Synthesis, characterization, computational and biological studies of nitrothiazole incorporated heterocyclic azo dyes

Vinodkumar,; Keshavayya, J.; Pushpavathi, Itte; Keerthikumar, C. T.; Maliyappa, M.R.; Ravi, B. N.

doi:10.1007/s11224-020-01493-0

Cited by 17 publications

(9 citation statements)

References 35 publications

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“…Regarding the zinc complex, Zn (CEIH) 2 , there are two UV-Vis bands, the first band is at λ max = 392.74 nm (E = 3.156 eV, f = 0.364) which attributed to The proposed skeletons of the synthesized NCCD and Zn (CEIH) 2 can be also supported by 1 H-NMR and 13 C-NMR theoretical analysis (Figures S9 and S10) and compared with the experimental data. In the case of 1 H-NMR for organic product NCCD, there is an agreement between experimental results and theoretical data.…”

Section: Uv-visible Analysis (Td-dft Studies)mentioning

confidence: 67%

“…The 1 H-NMR spectrum of NCCD ligand showed singlet signal at δ Η 13.01 ppm assigned to the NH proton. Its low-field position indicates the existence of hydrogen bonding that is confirmed by its disappearance in deuterated 1 HNMR spectra, Figure S3. The multiple signals at δ Η 7.5-7.35 ppm are attributed to phenyl ring.…”

Section: H and 13 C-nmr Spectramentioning

confidence: 78%

“…The product was achieved by drop-wise addition of 20-ml methanolic solution of Zn (CH 3 COO) 2 .2H 2 O (0.05475 g, 0.25 mmol) into 20 ml of ethanolic solution of (NCCD [1]) (0.2045 g, 1.0 mmol) during stirring. The mixture was refluxed for 3 h. The color of the mixture showed a gradient shifting from yellow to red by time.…”

Section: (Acdpc)mentioning

confidence: 99%

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Zinc(II)‐facilitated nucleophilic addition on N‐(4‐chlorophenyl) carbon hydrazonoyl dicyanide and hybrid complex formation: X‐ray, spectral characteristics, DFT, molecular docking, and biological studies

Elbadawy

El‐Dissouky

Elkashef

et al. 2022

Applied Organom Chemis

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The isolated crystalline, N-(4-chlorophenyl) carbonohydrazonoyl dicyanide, NCCD, showed a unique behavior in the presence of zinc ions, ethanol, and H 2 O. The product was proved to be a two-unit complex consisting of coordinated zinc(II) complex part, bis-. Such behavior may be attributed to the activity of nitrile groups in NCCD and the zinc(II) catalytic power in aqueous media. The structures of the products were confirmed by elemental analysis and single-crystal X-ray analysis. The spectral properties were analyzed by studying FTIR, UV-Visible, 1 H NMR, 13 C NMR, and XPS. Moreover, computational calculations including DFT were applied to the synthesized compounds to estimate their optimized structure and deduce some quantum parameters. The FTIR, UV-Visible, and NMR data were compared with the calculated results, showing a good agreement. Molecular docking was applied to study the interaction of NCCD and GNB-selected protein targets for Escherichia coli (ID: 5I39) and Proteus vagaries (ID: 6QF6). The isolated compounds were investigated as antibacterial, antioxidant, and anticancer agents showing variable activities.The NCCD showed a higher impact as an antimicrobial and anticancer agent, whereas the zinc complex showed better antioxidant behavior using DPPH radical scavenging activity test.

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Section: Uv-visible Analysis (Td-dft Studies)mentioning

confidence: 67%

Section: H and 13 C-nmr Spectramentioning

confidence: 78%

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Zinc(II)‐facilitated nucleophilic addition on N‐(4‐chlorophenyl) carbon hydrazonoyl dicyanide and hybrid complex formation: X‐ray, spectral characteristics, DFT, molecular docking, and biological studies

Elbadawy

El‐Dissouky

Elkashef

et al. 2022

Applied Organom Chemis

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“…If the gap is large, then the promotion of electron becomes difficult and requires lot of energy, so that the molecules become more stable towards any reaction. Thus, from the above discussion it is inferred that the theoretical modeling is most useful in the interpretation of chemical reactivity, kinetic stability, polarizability and biological properties of the molecules [38,39,40].…”

Section: Energy Gapðδeþ ¼ E Homo à E Lumomentioning

confidence: 99%

Synthesis, characterization and biological investigations of potentially bioactive heterocyclic compounds containing 4-hydroxy coumarin

Nagaraja

Bodke

Pushpavathi

et al. 2020

Heliyon

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In this paper, we have reported the synthesis of a series of heterocyclic azo dyes containing 4-hydroxy coumarin by diazo-coupling reaction. The structural aspect of the newly synthesized compounds was accomplished by various physico-chemical techniques like UV-Visible, FT-IR, NMR, and mass spectrometry. The computational calculations and geometrical optimization of the newly synthesized azo dyes were investigated by using Gaussian software with the help of Density functional theory (DFT)/B3LYP method using 6-31G(d,p) basis set at gaseous phase. Also, the quantum chemical parameters were evaluated to understand the structural activity concept of the dyes. The pharmacological efficacy of the azo dyes was investigated by antimicrobial, antitubercular, DNA cleavage and in silico molecular docking studies. All the newly synthesized compounds were able to exhibit significant inhibitory activity against tested microbes. Further, the in silico molecular docking showed effective binding properties of the compounds against RpsA target receptor.

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“…Nowadays, the heterocyclic azo compound has become very popular because of its superior strength, stability, light fastness, wash fastness, and also produces a remarkable bathochromic effect relative to the simple aromatic carbocyclic system . The existence of azo linkages in the heterocyclic architecture claims plenty of pharmacological applications like antimicrobial, antiviral, antioxidant, antituberculosis, anti‐inflammatory, anticancer, protein synthesis, nitrogen fixation, DNA binding, and cleavage studies …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Potency of Butyl‐Pyridone Based Azo Dyes

et al. 2020

Self Cite

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A series of heterocyclic disperse azo dyes having pyridone architecture was prepared by a simple, economical and highly efficient diazo-coupling method. In this method, butyl pyridone was used as a common coupling component by changing the five heterocyclic amine moieties. The structural investigations of the analogous compounds were accomplished by various spectroscopic techniques. Further, all the azo dyes were examined for their potency towards antibacterial, antituberculosis and anticancer activities. The results revealed that all the dye molecules exhibited excellent tuberculosis activity and also very promising anticancer activity. In the case of the antibacterial assay, only a few azo dyes displayed good inhibition effect towards the tested bacterial strains.[a] Dr.

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Synthesis, characterization, computational and biological studies of nitrothiazole incorporated heterocyclic azo dyes

Cited by 17 publications

References 35 publications

Zinc(II)‐facilitated nucleophilic addition on N‐(4‐chlorophenyl) carbon hydrazonoyl dicyanide and hybrid complex formation: X‐ray, spectral characteristics, DFT, molecular docking, and biological studies

Zinc(II)‐facilitated nucleophilic addition on N‐(4‐chlorophenyl) carbon hydrazonoyl dicyanide and hybrid complex formation: X‐ray, spectral characteristics, DFT, molecular docking, and biological studies

Synthesis, characterization and biological investigations of potentially bioactive heterocyclic compounds containing 4-hydroxy coumarin

Synthesis, Characterization and Biological Potency of Butyl‐Pyridone Based Azo Dyes

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