Synthesis, characterization, and biological evaluation of new copper complexes of naphthyl pyrazole ligands

Synthesis, characterization, and biological evaluation of new copper complexes of naphthyl pyrazole ligands

Two naphthalene pyrazole ligands were synthesized using KOH/DMSO and Cu catalyst and characterized with FT-IR, ESIMS, $^{1} H, and ^{13}C NMR$ spectroscopies. The crystal structures of 1-(2-methylnaphthalen-1-yl)-1H-pyrazole (MeNap-Pz) ligand have been determined with X-ray crystal structure analysis. Reaction of the ligands with $Cu(NO_3 )_2 x3.5H_2O$ gave two new complexes and characterized with magnetic susceptibility, molar conductance, FT-IR, LCMS-MS, ICP-OES, NMR, thermogravimetric analysis, and ESR spectra. The spectral data of the ligands are coordinated to the metal ion through the nitrogen atoms of the pyrazole ring. Consequently, it has been determined that [Cu(MeNap-$Pz)^2 (NO^3 )]NO^3 .2H^2O$ complex showed square planar geometry and [Cu(NapMe-$Pz)2 (NO3 )2 ]. H2O$ complex showed octahedral geometry. All compounds were screened for in vitro antibacterial activity and copper complexes have been shown to be effective on bacteria.

