Synthesis, characterization and biological properties of novel ON donor bidentate Schiff bases and their copper(II) complexes

Muhammad Shabbir, Zareen Akhter, Paul R. Raithby, Lynne H. Thomas, Hammad Ismail, Faiza Arshad, Bushra Mirza, Simon J Teat, Khalid Mahmood

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Abstract

Four novel ON donor Schiff bases (E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol (HL1),(E)-3-((4-(4-biphenyloxy)phenyliminomethyl)benzene-1,2-diol (HL2), (E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol (HL3), (E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol (HL4) and their copper(II) complexes bis((E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L1)2) bis((E)-3-((4-(4-biphenyloxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L2)2), bis((E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L3)2), bis((E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L4)2) have been synthesized and characterized by spectroscopic (FTIR, NMR, UV–visible) and elemental analysis. The crystal structures of HL1, HL2, HL3 , and HL4 have been determined, which reveal intramolecular N-H⋯O (HL1, HL2, HL3 , and HL4) hydrogen bonds in the solid state. Keto-amine and enol-imine tautomerism is exhibited by the Schiff bases in solid and solution states. The Schiff bases and their copper(II) complexes have been screened for their biological activities. In antimicrobial assays (antibacterial and antifungal), HL4 showed promising results against all strains through dual inhibition property while the rest of the compounds showed activity against selective strains. On the other hand, in cytotoxic, DPPH, and inhibition of hydroxyl (OH) free radical-induced DNA damage assays, the results were found significantly correlated with each other, i.e. the ligands HL1 and HL2 showed moderate activity while their complexes Cu(L1)2 and Cu(L2)2 exhibited prominent increase in activity. As the results of these assays are supporting each other, it represents the strong positive correlation and antioxidant nature of investigated compounds.

Original languageEnglish
Pages (from-to)2463-2478
Number of pages16
JournalJournal of Coordination Chemistry
Volume70
Issue number14
DOIs
Publication statusPublished - 18 Jul 2017

Fingerprint

Schiff Bases
Toluene
imines
Copper
Benzene
benzene
copper
synthesis
Assays
Imines
solid state
Bioactivity
antioxidants
hydroxyl radicals
Hydroxyl Radical
Free Radicals
Amines
activity (biology)
Antioxidants
Free radicals

Keywords

  • bioactivities
  • copper(II) complexes
  • Schiff bases

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

Synthesis, characterization and biological properties of novel ON donor bidentate Schiff bases and their copper(II) complexes. / Shabbir, Muhammad; Akhter, Zareen; Raithby, Paul R.; Thomas, Lynne H.; Ismail, Hammad; Arshad, Faiza; Mirza, Bushra; Teat, Simon J; Mahmood, Khalid.

In: Journal of Coordination Chemistry, Vol. 70, No. 14, 18.07.2017, p. 2463-2478.

Research output: Contribution to journalArticle

Shabbir, Muhammad ; Akhter, Zareen ; Raithby, Paul R. ; Thomas, Lynne H. ; Ismail, Hammad ; Arshad, Faiza ; Mirza, Bushra ; Teat, Simon J ; Mahmood, Khalid. / Synthesis, characterization and biological properties of novel ON donor bidentate Schiff bases and their copper(II) complexes. In: Journal of Coordination Chemistry. 2017 ; Vol. 70, No. 14. pp. 2463-2478.
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abstract = "Four novel ON donor Schiff bases (E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol (HL1),(E)-3-((4-(4-biphenyloxy)phenyliminomethyl)benzene-1,2-diol (HL2), (E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol (HL3), (E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol (HL4) and their copper(II) complexes bis((E)-3-((4-phenoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L1)2) bis((E)-3-((4-(4-biphenyloxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L2)2), bis((E)-3-((4-naphthoxyphenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L3)2), bis((E)-3-((4-(2-naphthoxy)phenylimino)methyl)benzene-1,2-diol) copper(II) (Cu(L4)2) have been synthesized and characterized by spectroscopic (FTIR, NMR, UV–visible) and elemental analysis. The crystal structures of HL1, HL2, HL3 , and HL4 have been determined, which reveal intramolecular N-H⋯O (HL1, HL2, HL3 , and HL4) hydrogen bonds in the solid state. Keto-amine and enol-imine tautomerism is exhibited by the Schiff bases in solid and solution states. The Schiff bases and their copper(II) complexes have been screened for their biological activities. In antimicrobial assays (antibacterial and antifungal), HL4 showed promising results against all strains through dual inhibition property while the rest of the compounds showed activity against selective strains. On the other hand, in cytotoxic, DPPH, and inhibition of hydroxyl (OH) free radical-induced DNA damage assays, the results were found significantly correlated with each other, i.e. the ligands HL1 and HL2 showed moderate activity while their complexes Cu(L1)2 and Cu(L2)2 exhibited prominent increase in activity. As the results of these assays are supporting each other, it represents the strong positive correlation and antioxidant nature of investigated compounds.",
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AU - Ismail, Hammad

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