Research Article
BibTex RIS Cite

Synthesis, Spectroscopic Analysis, and Anti-Bacterial Studies of Pd(II) Complexes of Phosphine and Hydrazone Derivatives

Year 2024, , 245 - 252, 04.02.2024
https://doi.org/10.18596/jotcsa.1343254

Abstract

This study reports the synthesis of seven hydrazone derivative complexes by the treatment equivalent molar of the phosphine ligand Ph2P(CH2)nPPh2 {where n= 1 dppm; n=2 dppe; n=3 dppp; n=4
dppb; (CH2)n = (Cp)2Fe} with [Pd(dbeoz)2] afforded complexes of the type [Pd(dbeoz)2(diphos)] and [Pd(dbeoz)2(dppm)]2, whereas the reaction of two moles of Ph3P with [Pd(dbeoz)2] gave a complex [Pd(dbeoz)2(PPh3)2] in good yield. CHN analysis, conductivity measurements, Fourier Transform Infrared (FT-IR), 1H, and 31P-NMR, were used to investigate the structural geometries of the complexes. Further, the biological activity of the synthesized complexes was evaluated against three pathogenic bacteria (Pseudomonas aeruginosa, Bacillus subtilis, and Escherichia coli) using the well diffusion method, the synthesized complexes displayed moderate to good inhibitory activity, and the [Pd(dbeoz)2(dppf)] complex exhibited the highest inhibitory activity with DIZ is 24, 27, and 28 mm against the three pathogenic bacteria, respectively.

