Acta Scientific Pharmaceutical Sciences (ASPS)(ISSN: 2581-5423)

Research Article Volume 7 Issue 8

Copper(II) Complexes of an N-pendent Cyanoethyl Derivative of a Tetraazamacrocyclic Ligand: Synthesis, Characterization and Antibacterial Studies

Suravi Dhar1, Saswata Rabi2, Pradip Paul1, Avijit Chakraborty1, Benu Kumar Dey1 and Tapashi Ghosh Roy1*

1Department of Chemistry, University of Chittagong, Chattogram, Bangladesh
2Department of Chemistry, Chittagong University of Engineering and Technology, Chattogram, Bangladesh

*Corresponding Author: Tapashi Ghosh Roy, Department of Chemistry, University of Chittagong, Chattogram, Bangladesh.

Received: June 06, 2023; Published: July 14, 2023

Abstract

One of the isomers of the ligand Me6[14]ane, ‘tet-b’ upon reflux with acrylonitrile produced N-pendent derivative ‘tet-bx’ in which two cyano-ethyl groups were attached on less crowded two trans-N atoms. The reaction of copper(II) perchlorate hexahydrate with ‘tet-bx’ yielded six coordinated octahedral reddish-purple [Cu(tet-bx)(ClO4)2]. The axial substitution reactions of [Cu(tet-bx)(ClO4)2] with KX (X= SCN, NO3, Cl, Br or I) and NaNO2 afforded six coordinated blue [Cu(tet-bx)(NCS)(ClO4)] and [Cu(tet-bx)(NO2)(H2O)]ClO4; red [Cu(tet-bx)(NO3)(H2O)]ClO4 and [Cu(tet-bx)Cl(H2O)]ClO4 and purple [Cu(tet-bx)Br(H2O)]ClO4 and [Cu(tet-bx)I(H2O)]ClO4. The complexes were characterized on the basis of elemental, spectroscopic, magnetochemical and conductometric analysis. The antibacterial activities of the concerned ligand and its copper(II) complexes have been tested against four selected bacteria.

 Keywords: N-pendant Tetraazamacrocyclic Ligand; Copper (II) Complexes; Spectroscopic Studies; Antibacterial Activities

