A.R., Saleh, A.A., El-Wafa, S.A., & El-Shafiy, H.F.O. (2003). Preparation and Characterization of Novel Asymmetrical Schiff-Base Ligands Derived from 2methyl-7-formyl-8-hydroxyquinoline and their Metal Complexes. Journal of Coordination Chemistry, 56(4), 283-298.
• Savir, S., Liew, J.W.K., Vythilingam, I., Lim, Y.A.L., Tan, C.H., Sim, K.S., Lee, V.S., Maah, M.J., & Tan, K.W. (2021). Nickel(II) Complexes with Polyhydroxybenzaldehyde and O,N,S tridentate Thiosemicarbazone ligands: Synthesis, Cytotoxicity, Antimalarial Activity, and Molecular Docking Studies. Journal of Molecular Structure, 1242, 130815.
• Shanty, A.A., Raghu, K.G., & Mohanan, P.V. (2019). Synthesis, characterization: Spectral and theoretical, molecular docking and in vitro studies of copper complexes with HIV RT enzyme. Journal of Molecular Structure, 1197, 154-163.
• Soğukömeroğulları, H.G., Tok Taşkın, T., Yılmaz, F., Berber, İ., & Sönmez, M. (2015). Synthesis, characterization, biological studies, and molecular modeling of mixed ligand bivalent metal complexes of Schiff bases based on N-aminopyrimidine-2-one/2-thione. Turkish Journal of Chemistry, 39(3), 497-509.
• Sogukomerogullari, H.G., Sönmez, M., & Ceyhan, G. (2019). ONO Tip Schiff Baz Komplekslerinin Sentezi, Karakterizasyonu, Katalitik Özellikleri ve Termal Çalışmaları. Süleyman Demirel Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 23(3), 701-708.
• Sogukomerogullari, H.G., Yalçın, Ş.P., Ceylan, Ü., Aytar, E., Aygün, M., Richeson, D.S., & Sönmez, M. (2019). Synthesis of Fe and Cu metal complexes derived from ‘SNS’ Pincer type ligands and their efficient catalyst precursors for the chemical fixation of CO2. Journal of Chemical Science, 131, 32-44.
• Sogukomerogullari, H.G., Taskin Tok, T., Uruş, S., & Sönmez, M. (2022). Pd (II) complexes bearing “SNS” pincer-type thioether ligands: Application as catalysts in the synthesis of vitamin K3. Applied Organometallic Chemistry, 36(1), e6467.
• Sönmez, M., & Şekerci, M. (2003). Synthesis, characterization, and thermal investigation of copper(II), nickel(II), cobalt(II), and zinc(II) complexes with 5-benzoyl-1-(phenylmethylenamino)-4-phenyl-1H-pyrimidine-2-thione. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33, 1689-1701.
• Sönmez, M., & Şekerci, M. (2007). The template synthesis, spectral characterization and thermal behaviour of new binuclear Schiff base complexes derived from N-aminopyrimidine with 2,3-butandion. Journal of the Serbian Chemical Society, 72, 259-264.
• Sönmez, M., Çelebi, M., Levent, A., Berber, İ., & Şentürk, Z. (2010). A new pyrimidine-derived ligand, Npyrimidine oxalamic acid, and its Cu (II), Co (II), Mn (II), Ni (II), Zn (II), Cd (II), and Pd (II) complexes: synthesis, characterization, electrochemical properties, and biological activity. Journal of Coordination Chemistry, 63, 848-860.
• Sönmez, M., Sogukomerogullari, H.G., Öztemel, F., & Berber, İ. (2014). Synthesis and biological evaluation of a novel ONS tridentate Schiff base bearing pyrimidine ring and some metal complexes. Medicinal Chemistry Research, 23, 3451-3457.
• Sridhar, S.K., Pandeya, S.N., Stables, J.P. & Ramesh, A. (2002). Anticonvulsant activity of hydrazones, Schiff and Mannich bases of isatin derivatives. European Journal of Pharmaceutical Science, 16, 129-132.
• Sun, Y., Lu, Y., Bian, M., Yang, Z., Ma, X., & Liu, W. (2021). Pt(II) and Au(III) complexes containing Schiff-base ligands: A promising source for antitumor treatment. European Journal of Medicinal Chemistry, 211, 113098.
• Uçan, S.Y., Uçan, M., & Mercimek, B. (2005). Synthesis and Characterization of new Schiff bases and their cobalt(II), nickel(II), copper(II), zinc(II), cadmium(II) and mercury(II) complexes. Synthesis and Reactivity in Inorganic Metal-Organic and Nano-Metal Chemistry, 35, 417-421.
• Vincent, S.G. & Joseph, J. (2021). Evaluation of antioxidant activity and antimalarial activity of flavone based tetradentate ligand and its metal complexes. Materials Today: Proceedings, 45(2), 2159-2165.
• Wang, Y.Y., Xu, F.Z., Zhu, Y.Y., Song, B., Luo, D., Yu, G., Chen, S., Xue, W., & Wu, J. (2018). Pyrazolo[3,4d]pyrimidine derivatives containing a Schiff base moiety as potential antiviral agents. Bioorganic & Medicinal Chemistry Letters, 28(17), 2979-2984.
• Wang, Y., Li, K., Xu, W., & Gou, S. (2023). Design, synthesis, and biological evaluation of a series of benzofuran[3,2-d]pyrimidine-4(3H)-one derivatives containing thiosemicarbazone analogs as novel PARP-1 inhibitors. Bioorganic Chemistry, 139, 106759.
• Yılmaz Baran, N. & Saçak, M. (2017). Synthesis, characterization and molecular weight monitoring of a novel Schiff base polymer containing phenol group: Thermal stability, conductivity and antimicrobial properties. Journal of Molecular Structure, 1146, 104-112.