___

  • 1. Cano M, Heras JV, Maeso M, Alvaro M, Ferfindez R et al. 3-[4-Phenoxyphenyl]pyrazole (Hpzpp) and 3-[4-butoxyphenyl]pyrazole (Upzbp) in rhodium chemistry. Crystal structures of 3-[4-phenoxyphenyl]pyrazole, [Rh(μ-pzpp)$(COD)]_2.1/2CH_2Cl_2$ and [Rh(μ-pzbp)(COD)]2. Journal of Organometallic Chemistry 1997; 534: 159-172. doi: 10.1016/S0022-328X(96)06890-8
  • 2. Chauhan A, Sharma PK, Kaushik N. Pyrazole: a versatile moiety. International Journal of ChemTech Research 2011; 3 (1): 11-17.
  • 3. Hamed MA, El Gokha AA, Abdelwahed RER, Mohamed AA, El-Torgoman AM et al. Synthesis and biological evaluation of some new pyrazole derivatives. International Journal of Pharmaceutical Science and Research 2016; 1 (5): 4414-4421. doi: 10.13040/ IJPSR.0975-8232.7(11).4414-21
  • 4. Kane JL, Hirth BH, Liang B, Gourlie BB, Nahill S et al. Ureas of 5-Aminopyrazole and 2-Aminothiazole Inhibit Growth of Gram-Positive Bacteria. Bioorganic & Medicinal Chemistry Letters 2003; 13 (24): 4463–4466. doi.org/10.1016/j.bmcl.2003.09.013
  • 5. Malhotra P, Pattan S, Nikalje A. Microwave assisted synthesis and antiinflammatory activity of 3,5-diaryl substituted–2-pyrazolines. Journal of Pharmacy and Pharmaceutical Sciences 2010; 2 (2): 21-26.
  • 6. Addel-Aziz HA, El-Zahabi HAS, Dawood KM. Microwave-assisted synthesis and In-vitro anti-tumor activity of 1,3,4-Triaryl-5-Narylpyrazole-carboxamides. European Journal of Medicinal Chemistry 2010; 45: 2427-2432. doi: 10.1016/j.ejmech.2010.02.026
  • 7. Elgemeie GH, Zaghary WA, Amin KM, Nasr TM. New trends in synthesis of pyrazole nucleosides as new antimetabolites. Nucleosides, Nucleotides, and Nucleic Acid 2005; 24 (8): 1227-1247. doi: 10.1081/NCN-200067421
  • 8. Kobayashi K, Uchiyama M, Ito H, Takahashi, H, Yoshizumi T et al. Discovery of novel arylpyrazole series as potent and selective opioid receptor-like 1 (ORL1) antagonists. Bioorganic Medicinal Chemistry Letters 2009; 19 (13): 3627-3631. doi: 10.1016/j.bmcl.2009.04.116
  • 9. Lamberth C. Pyrazole chemistry in crop protection. Heterocycles 2007; 71 (7): 1467-1502. doi: 10.3987/REV-07-613
  • 10. Jana A, Brandão P, Jana H, Jana AD, Mondal G et al. Synthesis, structure and catalytic promiscuity of a napthyl-pyrazole Mn(II) complex and structure-activity relationships. Journal of Coordination Chemistry 2019; 72 (16): 2636-2653. doi: 10.1080/00958972.2019.1658192
  • 11. Weekes RJ, Hawes CS. Synthesis, coordination chemistry and photophysical properties of naphtho-fused pyrazole ligands. CrystEngComm 2019; 21: 5152-5163. doi: 10.1039/C9CE01074B.
  • 12. Ali SA, Awad SM, Said AM, Mahgoub S, Taha H et al. Design, synthesis, molecular modelling and biological evaluation of novel 3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives as potent antioxidants and 15-Lipoxygenase inhibitors. Journal of Enzyme Inhibition and Medicinal Chemistry 2020; 35 (1): 847-863. doi: 10.1080/14756366.2020.1742116J.
  • 13. He L, Duan L, Oiao J, Zhang D, Wang L et al. Enhanced stability of blue-green light-emitting electrochemical cells based on a cationic iridium complex with 2-(1-phenyl-1H-pyrazol-3-yl)pyridine as the ancillary ligand. Chemical Communications 2011; 47: 6467-6469. doi: 10.1039/ C1CC11263E
  • 14. Montoya V, Pons J, Solans X, Font-Bardia M, Ros J. Synthesis and characterisation of new N1-alkyl-3,5-dipyridylpyrazole derived ligands. Study of their reactivity with Pd(II) and Pt(II). Inorganica Chimica Acta 2005; 358: 2763-2769. doi: 10.1016/j.ica.2005.01.028
  • 15. Prakash O, Kumar R, Sehrawat R. Synthesis and antibacterial activity of some new 2,3-dimethoxy-3-hydroxy-2-(1-phenyl-3-aryl-4-pyrazolyl) chromanones. European Journal of Medicinal Chemistry 2009; 44: 1763-1767. doi: 10.1016/j.ejmech.2008.03.028
  • 16. Bouabdallah I, Touzani R, Zidane I, Ramdani A, Radi S. Synthesis of some 1-aryl-3,5-disubstituted-pyrazoles by N-arylation of 3,5-disubstituted-pyrazoles with 4-fluoro and 2-fluoronitrobenzene under microwave irradiation and classical heating. Arkivoc 2006; 12: 138-144. doi: 10.3998/ark.5550190.0007.c16
