Synthesis and characterization of a new aroylhydrazone ligand and its cobalt(III) complexes: X-ray crystallography and in vitro evaluation of antibacterial and antifungal activities

Mathews, Nimya Ann; Jose, Anitha; Kurup, M.R. Prathapachandra

doi:10.1016/j.molstruc.2018.10.061

Cited by 29 publications

(15 citation statements)

References 31 publications

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“…The reactions of the ligand precursor 4-benzyloxybenzoylhydrazine (2) with different aromatic aldehydes (cinnamaldehyde, 2-hydroxybenzaldehyde, 2,4-dimethoxybenzaldehyde,4-N,N-dimethylaminobenzaldeh yde, 4-methoxybenzaldehyde) formed the ligands (3)(4)(5)(6)(7). The ligands react with cadmium acetate formed the complexes (8-12) according to Figure 1.…”

Section: Resultsmentioning

confidence: 99%

“…Table 2. Infrared, UV-visible spectral data of the ligands and complexes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12). 1 1660 2 3292, 3190 1640 3 3240 1712 1605 275 4 3286 1674 1605 280 300 328 5 3210 1713 1604 273 320 6 3186 1635 1605 270 342 374 7 3178 1713 1605 275 315 380 8 1598 509 663 295 324 390 9 1574 501 586 305 332 406 10 1566 470 509, 604 308 328 405 11 1574, 1604 516 617 305 365 400 12 1620, 1566 532 663 308 375 405 The 1 H NMR spectral data of the ligands and complexes are shown in the Table 3.…”

Section: Resultsmentioning

confidence: 99%

“…All the reagents were of AR grade and the solvents were purified by standard methods [3]. The ligand precursor (2) and the ligands (3)(4)(5)(6)(7) were synthesized according to a known method [3]. IR spectra were taken as KBr disc using a Shimadzu FTIR-8101 spectrometer from 4000-250 cm -1 .…”

Section: Methodsmentioning

confidence: 99%

“…Hydrazones are an important class of Schiff base ligands which exhibit several applications in pharmaceutical field due to their biological activities including antimicrobial, antifungal, antitumor, antitubercular properties [1][2][3][4][5]. Aroylhydrazones have been widely used as ligands in the preparation of a variety of transition metal complexes [6][7][8][9][10][11]. The aroylhydrazone moiety may coordinate to the metal through the keto or enol forms [3,12].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Bioactive Cadmium (II) Complexes Derived from 4-Benzyloxybenzoylhydrazine with Different Aromatic Aldehydes

Ansary¹,

Mamun²,

Howlader³

2020

SJC

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The reactions of the ligand precursor 4-benzyloxybenzoylhydrazine (2) with cinnamaldehyde, salicylaldehyde, 2,4-dimethoxybenzaldehyde, 4-N,N dimethylaminobenzaldehyde, 4-methoxybenzaldehyde formed the ligands C 6 H 5 CH 2 OC 6 H 4 CONHN=CHR, where R=C 6 H 5 CH=CH, (3); C 6 H 4 (OH), (4); C 6 H 3 (OCH 3) 2 , (5); C 6 H 4 N(CH 3) 2 , (6); C 6 H 4 (OCH 3), (7), respectively. The ligand precursor 4-benzyloxybenzoylhydrazine (2) was synthesized by the condensation reaction of ethyl-4-benzyloxybenzoate (1) with hydrazine hydrate. Ethyl-4-benzyloxybenzoate (1) was synthesized by the reaction of ethyl-4-hydroxybenzoate and benzyl bromide dissolved in acetone in presence of anhydrous potassium carbonate. By the reactions of the synthesized ligands with cadmium(II) acetate, a series of complexes [(C 6 H 5 CH 2 OC 6 H 4 CONHN=CHR) 2 Cd] were obtained, where R=C 6 H 5 CH=CH, (8); C 6 H 4 (OH), (9); C 6 H 3 (OCH 3) 2 , (10); C 6 H 4 N(CH 3) 2 , (11); C 6 H 4 (OCH 3), (12). The complexes cannot be obtained via a template method. The compounds have been characterized by elemental analysis, conductivity measurements, UV-visible, FT-IR, 1 H NMR spectral studies. The conductivity measurement data revealed that the complexes are non-electrolytic in nature. The UV-visible data of the complexes suggested the tetrahedral geometry of Cd(II) ion. The antibacterial results of the ligands (3-7) exhibited very low or no activity against pathogenic bacteria viz. gram positive (Bacillus anthracis, Staphylococcus aureus, Bacillus megaterium) and gram negative (Shigella flexneri, Escherichia coli, Shigella shiga), whereas their corresponding complexes (8-12) exhibited activity against the aforementioned bacteria but less than the standard drug, kanamycine. This implies that the activity showed by the complexes is solely responsible for the presence of Cadmium (II) ion.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Characterization of Bioactive Cadmium (II) Complexes Derived from 4-Benzyloxybenzoylhydrazine with Different Aromatic Aldehydes

Ansary¹,

Mamun²,

Howlader³

2020

SJC

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“…Additional features include its ease of performance, accuracy and selectivity [12]. Aroylhydrazones play a significant role in coordination chemistry and they represent an important class of NO donors [13,14]. They have been used for separation and preconcentration of some [14,15].…”