Thanks

The authors are thankful to Tikrit University for supporting this work

References

  • 1. Shakdofa MME, Shtaiwi MH, Morsy N, Abdel-rassel TMA. Metal complexes of hydrazones and their biological, analytical and catalytic applications: A review. Main Group Chemistry. 2014;13(3):187–218. Available from: <URL>.
  • 2. Kumar M, Roy S, Faizi MdSH, Kumar S, Singh MK, Kishor S, et al. Synthesis, crystal structure and luminescence properties of acenaphthene benzohydrazide based ligand and its zinc(II) complex. Journal of Molecular Structure. 2017 Jan;1128:195–204. Available from: <URL>.
  • 3. Tabernero V, Cuenca T, Herdtweck E. Hydrazonide titanium derivatives. Journal of Organometallic Chemistry. 2002 Dec;663(1–2):173–82. Available from: <URL>.
  • 4. Pelagatti P, Carcelli M, Pelizzi C, Costa M. Polymerisation of phenylacetylene in water catalysed by Pd(NN′O)Cl complexes. Inorganica Chimica Acta. 2003 Jan;342:323–6. Available from: <URL>.
  • 5. Chen L. Ethylene oligomerization by hydrazone Ni(II) complexes/MAO. Applied Catalysis A: General. 2003 Jun 25;246(1):11–6. Available from: <URL>.
  • 6. Zhong X, Wei HL, Liu WS, Wang DQ, Wang X. The crystal structures of copper(II), manganese(II), and nickel(II) complexes of a (Z)-2-hydroxy-N′-(2-oxoindolin-3-ylidene) benzohydrazide—potential antitumor agents. Bioorganic & Medicinal Chemistry Letters. 2007 Jul;17(13):3774–7. Available from: <URL>.
  • 7. Cullen STJ, Friestad GK. Alkyl Radical Addition to Aliphatic and Aromatic N -Acylhydrazones Using an Organic Photoredox Catalyst. Organic Letters. 2019 Oct 18;21(20):8290–4. Available from: <URL>.
  • 8. Kvasovs N, Gevorgyan V. Accessing Illusive E Isomers of α-Ester Hydrazones via Visible-Light-Induced Pd-Catalyzed Heck-Type Alkylation. Organic Letters. 2022 Jun 17;24(23):4176–81. Available from: <URL>.
  • 9. Prieto A, Bouyssi D, Monteiro N. Radical‐Mediated Formal C(sp 2 )–H Functionalization of Aldehyde‐Derived N , N ‐Dialkylhydrazones. European Journal of Organic Chemistry. 2018 Jun 7;2018(20–21):2378–93. Available from: <URL>.
  • 10. Xu X, Zhang J, Xia H, Wu J. C(sp 2 )–H functionalization of aldehyde-derived hydrazones via a radical process. Organic and Biomolecular Chemistry. 2018;16(8):1227–41. Available from: <URL>.
  • 11. El-Tabl AS, Mohamed Abd El-Waheed M, Wahba MA, Abd El-Halim Abou El-Fadl N. Synthesis, Characterization, and Anticancer Activity of New Metal Complexes Derived from 2-Hydroxy-3-(hydroxyimino)-4-oxopentan-2-ylidene)benzohydrazide. Bioinorganic Chemistry and Applications. 2015;2015:1–14. Available from: <URL>.
  • 12. Okagu OD, Ugwu KC, Ibeji CU, Ekennia AC, Okpareke OC, Ezeorah CJ, et al. Synthesis and characterization of Cu(II), Co(II) and Ni(II) complexes of a benzohydrazone derivative: Spectroscopic, DFT, antipathogenic and DNA binding studies. Journal of Molecular Structure. 2019 May;1183:107–17. Available from: <URL>.
  • 13. Katouah HA, Al-Fahemi JH, Elghalban MG, Saad FA, Althagafi IA, El-Metwaly NM, et al. Synthesis of new Cu(II)-benzohydrazide nanometer complexes, spectral, modeling, CT-DNA binding with potential anti-inflammatory and anti-allergic theoretical features. Materials Science and Engineering: C. 2019 Mar;96:740–56. Available from: <URL>.
  • 14. Al-Qadsy I, Al-Odayni AB, Saeed WS, Alrabie A, Al-Adhreai A, Al-Faqeeh LAS, et al. Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene) benzohydrazide–Nickel(II)] Complex. Crystals. 2021 Jan 26;11(2):110. Available from: <URL>.
  • 15. Korkmaz IN, Türkeş C, Demir Y, Öztekin A, Özdemir H, Beydemir Ş. Biological evaluation and in silico study of benzohydrazide derivatives as paraoxonase 1 inhibitors. J Biochemistry & Molecular Toxicity. 2022 Nov;36(11):e23180. Available from: <URL>.
  • 16. Zuo W, Tourbillon C, Rosa V, Cheaib K, Andrade MM, Dagorne S, et al. Synthesis, crystal structures and use in ethylene oligomerization catalysis of novel mono- and dinuclear nickel complexes supported by (E)-N′-(1-(thiophen-2-yl)ethylidene)benzohydrazide ligand. Inorganica Chimica Acta. 2012 Mar;383:213–9. Available from: <URL>.