  • 17. Monnier F, Taillefer MA. Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions. Angewandte Chemie International Edition 2009; 48: 6954-6971. doi: 10.1002/anie.200804497
  • 18. Wolf JP, Tomori H, Sadighi JP, Yin J, Buchwald SLJ. Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates. Journal of Organic Chemistry 2000; 65 (4): 1158-1174. doi: 10.1021/jo991699y
  • 19. Xu ZL, Li HX, Ren ZG, Du WY, Xu WC et al. $Cu(OAc)_2·H_2O$-catalyzed N-arylation of nitrogen-containing heterocycles. Tetrahedron 2011; 67 (29) 5282-5288. doi: 10.1016/j.tet.2011.05.025
  • 20. Suh J, Kang HS, Kim JE, Yum EK. Diversification of pyrazoles by microwave-assisted ligand free copper catalyzed N-arylation. Bulletin Korean Chemical Society 2012; 33 (6): 2067-2070. doi: 10.5012/bkcs.2012.33.6.2067
  • 21. Sugaya T, Mimury Y, Ikuta M, Mimury T, Kasai M et al. Synthesis of a 6H-Pyrazolo[4,5,1-de]acridin-6-one derivative: A useful intermediate of antitumour agents. Synthesis 1994; 1: 73-76. doi: 10.1055/s-1994-25408
  • 22. Park KH, Cho SY, Kim SS, Yum EK, Yu CM et al. Novel migration of aryl group in 3-trifluoromethylpyrazolyl aryl ether. Bulletin Korean Chemical Society 1995; 16: 799-801.
  • 23. Roy S, Roy S, Gribble GW (2012) Metalation of Pyrazoles and Indazoles. In: Gribble G (editor). Metalation of Azoles and Related FiveMembered Ring Heterocycles. Topics in Heterocyclic Chemistry, vol 29. Berlin, Heidelberg, Germany: Springer, doi: 10.1007/7081_2012_82
  • 24. Chen R, Liu CS, Zhang H, Guo Y, Bu XH et al. Three new Cu(II) and Cd(II) complexes with 3-(2-pyridyl)pyrazole-based ligand: Syntheses, crystal structures, and evaluations for bioactivities. Journal of Inorganic Biochemistry 2007; 101: 412-421. doi: 10.1016/j.jinorgbio.2006.11.001
  • 25. Bushuev M., Krivopalov VP, Semikolenova NV, Shvedenkov YG, Sheludyakova LA et al. Cu(II) Complexes with 4,6-Bis(3,5-dimethyl-1Hpyrazole-1-yl)pyrimidine,4-(3,5-dimethyl-1H-pyrazole-1-yl)-6-(3,5-diphenyl-1H-pyrazole-1-yl)pyrimidine: Synthesis and catalytic activity in ethylene polymerization reaction. Russian Journal of Coordination Chemistry 2007; 33: 8, 601-606. doi: 10.1080/00958972.2012.657187
  • 26. Zhang H, Liu CS, Bu XH, Yang M. Synthesis, crystal structure, cytotoxic activity and DNA-binding properties of the copper (II) and zinc (II) complexes with 1-[3-(2-pyridyl)pyrazol-1-ylmethyl]naphthalene. Journal of Inorganic Biochemistry 2005; 99: 1119-1125. doi: 10.1016/j. jinorgbio.2005.02.005
  • 27. Keter FK, Darkwa J. Perspective: the potential of pyrazole-based compounds in medicine. Biometals 2012; 25: 9-21. doi: 10.1007/s10534-011- 9496-4
  • 28. Molander GA, Ryu DW, Sarvari MH, Devulapally R, Seapy DG. Suzuki-Miyaura cross-coupling of potassium trifluoro(N-methylheteroaryl) borates with aryl and heteroaryl halides. Journal of Organic Chemistry 2013; 78: 6648-6656. doi: 10.1021/jo4009589
  • 29. Boswell MG, Yeung FG, Wolf C. Copper-catalyzed C-N bond formation with N-heterocycles and aryl halides. Synlett 2012; 23 (8): 1240- 1244. doi: 10.1055/s-0031-1290827
  • 30. Wang XY, Liu SQ, Zhang CY, Song G, Bai FY et al. Synthesis, structural, and biological evaluation of the arene-linked pyrazolyl methane ligands and their d9/d10 metal complexes. Polyhedron 2012; 47: 151-164. doi: 10.1016/j.poly.2012.08.016
  • 31. Hurtado J, Ibanez A, Rojas R, Valderrama M, Fröhlich R. Organonickel(II) comlexes with anionic tridentate 1,3-bis(azolylmethyl)phenyl ligands. Synthesis, structural chracterization and catalytic behavior. Journal of Brazilian Chemical Society 2011; 22: 1750-1757. doi: 10.1590/S0103-50532011000900018
  • 32. SADABS, Version 6.02; Bruker Inc.: Madison, WI, 1998-2000.
  • 33. SHELXTL, Version 6.10; Bruker Inc.: Madison, WI, 1998-2000.
  • 34. Farrugia LJ. ORTEP-3 for Windows-a version of ORTEP-III with a Graphical User Interface (GUI) J. Appl. Crystallogr 1997; 30: 565. doi: 10.1107/S0021889897003117
  • 35. Jorgensen, JH, Turnidge JD. Susceptibility test methods: dilution and disk diffusion methods, In: Jorgensen JH, Pfaller MA, Carroll KC, Funke G, Landry ML et al. (editors). Manual of Clinical Microbiology. 11th ed. American Society for Microbiology Press, Washington, USA, 2015; 71: 1253-1273. doi: 10.1128/9781555817381.ch71
