Synthesis, characterization, pharmacological and computational studies of 4, 5, 6, 7-tetrahydro-1, 3-benzothiazole incorporated azo dyes

Maliyappa, M.R.; Keshavayya, J.; Mallikarjuna, N.M.; Krishna, P. Murali; Shivakumara, N.; Telkar, Sandeep; Sailaja, Krishnamurty; Nazrulla, Mohammed Azeezulla

doi:10.1016/j.molstruc.2018.11.041

Cited by 55 publications

(17 citation statements)

References 73 publications

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“…The second peak appeared at 386 nm which related to n-π* transition of (N=N) azo group in the free ligand. [46,47] This peak was shifted in all metal complex spectra in the region of 351-383 nm, which indicated the participation of the azo group in coordination.…”

Section: Uv-visible Spectra Of the Azo-dye Ligand And Its Metal Commentioning

confidence: 91%

“…[8] Among these compounds, heterocyclic azo-dyes and their metal complexes can be involved in biological reactions like nitrogen fixation and RNA inhibition, in cosmetics as well as in non-linear optics protein synthesis. [9,10] 4,4 0 -Oxydianiline is useful compound as it can be used in the production of polyimide, poly(ester) imide, poly(amide)imide resins, poly(imideurea)s and aromatic polyether imides. [11] The resins produced have temperature-resistant properties.…”

Section: Introductionmentioning

confidence: 99%

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Metal complexes of tetradentate azo‐dye ligand derived from 4,4′‐oxydianiline: Preparation, structural investigation, biological evaluation and MOE studies

Deghadi

Mahmoud

Mohamed

2020

Applied Organom Chemis

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The Cr (III), Mn (II), Fe (III), Co (II), Ni (II), Cu (II) and Cd (II) complexes were prepared by reaction of its metal chlorides with new azo‐dye ligand (H2L). The ligand derived from 4,4′‐oxydianiline and 2‐amino‐4‐chlorophenol was synthesized in a 1:2 molar ratio. The structure of the ligand and its metal complexes was investigated using different tools such as elemental analysis (C, H, N and M), molar conductivity, IR, UV–vis, 1H‐NMR, mass spectrometry and thermogravimetric and differential thermogravimetric studies. The data showed that the ligand acted as a N,N,O,O‐binegative tetradentate ligand. All metal complexes had a octahedral structure as depicted by spectral and elemental analyses. The conductivity data showed the electrolytic nature of the Cr (III) and Fe (III) complexes while the other complexes were nonelectrolytes. Thermal analysis studies showed the decomposition of the complexes in four to five steps with the weight loss of hydrated water in the first decomposition step followed by the coordinated water and ligand molecules. Biological activity was tested for the prepared compounds against four bacterial species (Bacillus subtilis, Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa) and against two fungal species (Aspergillus fumigatus and Candida albicans). Also, all complexes were screened for anticancer activities against a breast cancer (MCF‐7) cell line. The [Co(L)(H2O)2] complex showed the lowest IC50 value. Molecular docking is a key tool in computer drug design. Therefore, investigation of protein receptors and ligand interaction plays a vital role in the design of structurally based drugs. As a result, docking studies were investigated for H2L ligand, [Mn(L)(H2O)2] and [Ni(L)(H2O)2] complexes with 5KBC, 3V7B and 4G9M receptors.