  • 17. Burgos-Lopez Y, Del Plá J, Balsa LM, León IE, Echeverría GA, Piro OE, et al. Synthesis, crystal structure and cytotoxicity assays of a copper(II) nitrate complex with a tridentate ONO acylhydrazone ligand. Spectroscopic and theoretical studies of the complex and its ligand. Inorganica Chimica Acta. 2019 Mar;487:31–40. Available from: <URL>.
  • 18. Theppitak C, Kielar F, Dungkaew W, Sukwattanasinitt M, Kangkaew L, Sahasithiwat S, et al. The coordination chemistry of benzhydrazide with lanthanide( iii ) ions: hydrothermal in situ ligand formation, structures, magnetic and photoluminescence sensing properties. RSC Advances. 2021;11(40):24709–21. Available from: <URL>.
  • 19. Guan Q, Zhou LL, Dong YB. Metalated covalent organic frameworks: from synthetic strategies to diverse applications. Chemical Society Reviews. 2022; 51(15):6307–416. Available from: <URL>.
  • 20. Zhao J, Yuan J, Fang Z, Huang S, Chen Z, Qiu F, et al. One-dimensional coordination polymers based on metal–nitrogen linkages. Coordination Chemistry Reviews. 2022 Nov;471:214735. Available from: <URL>.
  • 21. Sánchez-Fernández JA. Structural Strategies of Supramolecular Hydrogels and Their Applications [Internet]. Chemistry; 2023 Feb [cited 2023 Dec 1]. Available from: <URL>.
  • 22. Bauer AW. Single-Disk Antibiotic-Sensitivity Testing of Staphylococci: An Analysis of Technique and Results. JAMA Internal Medicine. 1959 Aug 1;104(2):208. Available from: <URL>.
  • 23. Mohamed DS, Al-Jibori SA, Behjatmanesh-Ardakani R, Faihan AS, Yousef TA, Alhamzani AG, et al. Spectroscopic, Anti-Cancer Activity, and DFT Computational Studies of Pt(II) Complexes with 1-Benzyl-3-phenylthiourea and Phosphine/Diamine Ligands. Inorganics. 2023 Mar 16;11(3):125. Available from: <URL>.
  • 24. Al-Janabi ASM, Yousef TA, Al-Doori MEA, Bedier RA, Ahmed BM. Palladium(II)-salicylanilide complexes as antibacterial agents: Synthesis, spectroscopic, structural characterization, DFT calculations, biological and in silico studies. Journal of Molecular Structure. 2021 Dec;1246:131035. Available from:<URL>.
  • 25. Al-Jibori SA, Al-Jibori GHH, Saleh SS, Al-Janabi AS, Laguna M, Wagner C. Mercury (II) benzisothiazolinate (bit) complexes with diamine or phosphine co-ligands, and subsequent conversion to 2-mercaptobenzamide complexes. Crystal structures of [Hg(bit)2(L2)], L2 = bipyridine or phenanthroline. Polyhedron. 2021 Sep;206:115353. Available from: <URL>.
  • 26. Salih MM, Saleh AM, Hamad AS, Al-Janabi AS. Synthesis, spectroscopic, anti-bacterial activity, molecular docking, ADMET, toxicity and DNA binding studies of divalent metal complexes of pyrazole-3-one azo ligand. Journal of Molecular Structure. 2022 Sep;1264:133252. Available from: <URL>.
  • 27. Al-Janabi ASM, Oudah KH, Aldossari SA, Khalaf MA, M. Saleh A, Hatshan MR, et al. Spectroscopic, anti-bacterial, anti-cancer and molecular docking of Pd(II) and Pt(II) complexes with (E)-4-((dimethylamino)methyl)-2-((4,5-dimethylthiazol-2-yl)diazenyl)phenol ligand. Journal of Saudi Chemical Society. 2023 May;27(3):101619. Available from: <URL>.
  • 28. Afandi ZS, Al-Jibori SA, Ferjani H, Al-Shammar RH, Aldossari SA, Al-Janabi AS. Ortho-palladated complexes with aromatic N-donor ligands, synthesis, characterization, molecular structures, antibacterial and anticancer activity [Internet]. In Review; 2022 Oct [cited 2023 Dec 1]. Available from: <URL>.
  • 29. Al-Janabi ASM, Elzupir AO, Abou-Krisha MM, Yousef TA. New Dual Inhibitors of SARS-CoV-2 Based on Metal Complexes with Schiff-Base 4-Chloro-3-Methyl Phenyl Hydrazine: Synthesis, DFT, Antibacterial Properties and Molecular Docking Studies. Inorganics. 2023 Jan 29;11(2):63. Available from: <URL>.
  • 30. Al-Janabi AMA, Faihan AS, Al-Mutairi AM, Hatshan MR, Al-Jibori SA, Al-Janabi ASM. Spectroscopic, biological activity studies, and DFT calculations, of Pd(II) and Pt(II) complexes of 4-Methylene-3-phenyl-3,4-dihydroquinazoline-2(1H)-thione. Journal of the Indian Chemical Society. 2022 Nov;99(11):100774. Available from: <URL>.
  • 31. Al-Jibori LH, Al-Janabi AS. Spectroscopic characterization, and anti-bacterial activity studies of the benzohydrazide derivatives complexes. Microbial Science Archives. 2023;3(3):141–6.
Year 2024, , 245 - 252, 04.02.2024
https://doi.org/10.18596/jotcsa.1343254