  • 36. Mahesh B, Satish S. Antimicrobial activity of some important medicinal plant against plant and human pathogens. World Journal of Agricultural Sciences 2008; 4 (5): 839-843.
  • 37. Wayne, P. National committee for clinical laboratory standards. Performance standards for antimicrobial disc susceptibility testing, Wayne, USA, 2002; 12.
  • 38. Wang DJ, Zheng CY, Fan L. Synthesis, characterization, and crystal structures of new 3,5-diaryl-1H-pyrazoles. Journal of Molecular Structure 2009; 938: 311-315. doi: 10.1016/j.molstruc.2009.10.001
  • 39. Nakamato K. Infrared and Raman Spectra of Inorganic and Coordination Compounds, Part B: Applications in Coordination, Organometallic, and Bioinorganic Chemistry. 6th ed. New Jersey, USA: John Wiley & Sons, Inc., 2009. doi: 10.1002/9780470405888
  • 40. Curtis NF, Curtis YM. Some nitrato-amine nickel(II) compounds with monodentate and bidentate nitrate ions. Inorganic Chemistry 1965; 4: 804-809. doi: 10.1021/ic50028a007
  • 41. Potapov AS, Khlebnikov AI. Synthesis of mixed-ligand copper(II) complexes containing bis(pyrazol-1-yl)methane ligands. Polyhedron 2006; 25: 2683-2690. doi: 10.1016/j.poly.2006.03.016
  • 42. Bagihalli GB, Avaji PG, Patil SA, Badami PS. Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II) and Cu(II) complexes with 1,2,4-triazole Schiff bases. European Journal of Medicinal Chemistry 2008; 43: 2639-2649. doi: 10.1016/j.ejmech.2008.02.013
  • 43. Skoog DA, Holler FJ, Nieman TA. Principles of Instrumental Analysis. 5th ed. Florida, USA: Harcourt Brace &Company, 1998.
  • 44. Balcı M. Nükleer Manyetik Rezonans Spektroskopisi, İkinci Basım, ODTÜ Yayıncılık, Ankara, 2004 (in Turkish).
  • 45. Yang G, Raptis RG. Synthesis, characterization and crystal structures of two 2-naphthyl substituted pyrazoles. Journal of Heterocyclic Chemistry 2003; 40: 659-664. doi: 10.1002/jhet.5570400416
  • 46. Sharma S, Barooah N, Baruah JB. Tris (3,5-dimethylpyrazole) copper(II) nitrate: as an oxidation catalyst. Journal of Molecular Catalysis A: Chemical 2005; 229: 171-176. doi: 10.1016/j.molcata.2004.11.019
  • 47. Geary WJ. The Use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord. Chem. Rev 1971; 7: 81-122. doi: 10.1016/S0010-8545(00)80009-0
  • 48. Sunitha S. Synthesis and characterization of biologically important metal complexes. PhD, University of Calicut, Kerala, India, 2008.
  • 49. Wu F, Tong H, Wang K, Zhang X, Zhang J et al. Mononuclear copper(I) bromide complexes chelated with bis(pyrazol-1- ylmethyl)- pyridine ligands: Structures, electronic properties and solid state photoluminescence. Journal of Luminescence 2016; 177: 82-87. doi: 10.1016/j.jlumin.2016.04.021
  • 50. Hathaway BJ, Billing DE. The electronic properties and stereochemistry of mono-nuclear complexes of the copper(II) ion. Coordination Chemistry Reviews 1969; 5: 143-207. doi: 10.1016/S0010-8545(00)80135-6
  • 51. Reddy SL, Endo T, Reddy GS. Electronic (Absorption) Spectra of 3D transition metal complexes, advanced aspects of spectroscopy. IntechOpen 2012; 548. doi: 10.5772/50128
  • 52. Ray RK, Kauffman GB. EPR spectra and covalency of bis(amidinourea/o alkyl-1-amidinourea)copper(II) complexes, Part II. Properties of the CuN4 2- chromophore. Inorganica Chimica Acta 1990; I73: 207-214. doi: 10.1016/S0020-1693(00)80215-7
  • 53. Shanmugakala R, Tharmaraj P, Sheela CD. Synthesis and spectral studies on metal complexes of s-triazine based ligand and non linear optical properties. Journal of Molecular Structure 2014; 1076: 606-613. doi: 10.1016/j.molstruc.2014.08.012
  • 54. Benial AMF, Ramakrishnan V, Murugesan R. Single crystal EPR of $Cu(C_5H_5NO)_6(BF_4)_2$ : an example of admixed ground state. Spectrochimica Acta Part A 2000; 56: 2775-2781. doi: 10.1016/S1386-1425(00)00322-X
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Electrochemical investigation of the interaction of 2,4-D and double stranded DNA using pencil graphite electrodes

