A novel azo metal complexes of 5, 5, 7-trimethyl-4, 5, 6, 7-tetrahydro-1, 3-benzothiazol as potential pharmacological agents: Synthesis and spectroscopic characterization

Matada, Mallikarjuna Niluvanji; Keshavayya, J.

doi:10.1016/j.molstruc.2018.11.081

Cited by 14 publications

(14 citation statements)

References 42 publications

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“…[2] This class of compounds comprises nearly 60-70% of the commercial dyes produced worldwide. [3] Azo-dyes derived from aromatic amines and their metal complexes have widespread applications in various fields. They are the subject of many research works because of their applications as textile dyes, pharmaceutical materials and indicators.…”

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 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: 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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“…Synthesis of azo dye ligand 71 was achieved via diazo-coupling reaction between 5,5,7-trimethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-2-amine 69 and 2-thioxodihydropyrimidine-4,6(1 H ,5 H )-dione 70 at 0–10 °C (Scheme 19, Table 15). 57…”

Section: Recent Synthesis Of Benzothiazole Based Anti-tubercular Mole...mentioning

confidence: 99%

Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

et al. 2023

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“…In this regard, reported novel series of azo disperse dyes via diazo-coupling reaction at 0–5 °C between 5,5,7-trimethyl-4,5,6,7-tetrahydro-1, 3-benzothiazol-2-amine and 2-thioxodihydropyrimidine-4,6(1 H ,5 H )-dione ( Scheme 5 ). The facile approach resulted in excellent yields [ 55 ]. Another example of diazo-coupling reaction method to synthesize new series of benzothiazole with substituted pyridone/pyrazole as coupling agent is reported [ 56 ].…”

Section: Therapeutic Potential Of Azo Moietymentioning

confidence: 99%

“…Therefore, recent studies are focused on the design and synthesis of the nitrogen- and sulfur-containing heterocyclic azo dyes and their metal chelates due to the decreased toxicity, excellent and versatile biological properties, such as its antimalarial, antitubercular, anti-inflammatory, anti-leishmanial and anti-oxidant effects [ 66 , 67 ]. The metal complexes, Cu(II) and Fe(III), of azo dyes derived from benzothiazole are pharmacologically effective against the drug-resistant strain of M. tuberculosis (MIC value 1.6 µg/mL) and matrix metallo-protein enzymes (88–95% inhibition) [ 55 ]. Similarly, the metal complexes; Zn(II), Co(II) and Cu(II) of azo-azomethine ligands were found to possess more efficient in vitro proliferation inhibitory potential against non-small lung cancer and prostate cancer compared to the parent ligands [ 68 ] and the metal salts; Co(II), Cu(II) and Ni(II) of 4-amino antipyrine azo derivatives were screened in vitro for the cytotoxic potential.…”

Section: Therapeutic Potential Of Azo Moietymentioning

confidence: 99%

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

et al. 2021

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Synthetic heterocyclic compounds have incredible potential against different diseases; pyridines, phenolic compounds and the derivatives of azo moiety have shown excellent antimicrobial, antiviral, antidiabetic, anti-melanogenic, anti-ulcer, anticancer, anti-mycobacterial, anti-inflammatory, DNA binding and chemosensing activities. In the present review, the above-mentioned activities of the nitrogen-containing heterocyclic compounds (pyridines), hydroxyl (phenols) and azo derivatives are discussed with reference to the minimum inhibitory concentration and structure–activity relationship, which clearly indicate that the presence of nitrogen in the phenyl ring; in addition, the hydroxyl substituent and the incorporation of a diazo group is crucial for the improved efficacies of the compounds in probing different diseases. The comparison was made with the reported drugs and new synthetic derivatives that showed recent therapeutic perspectives made in the last five years.

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A novel azo metal complexes of 5, 5, 7-trimethyl-4, 5, 6, 7-tetrahydro-1, 3-benzothiazol as potential pharmacological agents: Synthesis and spectroscopic characterization

Cited by 14 publications

References 42 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

Recent advances in the synthesis of new benzothiazole based anti-tubercular compounds

Pyridine Scaffolds, Phenols and Derivatives of Azo Moiety: Current Therapeutic Perspectives

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