Section: Introductionmentioning

confidence: 99%

Cloud point extraction procedure for preconcentration of Co2+, Ni2+ and Cu2+ from water and biological samples using a thiosemicarbazone derivative as a complexing agent.

et al. 2021

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An accurate and simple preconcentration procedure was presented for cloud point extraction of Co 2+ , Ni 2+ and Cu 2+ from water, blood and urine samples. The procedure based on complexation of the metal ions with (E)-2-(2,4-dihydroxybenzylidene)-Nphenylhydrazine-1-carbothioamide (DHBPHC) and subsequent extraction into a surfactant-rich phase of Triton X-114. The optimized procedure (50 mL solution; pH 6; 1 × 10 -4 mol L -1 of DHBPHC; 0.08% (v/v) Triton X-114) exhibits linear range up to 500 µg L -1 and limit of detection of 0.34, 0.94 and 0.83 µg L -1 for Co 2+ , Ni 2+ and Cu 2+ , respectively. Most potentially interferants did not impact the extraction process. The procedure was applied for preconcentration and determination of Co 2+ , Ni 2+ and Cu 2+ in water, blood and urine by flame atomic absorption spectrometry.

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Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N⁴‐cyclohexylthiosemicarbazone

Mathews

Begum

Kurup

2019

Applied Organom Chemis

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A 3,5‐dichlorosalicylaldehyde‐N4‐cyclohexylthiosemicarbazone (C14H16Cl2N3OS) and its complexes [Zn(dsct)(phen)]·DMF (1), [Zn(dsct)(bipy)]·DMF (2), [Cu(dsct)(bipy)]·DMF (3) (phen = 1,10‐phenathroline, bipy = 2,2’bipyridine) were synthesized and characterized by CHN analysis, FT‐IR, UV–vis and NMR spectra. The molecular structure of the thiosemicarbazone (H2dsct) and its complexes have been resolved using single crystal XRD studies. In the complexes, thiosemicarbazone exist in the thioiminolate form and acts as dideprotonated tridentate ligand coordinating through phenolic oxygen, thioiminolate sulfur and azomethine nitrogen. The antibacterial activity of the prepared compounds were screened against Escherichia coli, Salmonella typhi, Enterobacter aerogenes, Shigella dysentriae, Bacillus cereus, Staphylococcus aureus. All the complexes showed activity against bacterial strains E.coli and Salmonella typhi. The thiosemicarbazone showed activity against three bacterial strains such as E. coli, Enterobacter aerogenes and Shigella dysentriae. Complex 2 showed very good antibacterial activity as compared to standard drug (Ampicillin) against the bacterial strain, Salmonella typhi. Finally, the thiosemicarbazone and its complexes have been used to accomplish molecular docking studies against an Epidermal Growth Factor Receptor (EGFR) and breast cancer mutant 3hb5‐oxidoreductase to determine the most preferred mode of interaction. The results confirm that the complex [Cu (dsct)(bipy)]·DMF(3) showed the highest docking score as compared to other complexes under study. The [Cu(dsct)(bipy)]·DMF(3) complex was evaluated for their anticancer activities against breast cancer cell line (MCF‐7) and normal L929 (Mouse Fibroblast) cell line. It was found that the compound showed an LC50 of 6.25 μg/mL against breast cancer cell line (MCF‐7).

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Synthesis and characterization of a new aroylhydrazone ligand and its cobalt(III) complexes: X-ray crystallography and in vitro evaluation of antibacterial and antifungal activities

Cited by 29 publications

References 31 publications

Synthesis and Characterization of Bioactive Cadmium (II) Complexes Derived from 4-Benzyloxybenzoylhydrazine with Different Aromatic Aldehydes

Synthesis and Characterization of Bioactive Cadmium (II) Complexes Derived from 4-Benzyloxybenzoylhydrazine with Different Aromatic Aldehydes

Cloud point extraction procedure for preconcentration of Co2+, Ni2+ and Cu2+ from water and biological samples using a thiosemicarbazone derivative as a complexing agent.

Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N⁴‐cyclohexylthiosemicarbazone

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Synthesis and characterization of a new aroylhydrazone ligand and its cobalt(III) complexes: X-ray crystallography and in vitro evaluation of antibacterial and antifungal activities

Cited by 29 publications

References 31 publications

Synthesis and Characterization of Bioactive Cadmium (II) Complexes Derived from 4-Benzyloxybenzoylhydrazine with Different Aromatic Aldehydes

Synthesis and Characterization of Bioactive Cadmium (II) Complexes Derived from 4-Benzyloxybenzoylhydrazine with Different Aromatic Aldehydes

Cloud point extraction procedure for preconcentration of Co2+, Ni2+ and Cu2+ from water and biological samples using a thiosemicarbazone derivative as a complexing agent.

Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N4‐cyclohexylthiosemicarbazone

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Synthesis, characterization, biological screening and molecular docking of Zn(II) and Cu(II) complexes of 3,5‐dichlorosalicylaldehyde‐N⁴‐cyclohexylthiosemicarbazone