Abstract

References

  • 1. Shakdofa MME, Shtaiwi MH, Morsy N, Abdel-rassel TMA. Metal complexes of hydrazones and their biological, analytical and catalytic applications: A review. Main Group Chemistry. 2014;13(3):187–218. Available from: <URL>.
  • 2. Kumar M, Roy S, Faizi MdSH, Kumar S, Singh MK, Kishor S, et al. Synthesis, crystal structure and luminescence properties of acenaphthene benzohydrazide based ligand and its zinc(II) complex. Journal of Molecular Structure. 2017 Jan;1128:195–204. Available from: <URL>.
  • 3. Tabernero V, Cuenca T, Herdtweck E. Hydrazonide titanium derivatives. Journal of Organometallic Chemistry. 2002 Dec;663(1–2):173–82. Available from: <URL>.
  • 4. Pelagatti P, Carcelli M, Pelizzi C, Costa M. Polymerisation of phenylacetylene in water catalysed by Pd(NN′O)Cl complexes. Inorganica Chimica Acta. 2003 Jan;342:323–6. Available from: <URL>.
  • 5. Chen L. Ethylene oligomerization by hydrazone Ni(II) complexes/MAO. Applied Catalysis A: General. 2003 Jun 25;246(1):11–6. Available from: <URL>.
  • 6. Zhong X, Wei HL, Liu WS, Wang DQ, Wang X. The crystal structures of copper(II), manganese(II), and nickel(II) complexes of a (Z)-2-hydroxy-N′-(2-oxoindolin-3-ylidene) benzohydrazide—potential antitumor agents. Bioorganic & Medicinal Chemistry Letters. 2007 Jul;17(13):3774–7. Available from: <URL>.
  • 7. Cullen STJ, Friestad GK. Alkyl Radical Addition to Aliphatic and Aromatic N -Acylhydrazones Using an Organic Photoredox Catalyst. Organic Letters. 2019 Oct 18;21(20):8290–4. Available from: <URL>.
  • 8. Kvasovs N, Gevorgyan V. Accessing Illusive E Isomers of α-Ester Hydrazones via Visible-Light-Induced Pd-Catalyzed Heck-Type Alkylation. Organic Letters. 2022 Jun 17;24(23):4176–81. Available from: <URL>.
  • 9. Prieto A, Bouyssi D, Monteiro N. Radical‐Mediated Formal C(sp 2 )–H Functionalization of Aldehyde‐Derived N , N ‐Dialkylhydrazones. European Journal of Organic Chemistry. 2018 Jun 7;2018(20–21):2378–93. Available from: <URL>.
  • 10. Xu X, Zhang J, Xia H, Wu J. C(sp 2 )–H functionalization of aldehyde-derived hydrazones via a radical process. Organic and Biomolecular Chemistry. 2018;16(8):1227–41. Available from: <URL>.
  • 11. El-Tabl AS, Mohamed Abd El-Waheed M, Wahba MA, Abd El-Halim Abou El-Fadl N. Synthesis, Characterization, and Anticancer Activity of New Metal Complexes Derived from 2-Hydroxy-3-(hydroxyimino)-4-oxopentan-2-ylidene)benzohydrazide. Bioinorganic Chemistry and Applications. 2015;2015:1–14. Available from: <URL>.
  • 12. Okagu OD, Ugwu KC, Ibeji CU, Ekennia AC, Okpareke OC, Ezeorah CJ, et al. Synthesis and characterization of Cu(II), Co(II) and Ni(II) complexes of a benzohydrazone derivative: Spectroscopic, DFT, antipathogenic and DNA binding studies. Journal of Molecular Structure. 2019 May;1183:107–17. Available from: <URL>.