References

  1. Haque A., et al. “Coordination chemistry and application of mono- and oligopyridine-based macrocycles”. Coordination Chemistry Reviews 350 (2017): 320-339.
  2. Mewis RE., et al. “Biomedical applications of macrocyclic ligand complexes”. Coordination Chemistry Reviews 15-16 (2010): 1686-1712.
  3. Mallinson J., et al. “Macrocycles in new drug discovery”. Future Medicinal Chemistry 11 (2012): 1409-1438.
  4. Liang F., et al. “Medical Applications of Macrocyclic Polyamines”. Current Medicinal Chemistry 6 (2006): 711-727.
  5. Ermert P. “Design, Properties and Recent Application of Macrocycles in Medicinal Chemistry”. CHIMIA International Journal for Chemistry10 (2017): 678-702.
  6. Kantekin H., et al. “New heavy metal ion-selective macrocyclic ligands with mixed-donor atoms and their extractant properties”. Journal of Coordination Chemistry 63.11 (2010): 1921-1932.
  7. Hu L., et al. “Kinetic determination of Ag+ using a novel Belousov-Zhabotinskii oscillating system catalyzed by a macrocyclic complex”. Journal of Analytical Chemistry 61.10 (2006): 1021-1025.
  8. Ogoshi T., et al. “Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry”. Chemical Reviews 116.14 (2016): 7937-8002.
  9. Bowman-James K. “Macrocyclic Ligands, Encyclopedia of Inorganic Chemistry”. John Wiley and Sons, Ltd (2006).
  10. Reddy PM., et al. “Synthesis, Spectral and Antibacterial Studies of Copper(II) Tetraaza Macrocyclic Complexes”. International Journal of Molecular Sciences4 (2012): 4982-4992.
  11. Raman N. “Antifungal active tetraaza macrocyclic transition metal complexes: Designing, template synthesis, and spectral characterization”. Russian Journal of Coordination Chemistry 35.3 (2009): 234-238.
  12. Pawar V., et al. “Synthesis, antioxidant and biocidal features of macrocyclic Schiff bases with oxovanadium (V) complexes”. Journal of Chemical and Pharmaceutical Research 3.1 (2011): 169-175.
  13. Lücking U., et al. “Macrocyclic Aminopyrimidines as Multitarget CDK and VEGF-R Inhibitors with Potent Antiproliferative Activities”. ChemMedChem1 (2007): 63-77.
  14. Roy M., et al. “Synthesis, characterization and anti-diabetic activities of triorganotin(IV) azo-carboxylates derived from amino benzoic acids and resorcinol: Crystal structure and topological study of a 48 membered macrocyclic-tetrameric trimethyltin(IV) complex”. Inorganica Chimica Acta 439 (2016): 164-172.
  15. Liang F., et al. “Copper complex of hydroxyl-Substituted triazamacrocyclic ligand and its antitumor activity”. Bioorganic and Medicinal Chemistry Letters15 (2003): 2469-2472.
  16. Kareem A., et al. “Synthesis, characterization and in vitro anticancer activity of 18-membered octaazamacrocyclic complexes of Co(II), Ni(II), Cd(II) and Sn(II)”. Journal of Molecular Structure 1075 (2014): 17-25.
  17. Kumar K., et al. “Macrocyclic polyaminocarboxylate complexes of lanthanides as magnetic resonance imaging contrast agents”. Pure and Applied Chemistry 65.3 (1993): 515-520.
  18. Majkowska-Pilip A., et al. “Macrocyclic complexes of scandium radionuclides as precursors for diagnostic and therapeutic radiopharmaceuticals”. Journal of Inorganic Biochemistry 2 (2011): 313-320.
  19. Villagra E. “Tuning the redox properties of Co-N4 macrocyclic complexes for the catalytic electrooxidation of glucose”. Electrochimica Acta 14 (2008): 4883-4888.
  20. Sharma CVK. “Discrete Macrocycles to Infinite Polymeric Frames: Crystal Engineering Studies of Ag(I): Pyrimidine Complexes”. Crystal Engineering 1 (1998): 19-38.
  21. Roy TG., et al. “Synthesis and antimicrobial activities of copper(II) complexes of N(4),N(11)-dimethyl (LBZ & LCZ) and N(4)-monomethyl (LCZ1)-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane. Crystal and molecular structure of [CuLCZ1](ClO4)2”. Inorganica Chimica Acta 415 (2014): 124-131.
  22. Nath BC., et al. “Two solvatomorphic forms of a copper complex formulated as Cu(L)(ClO4)2.2(H2O)(I) and Cu(L)(ClO4)2 (II), where L is 3,10-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11 -tetraazacyclotetradecane, C18H40N4”. Acta Crystallographica C69 (2013): 689-695.
