Design, synthesis, antimicrobial activity and computational studies of novel azo linked substituted benzimidazole, benzoxazole and benzothiazole derivatives

Mishra, Virendra; Ghanavatkar, Chaitannya W.; Mali, Suraj N.; Qureshi, Shahnawaz I.; Chaudhari, Hemchandra K.; Sekar, Nagaiyan

doi:10.1016/j.compbiolchem.2019.01.003

Cited by 108 publications

(51 citation statements)

References 29 publications

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“…The IR spectrum of the ligand showed a broad band of (OH) stretching at 3432 cm −1 that corresponded to the phenolic band. [21,22] The azo group (-N=N-) appeared at 1661 cm −1 . [23] This indicated that the ligand preparation was done in good form.…”

Section: Characterization Of Azo-dye Ligand (H 2 L)mentioning

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: Characterization Of Azo-dye Ligand (H 2 L)mentioning

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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“…We have also modified 5‐amino derivatives of HBT, HBO and HBI to synthesized six azo derivatives using diazotization and coupling reaction, among which VR(16‐19) containing HBT and HBI moiety are emissive in orange to deep red region. It has been evaluated for in‐vitro antibacterial activity against S. aureus and E. coli strains by Resazurin microtiter assay method (REMA) and the exhibit moderate antibacterial activities . The above azo dyes were applied on polyester fabric and evaluated their fastness property, ultraviolet protection factor (UPF), K/S values, and the antibacterial activities.…”

Section: Synthetic and Photophysical Methodologies For Orange To Red mentioning

confidence: 99%

Towards NIR‐Active Hydroxybenzazole (HBX)‐Based ESIPT Motifs: A Recent Research Trend

2020

Self Cite

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In this review, we have explored the synthetic strategies adopted for designing the hydroxybenzazoles (imidazole, oxazole, and thiazole) i. e. HBX derivatives which show emission in red and NIR region. Further, we have examined the effect of different substituents i. e. either directly attached or with extended conjugation on a phenolic ring/ phenyl ring of heterocycles to achieve a red to NIR shift in emission. Finally, we have investigated the applications and computational methodologies adopted for red to NIR emitting dyes. In the future, this review will help to design, synthesized and examine the applications of new derivatives of HBX which will show emission in red to NIR region.

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“…Recently, Guo et al [11] has excellently reviewed antibacterial potential of isatin derivatives. Intriguingly, azo linked substituted benzimidazole, benzoxazole, and benzothiazole synthesized by Mishra et al [12] through diazo coupling also exhibited in vitro antibacterial activity against Staphylococcus aureus and Escherichia Coli strains. Mannich bases of benzimidazole derivatives have also shown in vitro antibacterial activity against Bacillus subtilis, Bacillus pumilus, Escherichia coli and Pseudomonas aeruginosa organisms [13].…”

Section: Biological Activitymentioning

confidence: 99%

Synthesis and pharmacological screening of new isatin-3-[N2-(benzimidazol-1- acetyl)]hydrazone

Chaithanya¹,

Kasiviswanath²,

Chary³

2019

Bull. Chem. Soc. Eth.

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Twenty new isatin-3-[N 2 -(benzimidazol-1-acetyl)]hydrazones (IV) were synthesized from ten different isatin-3-[N 2 -(chloroacetyl)] hydrazones (III) by reacting with benzimidazole and 2-methyl benzimidazole. The intermediates were obtained from isatin hydrazones (II) on condensation with chloroacetyl chloride. These compounds were characterized by IR, 1 H NMR and mass spectra. All the compounds were screened for antimicrobial, antioxidant and cytotoxic activity. Some of the new compounds showed promising antibacterial and antifungal activity.

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Design, synthesis, antimicrobial activity and computational studies of novel azo linked substituted benzimidazole, benzoxazole and benzothiazole derivatives

Cited by 108 publications

References 29 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

Towards NIR‐Active Hydroxybenzazole (HBX)‐Based ESIPT Motifs: A Recent Research Trend

Synthesis and pharmacological screening of new isatin-3-[N2-(benzimidazol-1- acetyl)]hydrazone

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