  • 13. Katouah HA, Al-Fahemi JH, Elghalban MG, Saad FA, Althagafi IA, El-Metwaly NM, et al. Synthesis of new Cu(II)-benzohydrazide nanometer complexes, spectral, modeling, CT-DNA binding with potential anti-inflammatory and anti-allergic theoretical features. Materials Science and Engineering: C. 2019 Mar;96:740–56. Available from: <URL>.
  • 14. Al-Qadsy I, Al-Odayni AB, Saeed WS, Alrabie A, Al-Adhreai A, Al-Faqeeh LAS, et al. Synthesis, Characterization, Single-Crystal X-ray Structure and Biological Activities of [(Z)-N′-(4-Methoxybenzylidene) benzohydrazide–Nickel(II)] Complex. Crystals. 2021 Jan 26;11(2):110. Available from: <URL>.
  • 15. Korkmaz IN, Türkeş C, Demir Y, Öztekin A, Özdemir H, Beydemir Ş. Biological evaluation and in silico study of benzohydrazide derivatives as paraoxonase 1 inhibitors. J Biochemistry & Molecular Toxicity. 2022 Nov;36(11):e23180. Available from: <URL>.
  • 16. Zuo W, Tourbillon C, Rosa V, Cheaib K, Andrade MM, Dagorne S, et al. Synthesis, crystal structures and use in ethylene oligomerization catalysis of novel mono- and dinuclear nickel complexes supported by (E)-N′-(1-(thiophen-2-yl)ethylidene)benzohydrazide ligand. Inorganica Chimica Acta. 2012 Mar;383:213–9. Available from: <URL>.
  • 17. Burgos-Lopez Y, Del Plá J, Balsa LM, León IE, Echeverría GA, Piro OE, et al. Synthesis, crystal structure and cytotoxicity assays of a copper(II) nitrate complex with a tridentate ONO acylhydrazone ligand. Spectroscopic and theoretical studies of the complex and its ligand. Inorganica Chimica Acta. 2019 Mar;487:31–40. Available from: <URL>.
  • 18. Theppitak C, Kielar F, Dungkaew W, Sukwattanasinitt M, Kangkaew L, Sahasithiwat S, et al. The coordination chemistry of benzhydrazide with lanthanide( iii ) ions: hydrothermal in situ ligand formation, structures, magnetic and photoluminescence sensing properties. RSC Advances. 2021;11(40):24709–21. Available from: <URL>.
  • 19. Guan Q, Zhou LL, Dong YB. Metalated covalent organic frameworks: from synthetic strategies to diverse applications. Chemical Society Reviews. 2022; 51(15):6307–416. Available from: <URL>.
  • 20. Zhao J, Yuan J, Fang Z, Huang S, Chen Z, Qiu F, et al. One-dimensional coordination polymers based on metal–nitrogen linkages. Coordination Chemistry Reviews. 2022 Nov;471:214735. Available from: <URL>.
  • 21. Sánchez-Fernández JA. Structural Strategies of Supramolecular Hydrogels and Their Applications [Internet]. Chemistry; 2023 Feb [cited 2023 Dec 1]. Available from: <URL>.
  • 22. Bauer AW. Single-Disk Antibiotic-Sensitivity Testing of Staphylococci: An Analysis of Technique and Results. JAMA Internal Medicine. 1959 Aug 1;104(2):208. Available from: <URL>.
  • 23. Mohamed DS, Al-Jibori SA, Behjatmanesh-Ardakani R, Faihan AS, Yousef TA, Alhamzani AG, et al. Spectroscopic, Anti-Cancer Activity, and DFT Computational Studies of Pt(II) Complexes with 1-Benzyl-3-phenylthiourea and Phosphine/Diamine Ligands. Inorganics. 2023 Mar 16;11(3):125. Available from: <URL>.