  23. Roy , et al. “[(4E,11E)- 5,7,12,14-Tetrabenzyl-7,14-dimethyl-1,4,8,11-tetraazacyclotetradeca-4,11-diene]copper(II)bis (perchlorate)”. Acta Crystallographica E67 (2011): 1581-1582.
  24. Roy , et al. “Copper(II) and nickel(II) complexes of N,N-bis(2-hydroxyethyl)-octamethyl-1,4,8,11-tetraaza-cyclotetradecane”. European Journal of Inorganic Chemistry (2004): 4115-4123.
  25. Dey L., et al. “Copper(II) and nickel(II) complexes of an N-pendent bis-(cyanoethyl) derivative of an isomeric hexamethyl tetraazamarocyclic ligand: Synthesis, characterization, electrolytic behavior and antimicrobial studies”. Inorganica Chimica Acta 512 (2021): 1-7.
  26. Yasmin S., et al. “Three transition-metal complexes with the macrocyclic ligand meso-5,7,7,12,14,14,-hexamethyl-1,4,8,11-tetraazacyclotetradecane (L): [Cu(ClO4)2(L)], [Zn(NO3)2(L)] and [CuCl(L)(H2O)]Cl”. Acta Crystallographica C69 (2013): 862-867.
  27. Yasmin S. et al. “Synthesis, characterization and antibacterial studies of zinc(II) complexes with hexamethyl-tetraazacyclotetradecadiene Me6[14]diene and C-chiral isomers of its reduced analogue”. Journal of Inclusion Phenomena and Macrocyclic Chemistry 87 (2017): 239-250.
  28. Barua S., et al. “Palladium complexes with hexamethyl tetraazacyclotetradecadiene (L) and isomers of its reduced form (‘tet-a’ & ‘tet-b’): synthesis, characterization and antimicrobial studies”. Journal of Inclusion Phenomena and Macrocyclic Chemistry 86 (2016): 291-303.
  29. Biswas FB., et al. “Synthesis, characterization and electrolytlic behavior of cadmium(II) complexes of 5,7,7,12,14,14-hexamethyl-1,4,8,11 tetraazacyclotetradeca-4,11-diene and isomers of its saturated analogue”. European Scientific Journal 12 (2016): 186-200.
  30. Hay RW., et al. “A convenient synthesis of the tetra-aza-macrocyclic ligands trans-[14]-diene, tet a, and tet b”. Journal of the Chemical Society, Perkins Transactions 1.6 (1975): 591-593.
  31. Roy TG., et al. “Synthesis, characterization and antifungal activities of some new copper(II) complexes of octamethyl tetraazacyclotetradecadiene”. Metal Based Drugs, 6.6 (1999): 345-354.
  32. Farago ME., et al. “Coordination of Thiocyanate and Selenocyanate in Some Diamine Complexes of Nickel(II) and Copper(II)”. Inorganic Chemistry 4.12 (1965): 1706-1711.
  33. Sabatini A., et al. “Infrared Spectra between 100 and 2500 Cm-1 of Some Complex Metal Cyanates, Thiocyanates, and Selenocyanates”. Inorganic Chemistry7 (1965): 959-961.
  34. Roy , et al.Axial addition in diastereoisomeric [Cu(Me8[14]ane)](ClO4)2] complexes: Anti-fungal and anti- bacterial activities”. Journal of Coordination Chemistry 59.15 (2006): 1757-1767.
  35. Geary WJ. “The use of conductivity measurements in organic solvents for the characterisation of coordination compounds”. Coordination Chemistry Reviews 7.1 (1971): 81-122.
  36. Roy TG., et al. “Synthesis, electrolytic behaviour and antimicrobial activities of cadmium complexes of isomers of 3,10-C-meso- 3,5,7,7,10,12,14,14-octamethyl- 1,4,8,11- tetraazacyclotetradecane”. Journal of Coordination Chemistry 40 (2007): 1567-1578.
  37. Roy TG., et al. “Synthesis of some octahedral nickel(II) complexes of one isomer of isomeric Me8[14]anes: X-ray structure of diisothiocyanato(3,10-C-meso-3,5,7,7,10,12,14,14-octamethyl- 1,4,8,11- tetraazacyclotetradecane, LC)nickel(II), [NiLC(NCS)2]”. Journal of Inclusion Phenomena and Macrocyclic Chemistry 58 (2007): 249-255.
  38. Nakamoto K. “Infrared and Raman Spectra of Inorganic and Coordination Compounds (John Willey, New York)” 1963.
  39. Roy TG., et al. “Studies on some transition metal complexes of 3,10-C-meso- 3,5,7,7,10,12,14,14-octamethyl- 1,4,8,11- tetraazacyclotetradeca – 4,11-diene”. Ceylon Journal of Science 11 (2006): 37-49.

Citation

Citation: Tapashi Ghosh Roy., et al. “Copper(II) Complexes of an N-pendent Cyanoethyl Derivative of a Tetraazamacrocyclic Ligand: Synthesis, Characterization and Antibacterial Studies". Acta Scientific Pharmaceutical Sciences 7.8 (2023): 33-41.

Copyright

Copyright: © 2023 Tapashi Ghosh Roy., et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.




Metrics

Acceptance rate32%
Acceptance to publication20-30 days

Indexed In




News and Events


Contact US