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Synthesis, Characterization, Theoretical Studies, and Antimicrobial/Antitumor Potencies of Salen and Salen/Imidazole Complexes of Co (II), Ni (II), Cu (II), Cd (II), Al (III) and La (III)
Author(s) -
Abdalla Ehab M.,
Abdel Rahman Laila H.,
Abdelhamid Antar A.,
Shehata Mohamed R.,
Alothman Asma A.,
Nafady Ayman
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5912
Subject(s) - chemistry , imidazole , reactivity (psychology) , tautomer , ligand (biochemistry) , monobasic acid , stereochemistry , medicinal chemistry , antimicrobial , crystallography , polymer chemistry , organic chemistry , receptor , biochemistry , medicine , alternative medicine , pathology
Although salens and imidazoles are well‐studied motifs among bioactive and therapeutic agents, their properties when combined in transition metal complexes are not well developed. To explore the structure/reactivity of this class of compounds, a salen‐based ligand, namely (2,2′‐{1,2‐ethanediylbis[nitrilo(E)methylylidene]}diphenol, S), and its binary (MS) and ternary (MSI) complexes (I = imidazole; M = Co (II), Ni (II), Cu (II), Cd (II), Al (III), and La (III)) have been synthesized and fully characterized by standard physicochemical and theoretical methods. Evidence from structural analysis tools along with DFT modeling revealed an unusual monobasic tridentate salen binding mode, involving the phenolic oxygen, the nitrogen of the azomethine group, and NH group formed via phenol‐to‐cyclohexadienone tautomerization, giving rise to a general molecular formula of MSI complexes as [M(S)(I) 2 (Cl)] for M (II) = Co, Ni, Cu and Cd or [M(S)(I)(Cl) 2 ] for M (III) = Al and La, respectively. The antimicrobial activities of S, MS, and MSI were screened against several bacterial and fungal strains. Of all tested complexes, CdS and CuSI were the most effective antimicrobials, giving larger inhibition zones than the reference antibiotics. The antimicrobial efficacy for the MS complexes follows the order: CdS > gentamicin > CuS > NiS > CoS > LaS > AlS > S, whereas MSI complex, potencies are ordered as CuSI > gentamicin > CdSI >NiSI > CoSI > LaSI > AlSI > S. In vitro cytotoxicity screening of MSI complexes disclosed that both CuSI and CdSI exhibited higher activity against human liver (Hep‐G2) and breast (MDA‐MB231) carcinoma cell lines than the reference (cisplatin) drug. The satisfactory bioactivities observed for several of these compounds supports the underlying design idea for combining important bioactive motifs for possible therapeutic benefit.