  • 24. Al-Janabi ASM, Yousef TA, Al-Doori MEA, Bedier RA, Ahmed BM. Palladium(II)-salicylanilide complexes as antibacterial agents: Synthesis, spectroscopic, structural characterization, DFT calculations, biological and in silico studies. Journal of Molecular Structure. 2021 Dec;1246:131035. Available from:<URL>.
  • 25. Al-Jibori SA, Al-Jibori GHH, Saleh SS, Al-Janabi AS, Laguna M, Wagner C. Mercury (II) benzisothiazolinate (bit) complexes with diamine or phosphine co-ligands, and subsequent conversion to 2-mercaptobenzamide complexes. Crystal structures of [Hg(bit)2(L2)], L2 = bipyridine or phenanthroline. Polyhedron. 2021 Sep;206:115353. Available from: <URL>.
  • 26. Salih MM, Saleh AM, Hamad AS, Al-Janabi AS. Synthesis, spectroscopic, anti-bacterial activity, molecular docking, ADMET, toxicity and DNA binding studies of divalent metal complexes of pyrazole-3-one azo ligand. Journal of Molecular Structure. 2022 Sep;1264:133252. Available from: <URL>.
  • 27. Al-Janabi ASM, Oudah KH, Aldossari SA, Khalaf MA, M. Saleh A, Hatshan MR, et al. Spectroscopic, anti-bacterial, anti-cancer and molecular docking of Pd(II) and Pt(II) complexes with (E)-4-((dimethylamino)methyl)-2-((4,5-dimethylthiazol-2-yl)diazenyl)phenol ligand. Journal of Saudi Chemical Society. 2023 May;27(3):101619. Available from: <URL>.
  • 28. Afandi ZS, Al-Jibori SA, Ferjani H, Al-Shammar RH, Aldossari SA, Al-Janabi AS. Ortho-palladated complexes with aromatic N-donor ligands, synthesis, characterization, molecular structures, antibacterial and anticancer activity [Internet]. In Review; 2022 Oct [cited 2023 Dec 1]. Available from: <URL>.
  • 29. Al-Janabi ASM, Elzupir AO, Abou-Krisha MM, Yousef TA. New Dual Inhibitors of SARS-CoV-2 Based on Metal Complexes with Schiff-Base 4-Chloro-3-Methyl Phenyl Hydrazine: Synthesis, DFT, Antibacterial Properties and Molecular Docking Studies. Inorganics. 2023 Jan 29;11(2):63. Available from: <URL>.
  • 30. Al-Janabi AMA, Faihan AS, Al-Mutairi AM, Hatshan MR, Al-Jibori SA, Al-Janabi ASM. Spectroscopic, biological activity studies, and DFT calculations, of Pd(II) and Pt(II) complexes of 4-Methylene-3-phenyl-3,4-dihydroquinazoline-2(1H)-thione. Journal of the Indian Chemical Society. 2022 Nov;99(11):100774. Available from: <URL>.
  • 31. Al-Jibori LH, Al-Janabi AS. Spectroscopic characterization, and anti-bacterial activity studies of the benzohydrazide derivatives complexes. Microbial Science Archives. 2023;3(3):141–6.
There are 31 citations in total.

Details

Primary Language English
Subjects Transition Metal Chemistry
Journal Section RESEARCH ARTICLES
Authors

Laith H. K. Al-jibori This is me 0000-0001-8105-7305

Ahmed Shaker Marmus 0000-0003-2722-7419

Publication Date February 4, 2024
Submission Date August 15, 2023
Acceptance Date November 27, 2023
Published in Issue Year 2024

Cite

Vancouver H. K. Al-jibori L, Shaker Marmus A. Synthesis, Spectroscopic Analysis, and Anti-Bacterial Studies of Pd(II) Complexes of Phosphine and Hydrazone Derivatives. JOTCSA. 2024;11(1):245-52.