Snehashis Roy¹, Saswata Rabi², Avijit Chakrabarty¹, Pradip Paul¹, Debashis Palit¹ 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: October 04, 2023; Published: November 03, 2023

Abstract

Isomeric ligand, tet-b was produced by the reduction of hexamethyl tetraazacyclotetradecadiene diperchlorate salt, Me₆[14]diene.2HClO₄ and N–pendent bis-cyanoethyl derivative tet-bx, of this isomeric ligand was obtained by refluxing tet-b with excess of acrylonitrile. Reactions of tet-b and tet-bx with zinc(II) perchlorate and zinc(II) chloride yielded octahedral diperchloratozinc(II) complex, [Zn(tet-b)(ClO₄)₂] and square pyramidal monochloridozinc(II) chloride complex, [Zn(tet-bx)Cl]Cl respectively. The complex, [Zn(tet-b)(ClO₄)] underwent partial axial substitution reactions with KNO₃ and NaNO₂ to yield square pyramidal complexes, mononitratozinc(II) perchlorate, [Zn(tet-b)(NO₃)](ClO₄) and mononitrozinc(II) perchlorate, [Zn(tet-b)(NO₂)](ClO₄) respectively. Moreover, the [Zn(tet-bx)Cl]Cl produced square pyramidal monoisothiocyanatozinc(II) thiocyanate [Zn(tet-bx)(NCS)](NCS) and octahedral diisothiocyanatozinc(II) [Zn(tet-bx)(NCS)₂] complex by undergoing simultaneous axial substitution and anion exchange and axial addition and substitution with KSCN respectively. However, the same complex underwent axial substitution and anion exchange reactions with KNO₃, NaNO_2, KI and KBr to yield square pyramidal complexes, [Zn(tet-bx)(NO₃)](NO₃), [Zn(tet-bx)(NO₂)](NO₂), [Zn(tet-bx)I]I and [Zn(tet-bx)Br]Br respectively. The complexes have been characterized on the basis of analytical and spectroscopic data. The antibacterial activities of the ligands and theirmm new zinc(II) complexes have been investigated against some selected bacteria.

Keywords: N-pendent derivative; Zinc(II) complexes; Characterization; Addition and substitution reactions; Antibacterial

References

1. Shankarwar SG., et al. “Synthesis, spectral, thermal and antimicrobial studies of transition metal complexes of 14-membered tetraaza[N4] macrocyclic ligand”. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 145 (2015): 188-193.
2. Semenov VE., et al. “Antibacterial and antifungal activity of acyclic and macrocyclic uracil derivatives with quaternized nitrogen atoms in spacers”. European Journal of Medicinal Chemistry9 (2006): 1093–1101.
3. Abo-Ghalia MH., et al. “Anticancer activities of newly synthesized chiral macrocyclic heptapeptide candidates”. Molecules1253 (2020): 1-13.
4. Yan L., et al. “An Insight into the Medicinal Chemistry Perspective of Macrocyclic Derivatives with Antitumor Activity: A Systematic Review”. Molecules9 (2022): 2837-2845.
5. Singh RV., et al. “Biologically relevant tetraazamacrocyclic complexes of manganese: synthetic, spectral, antimicrobial, antifertility and antiinflammatory approach”. Journal Inorganic Biochemistry11 (2004): 1712-1721.
6. Pawar V., et al. “Synthesis, antioxidant and biocidal features of macrocyclic schiff bases with oxovanadium (V) complexes”. Journal of Chemical and Pharmaceutical Research1 (2011): 169-175.
7. Jhaumeer-Laulloo BS., et al. “Synthesis and anti-HIV activity of novel macrocyclic disulphide compounds with thioureylene group”. Asian Journal of Chemistry3 (2000): 775-780.
8. Whitty A., et al. “Quantifying the chameleonic properties of macrocycles and other high-molecular-weight drugs”. Drug Discovery Today5 (2016): 712-717.
9. Debanath E., et al. “Vanadium (IV) and vanadium (V) complexes with hexamethyl tetraazamacrocyclic ligands: Synthesis, characterization and antimicrobial studies”. Inorganic Nano-Metal Chemistry9 (2022): 1265-1272.
10. 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 Inclusion Phenomena Macrocycl Chemistry 86 (2016): 291-303.
11. 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 Inclusion Phenomena Macrocyclic Chemistry 87 (2017): 239-250.
12. Rabi S., et al. “Tetraazamacrocyclic Ligands and their Zinc (II) Complexes: Synthesis, Characterization and Biological Activities’’. Acta Scientific Pharmaceutical Sciences8 (2020): 42-54.
13. 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 Journal12 (2016): 186-200.
14. Dhar S., et al. "Copper (II) Complexes of an N-pendent Cyanoethyl Derivative of a Tetraazamacrocyclic Ligand: Synthesis, Characterization and Antibacterial Studies”. Acta Scientific Pharmaceutical Sciences8 (2023): 33-41.
15. 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 Acta120172 (2021) 1-7.
16. Sayed MA., et al. “Studies on cobalt (III) complexes of a cyanoethyl derivative of an isomeric hexamethyl tetraazamacrocyclic ligand”. Journal Inclusion Phenomena Macrocyclic Chemistry 102 (2022): 251-259.
17. Hay RW., et al. “A convenient synthesis of the tetra-aza-macrocyclic ligands trans-[14]-diene, tet a, and tet b”. Journal of Chemical Society Parkins Transaction6 (1975): 591-593.
18. Geary WJ. “The use of conductivity measurements in organic solvents for the characterization of coordination compounds”. Coordination Chemistry Reviews1 (1971): 81-122.
19. Fujita J., et al. “Infrared spectra of metallic complexes. II. The absorption bands of coordinated water in aquo complexes”. American Chemical Society16 (1956): 3963-3965.
20. 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.
21. 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.
22. Nakamoto K. “Infrared and Raman Spectra of Inorganic and Coordination Compounds (John Willey, New York)”. (1963).
23. Salehi M., et al “Characterization, crystal structures, electrochemical and antibacterial studies of four new binuclear cobalt (III) complexes derived from o-aminobenzyl alcohol”. Inorganica Chimica Acta 426 (2015): 6-14.
24. Dharmaraj N., et al. “Ruthenium (II) complexes containing bidentate Schiff bases and their antifungal activity”. Transition Metal Chemistry 26 (2001): 105-109.

Citation

Citation: Tapashi Ghosh Roy., et al. “Zinc(II) Complexes with One Isomer of Tetraazamacrocyclic Ligand and its N-Pendent Bis-cyanoethyl Derivative: Synthesis, Characterization and Antibacterial Studies".Acta Scientific Pharmaceutical Sciences 7.12 (2023): 13-20.

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.