Gülşah ÇONGUR

Synthesis and molecular docking study of novel COVID-19 inhibitors

Zuhal GERÇEK, Deniz CEYHAN, Erol ERÇAĞ

Synthesis and characterization of magnetic nanocomposite for in vitro evaluation of irinotecan using human cell lines

Tuba TARHAN

Evaluation of the surface properties of 4-(Decyloxy) benzoic acid liquid crystal and its use in structural isomer separation

Özlem CANKURTARAN, Fatih ÇAKAR, Birol IŞIK, Hüsnü CANKURTARAN

Removal of COD, aromaticity and color of a pretreated chemical producing industrial wastewater: a comparison between adsorption, ozonation, and advanced oxidation processes

Deniz İzlen ÇİFÇİ, Elçin GÜNEŞ, Yalçın GÜNEŞ, Ali Rıza DİNÇER

The synthesis and characterization of polyorganosiloxane nanoparticles from 3-mercaptopropyltrimethoxysilane for preparation of nanocomposite films via photoinitiated thiol-ene polymerization

Nurcan KARACA

The protective role of melatonin under heavy metal-induced stress in Melissa Officinalis L.

Elvisa HODŽIĆ, Milica BALABAN, Biljana KUKAVICA, Dijana MIHAJLOVIĆ, Sebila REKANOVIĆ, Halid MAKIĆ, Semira GALIJAŠEVIĆ

Synthesis, characterization and catalytic properties of cationic N-heterocyclic carbene silver complexes

Deniz DEMİR ATLI

Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities

Rezzan ALİYAZICIOĞLU, Şeyda KANBOLAT, Hasan Erdinç SELLİTEPE, Nuran KAHRİMAN, Şengül ALPAY KARAOĞLU, Arif BOZDEVECİ, İnci Selin DOĞAN, Gonca ÇELİK, Ali AYDIN, Nurettin YAYLI, Gözde KILIÇ

Novel Mannich bases with strong carbonic anhydrases and acetylcholinesterase inhibition effects: 3-(aminomethyl)-6-{3-[4-(trifluoromethyl)phenyl]acryloyl}-2(3H)- benzoxazolones

Yeliz DEMİR, İlhami GÜLÇİN, Barış ANIL, Mehmet KOCA, Sinan BiLGiNER