Synthesis, structural characterization and biological studies of copper complexes with 2-aminobenzothiazole derivatives

Joseph, J.; Janaki, G. Boomadevi

doi:10.1016/j.molstruc.2014.01.028

Cited by 23 publications

(8 citation statements)

References 26 publications

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“…Also, the synthesis and antibacterial studies of copper(II) complexes of a Knoevenagel condensate of acetoacetanilide (that is obtained from substituted benzaldehydes and acetoacetanilide) and 2‐aminobenzothiazole have been reported. The Cu(II) complex gave a better antibacterial activity compared to the ligand …”

Section: Introductionmentioning

confidence: 99%

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Omaka¹,

Ekennia²,

Njoku³

et al. 2018

Applied Organom Chemis

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Benzothiazole moiety has gained a lot of attention because of its importance as essential pharmacophore in the development of metal based drugs. Nickel (II) and copper(II) complexes of a benzothiazole based ligand, 2,2'-bibenzo[d]thiazole (L 1 ), synthesized by the reaction of benzothiazole-2-carbonylchloride and o-aminothiophenol, is reported. The compounds were characterised by elemental and percentage metal analyses, spectroscopic (FTIR and UV-vis), 1 H and 13 C NMR, Mass spectra, thermal, magnetic moment and molar conductance analyses. The mass spectra, elemental and percentage metal composition of the metal complexes gave a 2:1 ligand to metal stoichiometric mole ratio. The spectral data showed that the ligand was coordinated to the metal ions through the nitrogen atoms of the benzothiazole moiety. The electronic spectra and magnetic susceptibility measurements showed that the nickel and copper complexes adopted square planar geometries. The ligand and its metal(II) complexes were screened against some drug resistant microbes and were found to exhibit varied degree of antimicrobial activities. The nickel complex was more active compared to ciprofloxacin against Staphylococcus aureus and Bacillus cereus. Similarly, the antioxidant potential of the ligand was evaluated. The ligand is a better ferrous ion chelating agent compared to 1,10-phenanthroline and 2,2-bipyridine. The ligand and its complexes exhibited good antimicrobial and Fe 2+ chelating properties making them probable compounds of interest in antibiotic and antioxidant drug researches.

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Section: Introductionmentioning

confidence: 99%

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Omaka¹,

Ekennia²,

Njoku³

et al. 2018

Applied Organom Chemis

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“…[ 17,18 ] Moreover, many Schiff‐base complexes derived from 2‐aminobenzothiazole have been obtained and their biological activities were further investigated. [ 19–21 ] Therefore, it is of great significance to explore the structure of heterocyclic compounds, which will provide a research basis for the further study of their properties.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structure, density functional theory calculations, and antimicrobial activity of silver(I) complex derived from 2‐aminobenzothiazole ligand

Jiang

Lei

et al. 2021

Applied Organom Chemis

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Reaction of silver nitrate with 2‐aminobenzothiazole (abbreviated as Habt) in methanol at 45°C gave mononuclear complex of formula [Ag (Habt)2]NO3•CH3OH. The structure of the complex was characterized by infrared (IR) spectra, single crystal X‐ray diffraction, and elemental analysis. X‐ray diffraction analysis indicated that the title complex was crystallized in the triclinic crystal system with space group P–1, in which silver(I) ion was coordinated to two 2‐aminobenzothiazole ligands through the benzothiazol nitrogen atom. Theoretical study of the complex was carried out by density functional theory (DFT) B3LYP method. The antimicrobial effects of the ligand and its silver(I) complex were evaluated by bio‐microcalorimetry on the growth of Schizosaccharomyces pombe (S. pombe). Some quantitative metabolic parameters, such as growth rate constant (k), maximum heat power (Pmax), inhibition ratio (I), and half inhibition concentration (IC50), were derived from the metabolic power–time curves of S. pombe growth. The half inhibition concentration (IC50) of the ligand was calculated to be 2.58 × 10−3 mol L−1. The complex could strongly influence the lag phase of S. pombe.

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“…A continuous interest in this class of compounds follows nowadays and numerous efforts to synthesize new biologically active heterocyclic compounds derived from the benzothiazole moiety have been made in the last 50 years. Several of these derivatives were found to possess anticonvulsant [27,28,29] and antioxidant [30,31,32] activities. In this context, some results related to molecules containing benzothiazole nuclei in medicinal chemistry have been summarized elsewhere [33,34].…”

Section: Introductionmentioning

confidence: 99%

Isothioureas, Ureas, and Their N-Methyl Amides from 2-Aminobenzothiazole and Chiral Amino Acids

et al. 2019

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In this investigation, the reaction of 2-dithiomethylcarboimidatebenzothiazole with a series of six chiral amino-acids was studied. The reaction proceeds through the isolable sodium salt of SMe-isothiourea carboxylates as intermediates, whose reaction with methyl iodide in stirring DMF as solvent affords SMe-isothiourea methyl esters. The presence of water in the reaction leads to the corresponding urea carboxylates as isolable intermediates, whose methyl esters were obtained. Finally, the urea N-methyl amide derivatives were isolated when SMe-isothiourea or urea methyl esters were reacted with methylamine in the presence of water. The structures of synthesized compounds were established by 1H and 13C nuclear magnetic resonance and the structures of SMe-isothiourea methyl esters derived from (l)-glycine, (l)-alanine, (l)-phenylglycine, and (l)-leucine, by X-ray diffraction analysis. This methodology allows to functionalize 2-aminobenzothiazole with SMe-isothiourea, urea, and methylamide groups derived from chiral amino acids to get benzothiazole derivatives containing coordination sites and hydrogen bonding groups. Further research on the biological activities of some of these derivatives is ongoing.

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Synthesis, structural characterization and biological studies of copper complexes with 2-aminobenzothiazole derivatives

Cited by 23 publications

References 26 publications

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Nickel(II) and copper(II) complexes of 2,2’‐bibenzo[d]thiazole: Synthesis, characterisation and biological studies

Synthesis, crystal structure, density functional theory calculations, and antimicrobial activity of silver(I) complex derived from 2‐aminobenzothiazole ligand

Isothioureas, Ureas, and Their N-Methyl Amides from 2-Aminobenzothiazole and Chiral Amino Acids

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