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Section: Uv-visible Spectra Of the Azo-dye Ligand And Its Metal Commentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Metal complexes of tetradentate azo‐dye ligand derived from 4,4′‐oxydianiline: Preparation, structural investigation, biological evaluation and MOE studies

Deghadi

Mahmoud

Mohamed

2020

Applied Organom Chemis

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“…The results obtained in the waste characterization by FTIR after both processes showed the transformation of complex functional groups into simpler ones. Aromatic functional groups be transformed to the CH 3 group in the range of 1023-1093 cm −1 in Terasil Blue dye and 2850-3000 cm −1 in Erionyl Blue dye [46][47][48], and the decrement of toxic-type azo groups in the range of 1634 cm −1 [46,49], contributing to mineralization.…”

Section: Discussion Of the Resultsmentioning

confidence: 99%

Blue dye degradation in an aqueous medium by a combined photocatalytic and bacterial biodegradation process

Pérez-Osorio¹,

HernÁndez-GÓmez²,

Arriola-Morales³

et al. 2020

Turk J Chem

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This paper aimed at implementing a treatment system for polluted water with textile dyes, starting with a photocatalytic decomposition process using sunlight as a source of energy and continuing with a bacterial biodegradation process, in order to reach degradation percentages higher than those obtained using only one of the processes mentioned above. When water treatment with the dye in the combined system was over, an acute ecotoxicity test was performed to make sure that toxic metabolites were not produced due to biodegradation. Solophenyl Blue azoic dye, and Erionyl Blue and Terasil Blue anthraquinone dye-colored solutions were treated with the Pd/Al 80 Ce 10 Zr 10 catalyst in a solar collector for the photocatalytic process. On the other hand, the waste dye, which was obtained from photocatalysis with a bacterial consortium from polluted areas by metals and hydrocarbons in aerobic conditions, was inoculated for biodegradation. Biodegradation was obtained for the dyes after both processes as 90.91% for the Solophenyl Blue azoic dye, and 87.80% and 87.94%, respectively, for the Erionyl Blue and Terasil Blue anthraquinone dyes. After the degradation processes, it was proven, via an ecotoxicity test with Daphnia magna, that toxic metabolites had not been produced.

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“…The targeted diaryl aromatic azo compounds were synthesised by the facile diazo-coupling approach (Scheme 1) described previously in literature [45][46][47][48] . The combination of the substituted amines (4-nitro aniline, p-toluidine and 3-amino,2-chloro pyridine) with phenol derivatives (resorcinol, a-naphthol and b-naphthol) produced azo-phenol compounds in moderate to good yields (40-80%).…”

Section: Chemistrymentioning

confidence: 99%

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

Tahir

Shahzad

Tabassum

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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In the present study, a series of azo derivatives (TR-1 to TR-9) have been synthesised via the diazo-coupling approach between substituted aromatic amines with phenol or naphthol derivatives. The compounds were evaluated for their therapeutic applications against alpha-glucosidase (anti-diabetic) and pathogenic bacterial strains E. coli (gram-negative), S. aureus (gram-positive), S. aureus (gram-positive) drug-resistant strain, P. aeruginosa (gram-negative), P. aeruginosa (gram-negative) drug-resistant strain and P. vulgaris (gram-negative). The IC 50 (mg/mL) of TR-1 was found to be most effective (15.70 ± 1.3 mg/mL) compared to the reference drug acarbose (21.59 ± 1.5 mg/mL), hence, it was further selected for the kinetic studies in order to illustrate the mechanism of inhibition. The enzyme inhibitory kinetics and mode of binding for the most active inhibitor (TR-1) was performed which showed that the compound is a noncompetitive inhibitor and effectively inhibits the target enzyme by binding to its binuclear active site reversibly.

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Synthesis, characterization, pharmacological and computational studies of 4, 5, 6, 7-tetrahydro-1, 3-benzothiazole incorporated azo dyes

Cited by 55 publications

References 73 publications

Metal complexes of tetradentate azo‐dye ligand derived from 4,4′‐oxydianiline: Preparation, structural investigation, biological evaluation and MOE studies

Metal complexes of tetradentate azo‐dye ligand derived from 4,4′‐oxydianiline: Preparation, structural investigation, biological evaluation and MOE studies

Blue dye degradation in an aqueous medium by a combined photocatalytic and bacterial biodegradation process

Diaryl azo derivatives as anti-diabetic and antimicrobial agents: synthesis, in vitro, kinetic and docking studies

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